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

• ChemBase ID: 2903
• Molecular Formular: C14H6N2O8
• Molecular Mass: 330.20604
• Monoisotopic Mass: 330.01241516
• SMILES: OC(=O)c1cc(C(=O)O)c2c(n1)C(=O)C(=O)c1cc([nH]c21)C(=O)O
• Canonical SMILES: OC(=O)c1cc(nc2c1c1[nH]c(cc1C(=O)C2=O)C(=O)O)C(=O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• IUPAC Traditional name: pyrroloquinoline quinone
• Synonyms: 4,5-Dioxo-4,5-dihydro-1H-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid; Pyrroloquinoline Quinone; Methoxatin, Pyrroloquinoline, PQQ; 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic Acid; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

Database IDs

• CAS Number: 72909-34-3
• MDL Number: MFCD00043125
• PubChem SID: 160966350; 46505152
• PubChem CID: 1024
• CHEBI ID: 18315
• Chemspider ID: 997
• KEGG ID: C00113
• MeSH Name: PQQ+Cofactor
• Wikipedia Title: Pyrroloquinoline_quinone

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0483792
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -5.4917927
• LogD (pH = 7.4): -9.677663
• Log P: 0.36536938
• Molar Refractivity: 74.5325 cm^3
• Polarizability: 28.462883 Å^3
• Polar Surface Area: 174.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.46
• LOG S: -3.53
• Solubility (Water): 9.66e-02 g/l

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Orange-Red Solid
• Flash Point: 569.8 °C
• Density: 1.963 g/cm^3

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%; 97%; min 97%

DETAILS

DrugBank - DB03205

• Drug Groups: experimental
• Description: A pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES. [PubChem]

Toronto Research Chemicals - D449125

A cofactor of microbial quinoprotein enzyme, and imidazopyrroline. A redox/cofactor found in a a class of enzymes called quinoproteins.