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

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Synonym	Source
1,3,7-Trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine	biospider
1,3,7-Trimethyl-2,6-dioxopurine	ChEBI
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione	HMDB
1,3,7-Trimethylpurine-2,6-dione	ChEBI
1,3,7-Trimethylxanthine	ChEBI
1-Methyl-theobromine	HMDB
1-Methyltheobromine	ChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion	ChEBI
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

Showing 1 to 10 of 60 entries

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

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-0.07	HANSCH,C ET AL. (1995)
Experimental pKa	10.4
Experimental Water Solubility	21.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	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
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-fa38c865089a3a05f287	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000b-0900000000-0e82732a924c974dd0c8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-bfc94c8091471847482b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-1900000000-c8fcf16986c494898203	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-3900000000-9569e0552abb7ebd145a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-3a924abd44877050c1c9	2017-09-14	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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
(+)-inotropic			DUKE
adenosine antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
analeptic	35337	Any drug that enhances the activity of the central nervous system.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti apneic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti apoptotic			DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE

Showing 1 to 10 of 57 entries

Enzymes

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Showing 1 to 4 of 4 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
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
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 2 of 2 entries

Files

MSDS

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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.