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Term:
pyrroloquinoline quinone (CHEBI:18315)
Annotations: Rat: (37) Mouse: (38) Human: (37) Chinchilla: (0) Bonobo: (0) Dog: (0) Squirrel: (0) Pig: (0)
Parent Terms Term With Siblings Child Terms
cofactor +   
orthoquinones +     
tricarboxylic acid +     
(-)-threo-isodihomocitric acid 
(13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid 
(1E)-4-oxobut-1-ene-1,2,4-tricarboxylic acid 
(1R,2S,5S,6S)-2-(3-carboxypropanoyl)-5-[(1-carboxyvinyl)oxy]-6-hydroxycyclohex-3-ene-1-carboxylic acid 
(2E)-but-2-ene-1,2,3-tricarboxylic acid 
(2R)-dihomocitric acid 
(2R)-trihomocitric acid 
(2R,3E)-5-oxopent-3-ene-1,2,5-tricarboxylic acid 
(2S,3S)-2-hydroxytridecane-1,2,3-tricarboxylic acid 
(2Z)-4-oxobut-2-ene-1,2,4-tricarboxylic acid 
(2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid 
(3S,4S)-3-hydroxytetradecane-1,3,4-tricarboxylic acid 
(6R)-5,10-methylenetetrahydrofolate(2-) +  
(6R)-5,10-methylenetetrahydrofolic acid +  
(6S)-5,6,7,8-tetrahydrofolate(2-) 
(6S)-5,6,7,8-tetrahydrofolic acid 
(8S)-glutathionyl-(7R,17S)-dihydroxy-(4Z,9,11,13Z,15E,19Z)-docosahexaenoic acid 
(carboxymethoxy)succinic acid 
(R)-carnitine +   
(R)-lipoate 
(R)-lipoic acid +   
(Z)-but-2-ene-1,2,3-tricarboxylic acid 
(Z)-N(6)-[(4R,5S)-5-(2-carboxyethyl)-4-(carboxymethyl)piperidin-3-ylidene]-L-lysine 
1,1,1-propanetricarboxylic acid 
1,2-benzoquinones +   
1,2-naphthoquinones +   
1,4-benzoquinone +   
11,12-dihydro-(12R)-hydroxyleukotriene C4 
11,12-dihydro-12-oxoleukotriene C4 
12-demethylmultiorthoquinone 
16(S)-glutathionyl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid 
16-carboxy-17,18,19,20-tetranor-leukotriene E3 
16-carboxy-Delta(13)-17,18,19,20-tetranor-leukotriene E4 +  
18-carboxy-19,20-dinor-leukotriene E4 
2'-deoxymugineic acid 
2,5-S,S'-dicysteinyldopa 
2-caffeoylisocitric acid 
2-carboxy-cis,cis-muconic acid 
2-hydroxy-4-oxobutane-1,2,4-tricarboxylic acid +  
2-hydroxy-5-carboxymethylmuconic acid 
2-methylcitric acid +  
2-oxaloglutaric acid 
20-carboxyleukotriene E4 
3'-hydroxyechinenone 
3-(2-carboxyethenyl)-cis,cis-muconic acid 
3-bromo-beta-lapachone 
3-carboxy-cis,cis-muconic acid 
3-carboxymethylmuconic acid 
3-epi-3-hydroxymugineic acid 
3-hydroxybutane-1,2,3-tricarboxylic acid +  
3-hydroxytetradecane-1,3-4-tricarboxylic acid 
3-oxalomalic acid  
4-carboxy-2-hydroxyhexa-2,4-dienedioic acid +  
5,6,7,8-tetrahydropteridine 
5-hydroxybenzimidazolylcob(I)amide 
5-hydroxybenzimidazolylcob(I)amide(1-) 
5-hydroxypenta-2,4-diene-1,2,5-tricarboxylic acid +  
5-oxopent-3-ene-1,2,5-tricarboxylic acid +  
6,7-dimethyl-8-(1-D-ribityl)lumazine 
6,7-dimethyl-8-(1-D-ribityl)lumazine(1-) 
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylic acid 
6-decylubiquinone  
6-hydroxy-FAD 
6-hydroxy-FAD(3-) 
\{(2S,3S,4S)-2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methylhexa-1,3-dienyl]pyrrolidin-3-yl\}acetic acid 
acenaphthoquinone  
aconitic acid +   
acromelic acid A 
adenosine 5'-monophosphate +   
adenosine 5'-monophosphate(2-) +  
ammonium +   
anthranilic acid +   
ATP +   
ATP(3-) 
ATP(4-) +  
aurintricarboxylic acid  
avenic acid A +  
B vitamin +   
bacillithiol 
barium(2+) 
benzene-1,3,5-tricarboxylic acid +  
benzo[a]pyrene-7,8-dione  
beta-carotene +   
beta-lapachone  
betanidin quinone 
biotin +   
biotinate +  
bis(molybdopterin)tungsten cofactor 
bongkrekic acid  
but-1-ene-1,2,4-tricarboxylic acid +  
cadmium(2+) +   
calcium(2+) +   
Carbamazepine-o-quinone 
cerium(3+) 
chloride +   
chlorophyll a +  
chlorophyll a(1-) +  
chlorophyll b 
chlorophyll b(1-) 
cis-dihomoaconitic acid 
cis-trihomoaconitic acid 
citric acid +   
citric acid-d4 
cob(I)alamin 
cob(I)alamin(1-) 
cob(II)alamin 
cobalamin +  
cobalt(2+) +   
cobalt(3+) 
cobamamide +   
coenzyme +   
coenzyme F430 
coenzyme F430(5-) 
copper cation +   
copper(1+) +   
copper(2+) +   
corrin 
corrinoid +   
cysteine tryptophylquinone +  
D-nopaline 
decylplastoquinone 
dehydro-D-arabinono-1,4-lactone 
dibenzo[1,4]dioxine-2,3-dione 
dihydrogenvanadate 
dihydrolipoamide +   
dipyrromethane cofactor 
dipyrromethane cofactor(4-) 
divinyl chlorophyll a 
divinyl chlorophyll a(1-) 
divinyl chlorophyll b 
divinyl chlorophyll b(1-) 
domoic acid  
dopachrome +   
echinenone +  
estra-1(10),4-diene-2,3,17-trione 
estra-1,5(10)-diene-3,4,17-trione 
ethylenediaminetriacetic acid 
FAD  
FAD(3-) 
Fe-coproporphyrin III 
Fe-coproporphyrin III(4-) 
Fe4S2O2 iron-sulfur-oxygen cluster 
ferriheme a 
ferriheme a(1-) 
ferroheme b +   
ferroheme b(2-) 
ferroheme c 
ferroheme c(2-) 
flavin adenine dinucleotide +   
flavin mononucleotide +   
FluoZin-3 
FMN +   
FMN(3-) +  
FMNH2 +  
FMNH2(2-) 
gamma-carboxy-L-glutamic acid +  
gamma-D-glutamyl-meso-diaminopimelic acid 
gibberellin A13 
gibberellin A17 
gibberellin A25 
gibberellin A28 
glutathionate(1-) +  
glutathione +   
glycyrrhizinic acid  
H3HP-DO3A +  
heme d cis-diol +  
heme d cis-diol(2-) 
heme o +  
homocitric acid +  
homoisocitric acid +  
hydrogen peroxide +   
hydrogencarbonate +   
hydrogenphosphate +  
hydroquinone +   
indole-5,6-quinone 
iron cation +   
iron(2+) +   
iron(3+) +   
iron-sulfur-iron cofactor 
iron-sulfur-molybdenum cofactor 
iron-sulfur-vanadium cofactor 
isocitric acid +  
L-2-succinylamino-6-oxoheptanedioic acid 
L-ascorbate +  
L-ascorbic acid +   
L-beta-carboxyaspartic acid 
L-gamma-carboxyglutamic acid 
laccaic acid C +  
laccaridione A 
laccaridione B 
lanthanum(3+) 
lead(2+) +   
magnesium(2+) +  
manganese(2+) +   
methylcobalamin  
methylisocitric acid +  
molybdopterin cofactor +  
mugineic acids +  
multiorthoquinone 
mycothiol +  
myo-inositol hexakisphosphate  
myo-inositol hexakisphosphate(12-) 
N(2)-succinyl-L-glutamic acid 
N-[(2S)-2-amino-2-carboxyethyl]-L-glutamic acid 
N-acetyl-S-(2-succino)-L-cysteine 
N-succinyl-LL-2,6-diaminopimelic acid 
NAD(+)  
NAD(1-) +  
NADH +  
NADH(2-) +  
NADP(+) +   
NADP(3-) 
NADPH +  
NADPH(4-) +  
Ni(II)-pyridinium-3,5-bisthiocarboxylate mononucleotide(1-) 
Ni(II)-pyridinium-3,5-bisthiocarboxylic acid mononucleotide 
nickel cation +   
nickel(2+) +   
nicotinamide +   
NiFe4S4 cluster 
nitrilotriacetic acid +  
nocardione A 
ornaline 
oxalosuccinic acid +  
pantetheine 4'-phosphate +  
pantetheine 4'-phosphate(2-) +  
pantothenic acids +   
phanquone 
phylloquinone +   
phytochromobilin +  
polypeptide-derived cofactor +  
porphyrins +   
potassium(1+) +   
premycofactocin +  
prenyl-FMN 
prenyl-FMN(2-) 
prenyl-FMNH2 
prosthetic group +   
pyridoxal +   
pyridoxal 5'-phosphate +   
pyridoxal 5'-phosphate(2-) 
pyridoxal hydrochloride 
pyridoxine +   
pyrroloquinoline cofactor +   
pyrroloquinoline quinol 
pyrroloquinoline quinone  
A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.
pyrroloquinoline quinone(3-) 
pyrroloquinoline semiquinone 
pyruvate +  
pyruvic acid +   
riboflavin +   
riboflavin(1-) 
S-(2-succinyl)-L-cysteine 
S-adenosyl-L-homocysteine  
S-adenosyl-L-methionine +   
S-adenosyl-L-methionine zwitterion +  
sapropterin +   
siderophore +   
siroheme 
siroheme(8-) 
sirohydrochlorin +  
sirohydrochlorin(8-) 
sodium ascorbate 
sodium(1+) +   
staphyloferrin B 
strontium(2+) 
sulfate +   
TCEP  
tetra-mu3-sulfido-tetrairon +  
tetrahydromonapterin 
thiamine(1+) +   
thiamine(1+) diphosphate +  
thiamine(1+) diphosphate(3-) 
trachyspic acid 
tricarballylic acid +   
trimellitic acid +   
vanadium cation +  
vibrioferrin 
vitamin B6 phosphate +   
vitamin C +   
zaragozic acid A +   
zaragozic acid C 
zeaxanthin +  
zinc(2+) +   

Synonyms
Exact Synonyms: 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
Related Synonyms: 2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone ;   2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione ;   4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate ;   4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid ;   Formula=C14H6N2O8 ;   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 ;   PQQ ;   Pyrrolo-quinoline quinone ;   SMILES=OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c1cc([nH]c-21)C(O)=O ;   coenzyme PQQ ;   methoxatin
Alternate IDs: CHEBI:14986 ;   CHEBI:26460 ;   CHEBI:45251 ;   CHEBI:49082 ;   CHEBI:7881
Xrefs: Beilstein:3596812 ;   CAS:72909-34-3 ;   COMe:MOL000073 ;   DrugBank:DB03205 ;   Gmelin:56633 ;   KEGG:C00113
Xref Mesh: MESH:D045542
Xrefs: PDBeChem:PQQ ;   RESID:AA0283
Cyclic Relationships: is_conjugate_acid_of CHEBI:58442

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.