pyrroloquinoline quinone (CHEBI:18315)

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CHEBI:18315 - pyrroloquinoline quinone

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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

Supplier Information	ChemicalBook:CB3674978, eMolecules:494174, ZINC000003861770

Download	Molfile XML SDF

more structures >>

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30 32 0 0 0 0 999 V2000

-0.0420 -1.7672 -0.2868 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2466 -2.2571 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3258 -1.4103 -0.6270 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2899 -0.3735 -0.0969 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8667 0.4623 -0.1329 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1435 -0.0534 -0.3868 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0145 1.7801 0.0641 N 0 0 0 0 0 0 0 0 0 0 0 0

2.2972 2.1625 -0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0369 1.0165 -0.3267 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0886 -2.6284 -0.1849 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.3796 -2.2826 0.0577 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6601 -0.9049 0.1699 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6321 0.0642 0.0994 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7161 3.4610 0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8872 3.7930 0.0435 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9203 4.3403 0.4570 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3452 -3.2678 0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.5164 -3.0205 0.4459 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0804 -4.4586 0.0839 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0322 1.3839 0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8818 1.8702 -0.4948 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.6042 2.1030 1.1304 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4523 -1.8194 -0.8836 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4061 -3.4536 -0.7794 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2954 2.3948 0.2598 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0488 0.9673 -0.4669 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6315 -0.6112 0.3216 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1207 4.6336 0.1706 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7155 -5.0620 0.1773 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8784 2.9379 1.1934 H 0 0 0 0 0 0 0 0 0 0 0 0

1 10 4 0 0 0 0

2 1 1 0 0 0 0

24 2 2 0 0 0 0

3 2 1 0 0 0 0

23 3 2 0 0 0 0

4 1 4 0 0 0 0

13 4 4 0 0 0 0

5 4 1 0 0 0 0

7 5 4 0 0 0 0

6 5 4 0 0 0 0

3 6 1 0 0 0 0

9 6 4 0 0 0 0

8 7 4 0 0 0 0

9 8 4 0 0 0 0

14 8 1 0 0 0 0

11 10 4 0 0 0 0

12 11 4 0 0 0 0

17 11 1 0 0 0 0

12 13 4 0 0 0 0

20 13 1 0 0 0 0

15 14 1 0 0 0 0

16 14 2 0 0 0 0

18 17 2 0 0 0 0

19 17 1 0 0 0 0

21 20 2 0 0 0 0

22 20 1 0 0 0 0

7 25 1 0 0 0 0

9 26 1 0 0 0 0

12 27 1 0 0 0 0

15 28 1 0 0 0 0

19 29 1 0 0 0 0

22 30 1 0 0 0 0

M END): 20 ms

reading 30 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

30 atoms created

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Wikipedia	License
Creatine ( or ) is an organic compound with the nominal formula (H2N)(HN)CN(CH3)CH2CO2H. It exists in various tautomers in solutions (among which are neutral form and various zwitterionic forms). Creatine is found in vertebrates, where it facilitates recycling of adenosine triphosphate (ATP), primarily in muscle and brain tissue. Recycling is achieved by converting adenosine diphosphate (ADP) back to ATP via donation of phosphate groups. Creatine also acts as a buffer.
Read full article at Wikipedia

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.

View more via ChEBI Ontology

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

Manual Xrefs	Databases
997	ChemSpider
AA0283	RESID
C00053736	KNApSAcK
C00113	KEGG COMPOUND
DB03205	DrugBank
FDB012848	FooDB
HMDB0013636	HMDB
MOL000073	COMe
PQQ	PDBeChem
Pyrroloquinoline_quinone	Wikipedia
View more database links

Registry Numbers	Types	Sources
3596812	Beilstein Registry Number	Beilstein
56633	Gmelin Registry Number	Gmelin
72909-34-3	CAS Registry Number	ChemIDplus

Citations

Last Modified

04 August 2021

CHEBI:18315 - pyrroloquinoline quinone

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