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

Synonym	Source
1,3-Dimethyl-7H-purine-2,6-dione	ChEBI
1,3-Dimethylxanthine	ChEBI
Elixophyllin	ChEBI
Respbid	ChEBI
Theo-dur	ChEBI
Theolair	ChEBI
Theophyllin	ChEBI
Theophylline anhydrous	ChEBI
Uniphyl	ChEBI
Quibron-t	Kegg
Theo-24	Kegg
Theodur g	Kegg
Accurbron	HMDB
Acet-theocin	HMDB
Aerolate	HMDB
Aerolate III	HMDB
Aerolate SR	HMDB
Aminophylline	HMDB
Aquaphyllin	HMDB
Armophylline	HMDB
Asbron	HMDB
Asmax	HMDB
Austyn	HMDB
Bronkodyl	HMDB
Bronkodyl SR	HMDB
Choledyl sa	HMDB
Constant-T	HMDB
Diphyllin	HMDB
Doraphyllin	HMDB
Duraphyl	HMDB
Dyspne-inhal	HMDB
Elixex	HMDB
Elixicon	HMDB
Elixomin	HMDB
Elixophyllin SR	HMDB
Elixophylline	HMDB
Euphylline	HMDB
Euphylong	HMDB
Labid	HMDB
Lanophyllin	HMDB
Liquophylline	HMDB
Liquorice	HMDB
Maphylline	HMDB
Medaphyllin	HMDB
Nuelin	HMDB
Optiphyllin	HMDB
Parkophyllin	HMDB
Pseudotheophylline	HMDB
Quibron t/sr	HMDB
Quibron-t/sr	HMDB
Slo-bid	HMDB
Slo-phyllin	HMDB
Solosin	HMDB
Somophyllin-CRT	HMDB
Somophyllin-DF	HMDB
Somophyllin-T	HMDB
Spophyllin retard	HMDB
Sustaire	HMDB
Synophylate	HMDB
Synophylate-l.a. cenules	HMDB
T-Phyl	HMDB
Tefamin	HMDB
Teofilina	HMDB
Teofyllamin	HMDB
Teolair	HMDB
Theacitin	HMDB
Theal tabl.	HMDB
Theal tablets	HMDB
Theo-dur-sprinkle	HMDB
Theobid	HMDB
Theobid jr.	HMDB
Theochron	HMDB
Theocin	HMDB
Theoclair-SR	HMDB
Theoclear 80	HMDB
Theoclear l.a.-130	HMDB
Theoclear la	HMDB
Theoclear-200	HMDB
Theoclear-80	HMDB
Theocontin	HMDB
Theodel	HMDB
Theofol	HMDB
Theograd	HMDB
Theolair-SR	HMDB
Theolix	HMDB
Theolixir	HMDB
Theona p	HMDB
Theophyl	HMDB
Theophyl-225	HMDB
Theophyl-SR	HMDB
Theophyline	HMDB
Theophylline-SR	HMDB
Theostat 80	HMDB
Theovent	HMDB
Uni-dur	HMDB
Unifyl	HMDB
Uniphyllin	HMDB
Xanthium	HMDB
Xantivent	HMDB
Aerobin	HMDB
Bronchoparat	HMDB
Glycine theophyllinate	HMDB
Nuelin s.a.	HMDB
Slo phyllin	HMDB
SloPhyllin	HMDB
Somophyllin T	HMDB
Theo24	HMDB
Theoconfin continuous	HMDB
Theonite	HMDB
CT Arzneimittel brand OF theophylline sodium glycinate	HMDB
Von CT, theo	HMDB
Mundipharma brand OF theophylline sodium glycinate	HMDB
Quibron T SR	HMDB
Quibron T-SR	HMDB
Sodium glycinate, theophylline	HMDB
Theo 24	HMDB
Theophyllinate, glycine	HMDB
Theophylline sodium glycinate	HMDB
Theospan	HMDB
Uniphylline	HMDB
CT-Arzneimittel brand OF theophylline sodium glycinate	HMDB
ConstantT	HMDB
Fameasan brand OF theophylline sodium glycinate	HMDB
Lodrane	HMDB
Monospan	HMDB
Quibron TSR	HMDB
Theodur	HMDB
Theon	HMDB
Theopek	HMDB
Theostat	HMDB
CT, Theo von	HMDB
Theo von CT	HMDB
1,3 Dimethylxanthine	HMDB
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione	HMDB
Afonilum retard	HMDB
Anhydrous, theophylline	HMDB
Constant T	HMDB
Fujisawa brand OF theophylline sodium glycinate	HMDB
Glycinate, theophylline sodium	HMDB
SomophyllinT	HMDB
Theo dur	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
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, 9CI	db_source
Aerolate sr	HMDB
Bronkodyl sr	HMDB
Constant-t	HMDB
Elixophyllin sr	HMDB
Labophylline	biospider
Mudrane	biospider
Purine-2,6(1H,3H)-dione, 1,3-dimethyl-	biospider
Slophyllin	biospider
Somophyllin-crt	HMDB
Somophyllin-df	HMDB
Somophyllin-t	HMDB
T-phyl	HMDB
Teonova	db_source
Theoclair-sr	HMDB
Theokin	biospider
Theolair-sr	HMDB
Theona P	HMDB
Theophyl-sr	HMDB
Theophylline-sr	HMDB
Xanthine, 1,3-dimethyl-	biospider

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

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 46.67%; H 4.48%; N 31.10%; O 17.76%	DFC
Melting Point	Mp 264°	DFC
Boiling Point	Not Available
Experimental Water Solubility	7.36 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	-0.02	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 8.6 (25°)	DFC
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)	splash10-00lr-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

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
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	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-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 bradyarrhythmic	38070	An agent that increases heart rate, counteracting abnormally slow heart rhythms. It is used to treat bradyarrhythmias, such as atrioventricular block, and is commonly used in emergency medicine and cardiology to restore normal heart function.	DUKE
Anti-bronchitic	52217	An agent that relieves bronchial congestion and inflammation, commonly used in managing respiratory disorders such as bronchitis, asthma, and chronic obstructive pulmonary disease (COPD), to reduce coughing, wheezing, and shortness of breath.	DUKE
Anti cellulitic	52217	An agent that reduces the appearance of cellulite, improving skin texture and tone. It enhances blood flow, breaks down fat cells, and strengthens connective tissue, commonly used in cosmetic and dermatological treatments to minimize dimpling and orange peel skin.	DUKE
Antidote	50247	An agent that counteracts a poison or toxin, neutralizing its harmful effects. It plays a biological role in reversing toxicity, and has therapeutic applications in treating poisoning, overdose, and envenomation. Key medical uses include emergency treatment for snake bites, drug overdose, and chemical exposure.	DUKE
Anti emphysemic	52217	An agent that protects against emphysema, a lung disease. It helps maintain lung function, reduces inflammation, and prevents damage to alveoli. Therapeutically, anti-emphysemics are used to manage chronic obstructive pulmonary disease (COPD) and other respiratory disorders, improving breathing and overall lung health.	DUKE
Anti neuralgic	52217	An agent that relieves nerve pain, reducing inflammation and discomfort. It plays a biological role in blocking pain pathways, and has therapeutic applications in managing conditions like trigeminal neuralgia, shingles, and diabetic neuropathy. Key medical uses include treating severe nerve pain, numbness, and tingling sensations.	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-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	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
Arteriodilator		An agent that dilates arteries, increasing blood flow to or from the heart, used therapeutically to manage conditions like hypertension, heart failure, and angina, improving cardiac output and reducing blood pressure.	DUKE
Bronchodilator	35523	An agent that relaxes airway muscles, increasing airflow to the lungs. It reduces bronchospasm, commonly used in managing asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders to improve breathing and relieve symptoms.	DUKE
cAMP inhibitor	35222	An agent that blocks the activity of cyclic adenosine monophosphate (cAMP), a key signaling molecule. It reduces intracellular cAMP levels, modulating various biological processes. Therapeutically, cAMP inhibitors are used to treat conditions like asthma, cancer, and cardiovascular diseases by regulating cell signaling pathways and inflammation.	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
Cardiovascular	38070	A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.	DUKE
cGMP inhibitor	35222	An agent that blocks the activity of cyclic guanosine monophosphate (cGMP), reducing its signaling effects. It has therapeutic applications in treating conditions like priapism and pulmonary hypertension, and key medical uses include managing erectile dysfunction side effects and certain cardiovascular disorders.	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
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
Fetotoxic	52209	An agent that is toxic to the fetus, causing harm or developmental issues during pregnancy. Its biological role is to induce fetal damage, and it has no therapeutic applications. Key medical uses include serving as a warning or contraindication for certain medications or substances during pregnancy to prevent fetal harm.	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
Hyperuricemic		An agent that increases uric acid levels in the blood, playing a role in gout development. Therapeutically, it has limited applications, but is used in research to study gout and uric acid metabolism. Medically, it is used to induce gout-like conditions in clinical trials, aiding in the development of treatments for gout and other uric acid-related disorders.	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
Myocardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac function. It plays a biological role in increasing cardiac output and reducing symptoms of heart failure. Therapeutically, myocardiotonics are used to manage conditions like cardiomyopathy, heart failure, and coronary artery disease, improving overall cardiac performance.	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
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
Prostaglandin secretor		An agent that stimulates the release of prostaglandins, reducing gastric acid secretion and protecting the gastrointestinal mucosa. Therapeutically, it is used to prevent NSAID-induced ulcers and gastroesophageal reflux disease (GERD), and to manage conditions like Zollinger-Ellison syndrome.	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
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

Enzymes

Name	Gene Name	UniProt ID
Adenosine deaminase	ADA	P00813
Adenosine receptor A1	ADORA1	P30542
Adenosine receptor A2a	ADORA2A	P29274
Adenosine receptor A2b	ADORA2B	P29275

Pathways

Name	SMPDB Link	KEGG Link
Caffeine Metabolism	SMP00028	map00232

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— 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.