Showing Compound Theophylline (FDB000453)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2019-11-26 02:54:50 UTC

Primary ID

FDB000453

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Theophylline

Description

Theophylline, also known as uniphyl or aerolate, 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. Theophylline is an extremely weak basic (essentially neutral) compound (based on its pKa). Theophylline is a bitter tasting compound. Theophylline is found, on average, in the highest concentration within cocoa beans and tea. Theophylline has also been detected, but not quantified in, several different foods, such as arabica coffee, guarana, lemons, pummelo, and robusta coffee. This could make theophylline a potential biomarker for the consumption of these foods. Theophylline is a potentially toxic compound.

CAS Number

58-55-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1,3 Dimethylxanthine	HMDB
1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine	biospider
1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione	biospider
1,3-Dimethyl-3,9-dihydro-1H-purine-2,6-dione	biospider
1,3-Dimethyl-7H-purine-2,6-dione	ChEBI
1,3-Dimethylxanthine	ChEBI
1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-	biospider
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-	biospider
2,6-Dihydroxy-1,3-dimethylpurine	biospider
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione	HMDB

Showing 1 to 10 of 168 entries

Predicted Properties

Property	Value	Source
Water Solubility	22.9 g/L	ALOGPS
logP	-0.26	ALOGPS
logP	-0.77	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.93 m³·mol⁻¹	ChemAxon
Polarizability	16.86 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

C7H8N4O2

IUPAC name

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

InChI Identifier

InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)

InChI Key

ZFXYFBGIUFBOJW-UHFFFAOYSA-N

Isomeric SMILES

CN1C2=C(NC=N2)C(=O)N(C)C1=O

Average Molecular Weight

180.164

Monoisotopic Molecular Weight

180.06472552

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethylxanthine (CHEBI:28177 )
Purine alkaloids (C07130 )
a small molecule (CPD-12479 )

Ontology

Physiological effect

Health effect:

Health condition:

Nervous system disorders:

Seizure

Disposition

Route of exposure:

Enteral:

Ingestion

Naturally occurring process:

Biological process:

Biochemical pathway:

Asthma

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	-0.02	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 8.6 (25°)	DFC
Experimental Water Solubility	7.36 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Isoelectric point	Not Available
Mass Composition	C 46.67%; H 4.48%; N 31.10%; O 17.76%	DFC
Melting Point	Mp 264°	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)	splash10-00lr-9500000000-2c8464c2fe84464c207f	2014-09-20	View Spectrum
GC-MS	Theophylline, 1 TMS, GC-MS Spectrum	splash10-0f79-6970000000-224461ad62a44dbdf860	Spectrum
GC-MS	Theophylline, non-derivatized, GC-MS Spectrum	splash10-001j-7900000000-a08735d528e738752429	Spectrum
GC-MS	Theophylline, non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-d0882f7d959c726e7623	Spectrum
GC-MS	Theophylline, non-derivatized, GC-MS Spectrum	splash10-001i-9700000000-8d0e1898a6571fbca10a	Spectrum
GC-MS	Theophylline, non-derivatized, GC-MS Spectrum	splash10-0f79-6970000000-224461ad62a44dbdf860	Spectrum
Predicted GC-MS	Theophylline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fka-4900000000-878cab6882fd80efba3b	Spectrum
Predicted GC-MS	Theophylline, 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)	splash10-00di-0900000000-0092516012d6a2a93b31	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-4900000000-dcf52c18a6996f412b1a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-9000000000-09089337909892ef44cb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001j-7900000000-a08735d528e738752429	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CI-B (Unknown) , Positive	splash10-001i-0900000000-d0882f7d959c726e7623	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-c4943571126a44bb9e5a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-bc12ce29acd02fa749b8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03k9-0900000000-d63f60043f186fbb9bc0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-070l-4900000000-d293ab2fa6199dbaf97a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-05ru-9400000000-dde4775588d52c83806f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-556e382f583d610ef1f0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-89e34f5158856ba33469	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03k9-0900000000-65a6897d72954e875b00	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-070l-4900000000-df16604bd6c40cee8f24	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-05r3-9500000000-39a721dcecc86ed95507	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-1900000000-e67ff7ef9a955b90eb3f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-3900000000-1870952d98dbba22ace8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-7900000000-dc0e9606776c43a7823f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014j-9300000000-2c4c6490dda3ed3b563f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-26a6c0c23a465afdcde1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-01q9-1900000000-b11ca3441bb29fef1906	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-9400000000-63726fe0b49a9dc6ba7e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9100000000-139f765bc9b5855960c6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-88b5cb393b960973ac64	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00yi-9000000000-1ebbddce3c7133972546	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28177

Phenol-Explorer ID

Not Available

DrugBank ID

DB00277

HMDB ID

HMDB01889

CRC / DFC (Dictionary of Food Compounds) ID

BCK73-S:BCK73-S

EAFUS ID

Not Available

Dr. Duke ID

THEOPHYLLINE| DIMETHYLXANTHINE

BIGG ID

Not Available

KNApSAcK ID

C00001510

HET ID

TEP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Theophylline

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
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti apneic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bradyarrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cellulitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti emphysemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti neuralgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti rhinitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE