(2S,3S)-2,3-bis(2H-1,3-benzodioxol-5-ylmethyl)butanedioic acid

• ChemBase ID: 1912
• Molecular Formular: C20H18O8
• Molecular Mass: 386.35212
• Monoisotopic Mass: 386.10016754
• SMILES: [C@H](C(=O)O)(Cc1ccc2OCOc2c1)[C@@H](C(=O)O)Cc1ccc2OCOc2c1
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)Cc1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
• InChI: InChI=1S/C20H18O8/c21-19(22)13(5-11-1-3-15-17(7-11)27-9-25-15)14(20(23)24)6-12-2-4-16-18(8-12)28-10-26-16/h1-4,7-8,13-14H,5-6,9-10H2,(H,21,22)(H,23,24)/t13-,14-/m0/s1
• InChIKey: FFYBYVPVYLMLAR-KBPBESRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(2H-1,3-benzodioxol-5-ylmethyl)butanedioic acid
• IUPAC Traditional name: (2S,3S)-2,3-bis(2H-1,3-benzodioxol-5-ylmethyl)butanedioic acid
• Synonyms: 2,3-Bis-Benzo[1,3]Dioxol-5-Ylmethyl-Succinic Acid

Database IDs

• PubChem SID: 46508008; 160965367
• PubChem CID: 5496628

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2392187
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.38208276
• LogD (pH = 7.4): -2.524571
• Log P: 3.0907018
• Molar Refractivity: 93.6118 cm^3
• Polarizability: 37.054573 Å^3
• Polar Surface Area: 111.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.96
• LOG S: -3.52
• Solubility (Water): 1.17e-01 g/l

DETAILS

DrugBank - DB02154

Drug information: experimental