(1R,4R,7R,9R,10R,13R,15S)-7-{[(2S,3R,4R,5S,6S)-6-(hydroperoxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5,5-dicarboxylic acid

• ChemBase ID: 2164
• Molecular Formular: C31H46O19S2
• Molecular Mass: 786.81554
• Monoisotopic Mass: 786.20747125
• SMILES: CC(C)CC(=O)O[C@H]1[C@@H](O[C@@H]2C[C@]3(C)[C@H]4CC[C@H]5C[C@@]4(CC[C@H]3C(C2)(C(=O)O)C(=O)O)[C@@H](O)C5=C)O[C@@H](COO)[C@H](OS(=O)(=O)O)[C@@H]1OS(=O)(=O)O
• Canonical SMILES: OOC[C@@H]1O[C@H](O[C@H]2CC(C(=O)O)(C(=O)O)[C@H]3[C@@](C2)(C)[C@H]2CC[C@H]4C[C@@]2(CC3)[C@@H](O)C4=C)[C@@H]([C@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)OC(=O)CC(C)C
• InChI: InChI=1S/C31H46O19S2/c1-14(2)9-21(32)48-24-23(50-52(42,43)44)22(49-51(39,40)41)18(13-45-38)47-26(24)46-17-11-29(4)19-6-5-16-10-30(19,25(33)15(16)3)8-7-20(29)31(12-17,27(34)35)28(36)37/h14,16-20,22-26,33,38H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37)(H,39,40,41)(H,42,43,44)/t16-,17-,18+,19-,20-,22+,23+,24-,25+,26+,29-,30-/m1/s1
• InChIKey: CYBVQIBJEFQVPD-GWDNDVLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,7R,9R,10R,13R,15S)-7-{[(2S,3R,4R,5S,6S)-6-(hydroperoxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5,5-dicarboxylic acid
• IUPAC Traditional name: @carboxyatractyloside
• Synonyms: Carboxyatractyloside

Database IDs

• CAS Number: 33286-30-5
• PubChem SID: 46505904; 160965618
• PubChem CID: 46936378

CALCULATED PROPERTIES

JChem

• Acid pKa: -2.3183782
• H Acceptors: 16
• H Donor: 6
• LogD (pH = 5.5): -5.6166463
• LogD (pH = 7.4): -7.598823
• Log P: -1.545624
• Molar Refractivity: 168.7869 cm^3
• Polarizability: 70.42246 Å^3
• Polar Surface Area: 296.25 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.38
• LOG S: -2.56
• Solubility (Water): 2.17e+00 g/l

DETAILS

DrugBank - DB02426

Drug information: experimental