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:CB9733804, eMolecules:535136, Selleckchem:bay-11-7082-bay-11-7821, ZINC000002568458

Download	Molfile XML SDF

more structures >>

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Marvin 02060823343D

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
Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken orally (swallowed by mouth), or less commonly by either intramuscular injection or by an IV bolus injection, which is a relatively quick intravenous injection lasting from a couple of seconds to a few minutes. Common adverse effects include nausea and rash. It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not be used in those who are allergic to penicillin. While usable in those with kidney problems, the dose may need to be decreased. Its use in pregnancy and breastfeeding does not appear to be harmful. Amoxicillin is in the β-lactam family of antibiotics. Amoxicillin was discovered in 1958 and came into medical use in 1972. Amoxil was approved for medical use in the United States in 1974, and in the United Kingdom in 1977. It is on the World Health Organization's List of Essential Medicines. It is one of the most commonly prescribed antibiotics in children. Amoxicillin is available as a generic medication. In 2022, it was the 26th most commonly prescribed medication in the United States, with more than 20 million prescriptions.
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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