Pyrroloquinoline Quinone

Details

• Internal ID: aa8a8326-1608-4cb8-a64b-61f2bf773592
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Pyrroloquinolines > Pyrroloquinoline quinones
• IUPAC Name: 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• 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)
• InChI Key: MMXZSJMASHPLLR-UHFFFAOYSA-N
• Popularity: 1,862 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₆N₂O₈
• Molecular Weight: 330.21 g/mol
• Exact Mass: 330.01241515 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 72909-34-3
• methoxatin
• Coenzyme pqq
• Pyrrolo-quinoline quinone
• Pqq coenzyme
• Pqq cofactor
• 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• 2,7,9-Tricarboxypyrroloquinoline quinone
• DTXSID3041162
• CHEBI:18315
• 47819QGH5L
• pyrroloquinolinedione tricarboxylic acid
• 2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione
• 1H-Pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
• Coenzyme, PQQ
• Cofactor, PQQ
• PQQ, Coenzyme
• Quinone, Pyrroloquinoline
• Pyrrolo Quinoline Quinone
• Quinone, Pyrrolo-Quinoline
• 2,4,6-tricarboxylic-pyrrolo(2,3-5,6)quinoline 8,9-quinone
• 2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone
• 4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
• 4,5-dioxo-1H,4H,5H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
• 1H-Pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
• 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-5,6)quinoline-2,7,9-tricarboxylic acid
• 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid
• RefChem:871130
• 4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
• DTXCID1021162
• 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-tricarboxylic acid
• Methoxatine
• PQQ
• MFCD00043125
• Pyrroloquinoline-quinone
• PQQ;Methoxatin
• C14H6N2O8
• 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• 4,5-Dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
• UNII-47819QGH5L
• Methoxantin
• Pyroquinoline Quinone
• Pyrroloquinoline dione
• Pyrroloquinolinequinone(PQQ)
• SCHEMBL37975
• orb1301578
• orb3025137
• Pyrroloquinoline Quinone (PQQ)
• CHEMBL1235421
• SCHEMBL21049248
• SCHEMBL29350225
• GLXC-26180
• BDBM50575553
• MSK158015
• AKOS015920260
• CS-W009276
• DB03205
• EBC-616001
• FD21985
• GS-6613
• MSK158015-100W
• Pyrroloquinoline dione tricarboxylic acid
• MSK158015-1000W
• PYRROLOQUINOLINE QUINONE [WHO-DD]
• PYRROLOQUINOLINEDIONE TRICARBOXYLATE
• SY025685
• DB-055694
• HY-100196
• NS00068569
• P2781
• Pyrroloquinoline quinone, >=95.0% (HPLC)
• C00113
• F079870
• Q414583
• Pyrroloquinoline quinone Solution in Water, 1000ug/mL
• Pyrroloquinoline quinone Solution in Water, 100ug/mL
• 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylicacid
• 2,7,9-TRICARBOXY-4,5-DIHYDRO-4,5-DIOXO-1H-PYRROLO(2,3-F)QUINOLINE
• 4,5-Dioxo-4,5-dihydro-1H-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8843	88.43%
Caco-2	-	0.8695	86.95%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7655	76.55%
OATP2B1 inhibitior	-	0.7020	70.20%
OATP1B1 inhibitior	+	0.9379	93.79%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8811	88.11%
P-glycoprotein inhibitior	-	0.9495	94.95%
P-glycoprotein substrate	-	0.8801	88.01%
CYP3A4 substrate	-	0.6197	61.97%
CYP2C9 substrate	-	0.7786	77.86%
CYP2D6 substrate	-	0.9039	90.39%
CYP3A4 inhibition	-	0.9038	90.38%
CYP2C9 inhibition	-	0.7198	71.98%
CYP2C19 inhibition	-	0.7513	75.13%
CYP2D6 inhibition	-	0.8200	82.00%
CYP1A2 inhibition	+	0.7860	78.60%
CYP2C8 inhibition	-	0.7738	77.38%
CYP inhibitory promiscuity	-	0.8592	85.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9230	92.30%
Carcinogenicity (trinary)	Non-required	0.7024	70.24%
Eye corrosion	-	0.9950	99.50%
Eye irritation	+	0.7599	75.99%
Skin irritation	-	0.7960	79.60%
Skin corrosion	-	0.9663	96.63%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9161	91.61%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.9101	91.01%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6711	67.11%
Acute Oral Toxicity (c)	III	0.4348	43.48%
Estrogen receptor binding	-	0.6106	61.06%
Androgen receptor binding	+	0.6100	61.00%
Thyroid receptor binding	-	0.7778	77.78%
Glucocorticoid receptor binding	+	0.6230	62.30%
Aromatase binding	+	0.5677	56.77%
PPAR gamma	+	0.5182	51.82%
Honey bee toxicity	-	0.9497	94.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.7143	71.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1811	P34995	Prostanoid EP1 receptor	95.86%	95.71%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	94.43%	95.72%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	92.92%	81.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	92.43%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.08%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	88.06%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.76%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.24%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.14%	96.67%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.50%	96.38%
CHEMBL2047	Q96RI1	Bile acid receptor FXR	85.30%	96.10%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.86%	93.03%
CHEMBL1881	P43116	Prostanoid EP2 receptor	81.56%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.15%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 1024
• LOTUS: LTS0120678
• wikiData: Q414583