(4R,5R,6R)-pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,7,9,11,13,15,17,19-octaene-4,5,6-triol

• ChemBase ID: 5083
• Molecular Formular: C20H16O3
• Molecular Mass: 304.33924
• Monoisotopic Mass: 304.10994437
• SMILES: c1ccc2ccc3c4c(cc5ccc1c2c35)[C@@H](O)[C@H](O)[C@H](O)C4
• Canonical SMILES: O[C@@H]1Cc2c([C@H]([C@@H]1O)O)cc1c3c2ccc2c3c(cc1)ccc2
• InChI: InChI=1S/C20H16O3/c21-16-9-14-13-7-6-11-3-1-2-10-4-5-12(18(13)17(10)11)8-15(14)19(22)20(16)23/h1-8,16,19-23H,9H2/t16-,19-,20-/m1/s1
• InChIKey: GFANZDFKCCJYRF-NSISKUIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5R,6R)-pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,7,9,11,13,15,17,19-octaene-4,5,6-triol
• IUPAC Traditional name: (4R,5R,6R)-pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,7,9,11,13,15,17,19-octaene-4,5,6-triol
• Synonyms: 1,2,3-TRIHYDROXY-1,2,3,4-TETRAHYDROBENZO[A]PYRENE

Database IDs

• PubChem SID: 99443906; 160968514
• PubChem CID: 5287739

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.865665
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.3555634
• LogD (pH = 7.4): 2.355562
• Log P: 2.3555634
• Molar Refractivity: 88.4433 cm^3
• Polarizability: 37.96709 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.43
• LOG S: -4.14
• Solubility (Water): 2.18e-02 g/l

DETAILS

DrugBank - DB07435

Drug information: experimental