theophylline (CHEBI:28177)

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CHEBI:28177 - theophylline

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ChEBI Name	theophylline

ChEBI ID	CHEBI:28177

Definition	A dimethylxanthine having the two methyl groups located at positions 1 and 3. It is structurally similar to caffeine and is found in green and black tea.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45950, CHEBI:9523, CHEBI:26940

Supplier Information	ChemicalBook:CB6441658, eMolecules:530918

Download	Molfile XML SDF

more structures >>

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21 22 0 0 0 0 999 V2000

-0.5094 1.0221 -0.2901 C 0 0 0 0 0 0 0 0 0 4 0 0

0.8524 1.0753 -0.0029 C 0 0 0 0 0 0 0 0 0 5 0 0

-1.2050 -0.1303 -0.2203 N 0 0 0 0 0 0 0 0 0 3 0 0

0.7885 -1.2529 0.4074 N 0 0 0 0 0 0 0 0 0 1 0 0

-0.5405 -1.2437 0.1419 C 0 0 0 0 0 0 0 0 0 2 0 0

1.4808 -0.1041 0.3577 C 0 0 0 0 0 0 0 0 0 6 0 0

1.2586 2.3438 -0.1560 N 0 0 0 0 0 0 0 0 0 7 0 0

-0.8915 2.2719 -0.6131 N 0 0 0 0 0 0 0 0 0 9 0 0

0.1892 3.0626 -0.5280 C 0 0 0 0 0 0 0 0 0 8 0 0

-1.1827 -2.2883 0.2330 O 0 0 0 0 0 0 0 0 0 0 0 0

2.6737 0.0093 0.6130 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.5868 -0.1181 -0.5297 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4416 -2.4766 0.7280 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1569 2.6852 -0.0249 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1866 4.0649 -0.7209 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1677 -0.4502 0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7886 -0.7890 -1.3676 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0072 0.8496 -0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0036 -2.9212 1.6254 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3323 -3.1904 -0.0928 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5153 -2.4200 0.9231 H 0 0 0 0 0 0 0 0 0 0 0 0

8 1 4 0 0 0 0

2 1 4 0 0 0 0

7 2 4 0 0 0 0

3 1 1 0 0 0 0

5 4 1 0 0 0 0

5 3 1 0 0 0 0

10 5 2 0 0 0 0

6 2 1 0 0 0 0

6 4 1 0 0 0 0

11 6 2 0 0 0 0

9 7 4 0 0 0 0

9 8 4 0 0 0 0

14 7 1 0 0 0 0

9 15 1 0 0 0 0

12 3 1 0 0 0 0

13 4 1 0 0 0 0

12 16 1 0 0 0 0

12 17 1 0 0 0 0

12 18 1 0 0 0 0

13 19 1 0 0 0 0

13 20 1 0 0 0 0

13 21 1 0 0 0 0

M APO 2 12 1 13 1

M STY 2 1 SUP 2 SUP

M SAL 1 4 12 16 17 18

M SBL 1 1 15

M SMT 1 Me

M SDS EXP 1 1

M SAL 2 4 13 19 20 21

M SBL 2 1 16

M SMT 2 Me

M SDS EXP 1 2

M END): 20 ms

reading 21 atoms

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21 atoms created

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Wikipedia	License
Theophylline, also known as 1,3-dimethylxanthine, is a drug that inhibits phosphodiesterase and blocks adenosine receptors. It is used to treat chronic obstructive pulmonary disease (COPD) and asthma. Its pharmacology is similar to other methylxanthine drugs (e.g., theobromine and caffeine). Trace amounts of theophylline are naturally present in tea, coffee, chocolate, yerba maté, guarana, and kola nut. The name 'theophylline' derives from "Thea"—the former genus name for tea + Legacy Greek φύλλον (phúllon, "leaf") + -ine.
Read full article at Wikipedia

Formula

C7H8N4O2

Net Charge

Average Mass

180.16418

Monoisotopic Mass

180.06473

InChI

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

InChIKey

ZFXYFBGIUFBOJW-UHFFFAOYSA-N

SMILES

Cn1c2nc[nH]c2c(=O)n(C)c1=O

Metabolite of Species	Details
Citrus limon (NCBI:txid2708)	See: DOI
Citrus maxima (NCBI:txid37334)	See: DOI
Citrus x paradisi (NCBI:txid37656)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in blood serum (BTO:0000133). See: MetaboLights Study

Roles Classification
Biological Role(s):	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*). immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. adenosine receptor antagonist An antagonist at any adenosine receptor. drug metabolite fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	muscle relaxant A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis. bronchodilator agent An agent that causes an increase in the expansion of a bronchus or bronchial tubes. vasodilator agent A drug used to cause dilation of the blood vessels. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. anti-inflammatory agent Any compound that has anti-inflammatory effects. anti-asthmatic drug A drug used to treat asthma.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	theophylline (CHEBI:28177) has role adenosine receptor antagonist (CHEBI:71232) theophylline (CHEBI:28177) has role anti-asthmatic drug (CHEBI:49167) theophylline (CHEBI:28177) has role anti-inflammatory agent (CHEBI:67079) theophylline (CHEBI:28177) has role bronchodilator agent (CHEBI:35523) theophylline (CHEBI:28177) has role drug metabolite (CHEBI:49103) theophylline (CHEBI:28177) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218) theophylline (CHEBI:28177) has role fungal metabolite (CHEBI:76946) theophylline (CHEBI:28177) has role human blood serum metabolite (CHEBI:85234) theophylline (CHEBI:28177) has role immunomodulator (CHEBI:50846) theophylline (CHEBI:28177) has role muscle relaxant (CHEBI:51371) theophylline (CHEBI:28177) has role vasodilator agent (CHEBI:35620) theophylline (CHEBI:28177) is a dimethylxanthine (CHEBI:23818)

Incoming	aminophylline (CHEBI:2659) has part theophylline (CHEBI:28177)

IUPAC Name

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

Synonyms	Sources
1,3-dimethyl-7H-purine-2,6-dione	IUPHAR
1,3-Dimethylxanthine	KEGG COMPOUND
Theophyllin	ChemIDplus
Theophylline	KEGG COMPOUND
THEOPHYLLINE	PDBeChem
theophylline	UniProt
théophylline	ChEBI
theophylline anhydrous	ChemIDplus

Brand Names	Sources
Elixophyllin	KEGG DRUG
Respbid	ChemIDplus
Theo-Dur	ChemIDplus
Theolair	KEGG DRUG
Uniphyl	KEGG DRUG

Manual Xrefs	Databases
1801	VSDB
2620	DrugCentral
C00001510	KNApSAcK
C07130	KEGG COMPOUND
CPD-12479	MetaCyc
D00371	KEGG DRUG
DB00277	DrugBank
HMDB0001889	HMDB
TEP	PDBeChem
Theophylline	Wikipedia
View more database links

Registry Numbers	Types	Sources
13463	Reaxys Registry Number	Reaxys
51226	Gmelin Registry Number	Gmelin
58-55-9	CAS Registry Number	KEGG COMPOUND
58-55-9	CAS Registry Number	NIST Chemistry WebBook
58-55-9	CAS Registry Number	ChemIDplus

Citations

Last Modified

22 February 2017

CHEBI:28177 - theophylline

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