pyrroloquinoline quinone (CHEBI:18315)

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ChEBI Name	pyrroloquinoline quinone

ChEBI ID	CHEBI:18315

Definition	A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.

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

Secondary ChEBI IDs	CHEBI:45251, CHEBI:49082, CHEBI:7881, CHEBI:14986, CHEBI:26460

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Formula

C14H6N2O8

Net Charge

Average Mass

330.20612

Monoisotopic Mass

330.01242

InChI

InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)

InChIKey

MMXZSJMASHPLLR-UHFFFAOYSA-N

SMILES

OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c1cc([nH]c-21)C(O)=O

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). (via pyrroloquinoline cofactor ) water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	pyrroloquinoline quinone (CHEBI:18315) has role anti-inflammatory agent (CHEBI:67079) pyrroloquinoline quinone (CHEBI:18315) has role antioxidant (CHEBI:22586) pyrroloquinoline quinone (CHEBI:18315) has role cofactor (CHEBI:23357) pyrroloquinoline quinone (CHEBI:18315) has role water-soluble vitamin (role) (CHEBI:27314) pyrroloquinoline quinone (CHEBI:18315) is a orthoquinones (CHEBI:25622) pyrroloquinoline quinone (CHEBI:18315) is a pyrroloquinoline cofactor (CHEBI:26461) pyrroloquinoline quinone (CHEBI:18315) is a tricarboxylic acid (CHEBI:27093) pyrroloquinoline quinone (CHEBI:18315) is conjugate acid of pyrroloquinoline quinone(3−) (CHEBI:58442)

Incoming	pyrroloquinoline quinone(3−) (CHEBI:58442) is conjugate base of pyrroloquinoline quinone (CHEBI:18315)

IUPAC Name

4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

Synonyms	Sources
2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone	RESID
2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione	ChemIDplus
4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid	RESID
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate	KEGG COMPOUND
coenzyme PQQ	ChemIDplus
Methoxatin	KEGG COMPOUND
methoxatin	ChemIDplus
PQQ	KEGG COMPOUND
Pyrrolo-quinoline quinone	KEGG COMPOUND
Pyrroloquinoline quinone	KEGG COMPOUND
PYRROLOQUINOLINE QUINONE	PDBeChem
Pyrroloquinoline-quinone	KEGG COMPOUND

Last Modified

04 August 2021