Showing Compound Caffeine (FDB002100)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2019-11-26 02:57:00 UTC

Primary ID

FDB002100

Secondary Accession Numbers

FDB017732

Chemical Information

FooDB Name

Caffeine

Description

Caffeine, also known as coffein or mateina, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Caffeine is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeine is a bitter and odorless tasting compound. Caffeine is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and tea and in a lower concentration in energy drinks, ice cream cones, and other candies. Caffeine has also been detected, but not quantified in, several different foods, such as longans, cornbread, whiskies, american shad, and highbush blueberries. This could make caffeine a potential biomarker for the consumption of these foods. Caffeine is a potentially toxic compound.

CAS Number

58-08-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3,7-Trimethyl-2,6-dioxopurine	ChEBI
1,3,7-Trimethylpurine-2,6-dione	ChEBI
1,3,7-Trimethylxanthine	ChEBI
1-Methyltheobromine	ChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion	ChEBI
7-Methyltheophylline	ChEBI
Anhydrous caffeine	ChEBI
Cafeina	ChEBI
Cafeine	ChEBI
Coffein	ChEBI
Guaranine	ChEBI
Koffein	ChEBI
Mateina	ChEBI
Methyltheobromine	ChEBI
Teina	ChEBI
Thein	ChEBI
Theine	ChEBI
Respia	Kegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione	HMDB
1-Methyl-theobromine	HMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione	HMDB
7-Methyl theophylline	HMDB
Anhydrous caffeine (JP15)	HMDB
Hycomine	HMDB
Lanorinal	HMDB
Methyltheobromide	HMDB
Methylxanthine theophylline	HMDB
Monohydrate caffeine	HMDB
Propoxyphene	HMDB
Merck dura brand OF caffeine	HMDB
Thompson brand 1 OF caffeine	HMDB
Bristol-myers squibb brand OF caffeine	HMDB
Caffedrine	HMDB
Dexitac	HMDB
Percoffedrinol N	HMDB
Pierre fabre brand OF caffeine	HMDB
Republic drug brand OF caffeine	HMDB
Thompson brand 2 OF caffeine	HMDB
Vivarin	HMDB
Coffeinum N	HMDB
Coffeinum purrum	HMDB
Durvitan	HMDB
GlaxoSmithKline brand OF caffeine	HMDB
No doz	HMDB
Percutaféine	HMDB
Quick-pep	HMDB
Seid brand OF caffeine	HMDB
Berlin-chemie brand OF caffeine	HMDB
Passauer brand OF caffeine	HMDB
Quick pep	HMDB
QuickPep	HMDB
1,3,7-Trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine	biospider
3,7-dihydro-1,3,7-Trimethyl-1H-purin-2,6-dion	ChEBI
3,7-dihydro-1,3,7-Trimethyl-1H-purine-2,6-dione	HMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, 9CI	db_source
Anhydrous caffeine (jp15)	HMDB
Caffein	biospider
Cafipel	db_source
Coffeine	db_source
FEMA 2224	db_source

Predicted Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.55	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.83 m³·mol⁻¹	ChemAxon
Polarizability	18.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H10N4O2

IUPAC name

1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

InChI Identifier

InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChI Key

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Isomeric SMILES

CN1C=NC2=C1C(=O)N(C)C(=O)N2C

Average Molecular Weight

194.1906

Monoisotopic Molecular Weight

194.080375584

Classification

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
Purinone
6-oxopurine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Vinylogous amide
Imidazole
Azole
Urea
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine alkaloid (CHEBI:27732 )
trimethylxanthine (CHEBI:27732 )
Purine alkaloids (C07481 )
a small molecule (1-3-7-TRIMETHYLXANTHINE )

Ontology

Physiological effect

Health effect:

Health condition:

Nervous system disorders:

Headache

Psychiatric disorders:

General disorders and administration site conditions:

Fatigue

Gastrointestinal disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Environmental:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Asthma

Role

Indirect biological role:

Mutagen

Environmental role:

Environmental contaminant

Industrial application:

Food and nutrition:

Food additive

Pharmaceutical industry:

Biological role:

Foods

Cocoa and cocoa products

Beverages:

Coffee products

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 49.48%; H 5.19%; N 28.85%; O 16.48%	DFC
Melting Point	Mp 236° (phase transition at 141°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	21.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-0.07	HANSCH,C ET AL. (1995)
Experimental pKa	10.4
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-052f-8900000000-68b5e9aa3404fb3d8d3a	2014-09-20	View Spectrum
GC-MS	Caffeine, 0 TMS, GC-MS Spectrum	splash10-0536-3900000000-a9e112713ffae6dabdaa	Spectrum
GC-MS	Caffeine, 0 TMS, GC-MS Spectrum	splash10-0536-2900000000-8cdcd005b2e7622a02a3	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-052f-0900000000-f1084acfddb240696073	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-05nf-6900000000-8670a644cee5d9de78d4	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0536-3900000000-4430852b279a72e34822	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0006-0900000000-51898e93480e848d7da1	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-2aed5d425b6a95add5db	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0a4l-4900000000-3ff72dace6687d242f1f	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-2ba1fae6e27c7b836984	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-fd859aeb416e320d6379	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0536-3900000000-a9e112713ffae6dabdaa	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0536-2900000000-8cdcd005b2e7622a02a3	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-052f-0900000000-f1084acfddb240696073	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-05nf-6900000000-8670a644cee5d9de78d4	Spectrum
GC-MS	Caffeine, non-derivatized, GC-MS Spectrum	splash10-0536-3900000000-4430852b279a72e34822	Spectrum
Predicted GC-MS	Caffeine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-0900000000-41f36d541d34d2088964	Spectrum
Predicted GC-MS	Caffeine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0900000000-447fc72b2c709e2e18a9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-5e3b29de16ad91c79fe0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-d6f6c52ac36c8f25a500	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-0900000000-cddd24399d942b1ac97c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CI-B (Unknown) , Positive	splash10-0002-0900000000-2aed5d425b6a95add5db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a4l-4900000000-3ff72dace6687d242f1f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0006-1900000000-2ba1fae6e27c7b836984	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positive	splash10-0002-0900000000-63b9ef42a3e8d59e9997	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-185b3d97d8857a0f269d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-0900000000-f8a0c0dd9f5c4a272eaf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-1900000000-dd8e35226d0704aa657d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-01x9-9800000000-70e3b0eb52481c39d191	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001l-9100000000-6d428a5571beb0e3fed4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-98bec16f898808c3de68	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0002-0900000000-b112e4e059e1ecf98c5f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00dr-0900000000-42c6f8fc7b924e9c64f3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-4900000000-a60a480f1340558740a2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-695d910d49fc0beb1d54	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-094879886a2e72bf0c56	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-761710441aa2c1c3ac68	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0900000000-c10af6eda9a9a4094715	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-3900000000-141118b1a93b4d48b2d4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-c8bd8cccb7dd6c66bb42	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-2c8c1760161edd358026	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-5900000000-260de4a79007e853e4bb	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27732

Phenol-Explorer ID

Not Available

DrugBank ID

DB00201

HMDB ID

HMDB01847

CRC / DFC (Dictionary of Food Compounds) ID

CFJ89-C:CFJ89-C

EAFUS ID

441

Dr. Duke ID

CAFFEINE

BIGG ID

Not Available

KNApSAcK ID

C00001492

HET ID

CFF

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1014161

SuperScent ID

Not Available

Wikipedia ID

Caffeine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
(+)-inotropic		An agent that increases the force or energy of muscular contractions, particularly in the heart. It plays a biological role in enhancing cardiac output and is therapeutically used to treat heart failure, cardiogenic shock, and other cardiovascular conditions, improving cardiac function and overall circulation.	DUKE
Adenosine antagonist	48706	An agent that blocks adenosine receptors, increasing alertness and activity. Therapeutically, it is used to treat conditions like narcolepsy, and has potential applications in managing asthma, allergies, and cardiovascular diseases by reducing adenosine's vasodilatory and bronchoconstrictive effects.	DUKE
Analeptic	35337	A central nervous system stimulant that increases alertness and counteracts depression, used therapeutically to treat conditions such as respiratory depression, sedative overdose, and coma, by enhancing brain activity and promoting arousal.	DUKE
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anti-apneic	52217	An agent that stimulates breathing, used to treat respiratory disorders such as apnea, promoting normal respiratory function and preventing oxygen deprivation.	DUKE
Anti-apoptotic		An agent that inhibits programmed cell death, promoting cell survival. It plays a biological role in regulating cell growth and development. Therapeutically, it has applications in cancer treatment, neurodegenerative diseases, and tissue repair. Key medical uses include preventing cell loss in stroke, Alzheimer's, and Parkinson's diseases, as well as in cancer therapy to protect healthy cells from chemotherapy-induced damage.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti carcinogenic	35610	An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.	DUKE
Anti cariogenic	52217	An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.	DUKE
Anti dermatitic	50177	An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.	DUKE
Anti emetic	50919	An agent that prevents or alleviates nausea and vomiting, playing a crucial role in managing chemotherapy-induced, motion-induced, and post-operative nausea. Therapeutically, it helps reduce discomfort and prevent dehydration, commonly used in oncology, gastroenterology, and anesthesia.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-flu	22587	An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.	DUKE
Anti-herpetic	22587	An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.	DUKE
Anti-hypotensive	52217	An agent that increases blood pressure, counteracting hypotension. Its biological role is to stimulate the cardiovascular system, and its therapeutic applications include treating shock, orthostatic hypotension, and severe hypotension. Key medical uses include emergency medicine and critical care.	DUKE
Anti-narcotic		An agent that counteracts the effects of narcotics, used to treat narcotic overdose, manage withdrawal symptoms, and support addiction recovery, by blocking opioid receptors and reducing euphoria and dependence.	DUKE
Anti-obesity	52217	An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-rhinitic	52217	An agent that relieves nasal congestion and allergic rhinitis symptoms, reducing inflammation and histamine release. Therapeutically, it's used to manage rhinitis, sinusitis, and allergic reactions, providing relief from sneezing, runny nose, and itchy eyes.	DUKE
Anti serotonergic	48278	An agent that blocks the action of serotonin, a neurotransmitter involved in mood regulation. It reduces serotonin activity, commonly used in managing schizophrenia, anxiety disorders, and nausea, as well as treating conditions like irritable bowel syndrome and migraine headaches.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Anti-vaccinia	22587	An antibody that neutralizes the vaccinia virus, used to treat complications from smallpox vaccination, such as eczema vaccinatum and progressive vaccinia, by reducing viral replication and promoting healing.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Apoptotic		An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.	DUKE
Arrhythmigenic	38070	An agent that induces or exacerbates irregular heart rhythms, often used in medical research to study cardiac arrhythmias. Therapeutically, it has limited applications, but can be used to test the efficacy of anti-arrhythmic medications or in cardiac stress tests to diagnose underlying heart conditions.	DUKE
cAMP-phosphodiesterase inhibitor	23924	An agent that blocks the breakdown of cyclic adenosine monophosphate (cAMP), increasing its levels and enhancing cellular signaling. Therapeutically, it is used to treat respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD), as well as certain cardiovascular conditions.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Cardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.	DUKE
Catabolic		A biological process that breaks down molecules, releasing energy used to fuel anabolic reactions. Therapeutically, catabolic agents are used to manage weight loss, treat metabolic disorders, and enhance athletic performance. Key medical uses include	DUKE
cGMP-phosphodiesterase inhibitor	23924	An agent that blocks the breakdown of cyclic guanosine monophosphate (cGMP), increasing its levels. It relaxes smooth muscle, dilates blood vessels, and improves cardiac function. Therapeutically used to treat erectile dysfunction, pulmonary hypertension, and heart failure, improving exercise tolerance and quality of life.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Central nervous system stimulant	35470	An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.	DUKE
Coronarydilator		An agent that dilates coronary vessels, increasing blood flow to the heart. Its biological role is to reduce cardiac workload and improve oxygen delivery. Therapeutically, it's used to treat angina, myocardial infarction, and other cardiovascular conditions, improving cardiac function and reducing symptoms.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Energizer		An agent that stimulates energy production, enhancing physical and mental activity. Its biological role involves increasing cellular metabolism. Therapeutically, it is used to treat fatigue and lethargy. Key medical uses include managing chronic fatigue syndrome, improving cognitive function, and enhancing athletic performance.	DUKE
Ergotamine enhancer		An agent that stimulates production of ergotamine, a vasoconstrictor used to treat migraine headaches and other vascular disorders by reducing blood flow to affected areas.	DUKE
Name	48318	flavor	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Hypertensive		An agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.	DUKE
Hypoglycemic	35526	An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.	DUKE
Insecticide	24852	An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.	DUKE
Lypolytic		An agent that breaks down fats, playing a biological role in lipid metabolism. Therapeutically, it has applications in managing obesity and hyperlipidemia. Key medical uses include reducing fat deposits, improving cardiovascular health, and treating conditions associated with excessive fat accumulation.	DUKE
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	DUKE
Neurotoxic	50910	A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phosphodiesterase inhibitor	23924	An agent that blocks phosphodiesterase enzymes, increasing cyclic nucleotide levels, and enhancing cellular signaling. Therapeutically, it treats respiratory, cardiovascular, and neurological disorders, with key medical uses including managing erectile dysfunction, pulmonary hypertension, and chronic obstructive pulmonary disease (COPD).	DUKE
Pyrogenic		An agent that induces fever, stimulating the immune system. It plays a biological role in fighting infection and has therapeutic applications in immunotherapy and vaccine development. Key medical uses include treating certain infections and cancers, as well as stimulating the immune system in immunocompromised patients.	DUKE
Respirastimulant		An agent that stimulates an increase in tidal volume and respiratory rate, playing a biological role in enhancing respiratory function. Therapeutically, it is used to manage respiratory disorders, with key medical applications including treatment of chronic obstructive pulmonary disease (COPD), respiratory failure, and apnea.	DUKE
Spasmogenic		An agent that induces spasms, causing sudden involuntary muscular contractions. It plays a biological role in stimulating muscle activity. Therapeutically, it has applications in diagnosing and treating muscle disorders. Key medical uses include assessing muscle function and treating conditions like muscle atrophy, with potential applications in physical therapy and rehabilitation.	DUKE
Stimulant		An agent that enhances alertness, wakefulness, and physical activity by increasing brain activity. Therapeutically, it is used to treat attention deficit hyperactivity disorder (ADHD), narcolepsy, and certain cases of depression, improving focus, attention, and overall mental performance.	DUKE
Tachycardic	38070	An agent that increases heart rate, playing a biological role in stress response and exercise. Therapeutically, it is used to manage bradycardia (abnormally slow heart rate) and cardiac arrest. Key medical uses include treating symptomatic bradycardia, Adams-Stokes syndrome, and asystole, helping to restore normal heart rhythm and maintain adequate blood circulation.	DUKE
Teratogenic	50905	An agent that causes abnormal fetal development, disrupting embryonic growth and leading to birth defects. Its biological role is associated with developmental toxicity, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.	DUKE
Topoisomerase-II inhibitor	50750	An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.	DUKE
Topoisomerase-I inhibitor	50276	An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.	DUKE
Vasodilator	35620	An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.	DUKE
Serine/threonine kinase inhibitor	50925	An agent that blocks the activity of serine/threonine kinases, enzymes involved in cell signaling and division. It has therapeutic applications in cancer, neurodegenerative, and inflammatory diseases, with key medical uses including cancer treatment and managing neurological disorders.	CHEBI
Psychotropic	35471	An agent that affects mood, cognition, and behavior by altering brain chemistry. Its biological role involves modifying neurotransmitter activity. Therapeutically, it's used to manage mental health disorders, with key medical applications including treating anxiety, depression, psychosis, and mood disorders, as well as attention deficit hyperactivity disorder (ADHD).	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Cytochrome P450 2D6	CYP2D6	Q6NWU0
Adenosine receptor A1	ADORA1	P30542
Adenosine receptor A2a	ADORA2A	P29274

Pathways

Name	SMPDB Link	KEGG Link
Caffeine Metabolism	SMP00028	map00232

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.