4-{[(1S,2R,10R,11S,14R,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 5932
• Molecular Formular: C22H30O5
• Molecular Mass: 374.4706
• Monoisotopic Mass: 374.20932406
• SMILES: C1CC(=O)C=C2CC[C@@H]3[C@@H]([C@@H]12)CC[C@]1([C@H]3CC[C@H]1OC(=O)CCC(=O)O)C
• Canonical SMILES: OC(=O)CCC(=O)O[C@@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C22H30O5/c1-22-11-10-16-15-5-3-14(23)12-13(15)2-4-17(16)18(22)6-7-19(22)27-21(26)9-8-20(24)25/h12,15-19H,2-11H2,1H3,(H,24,25)/t15-,16+,17+,18-,19+,22-/m0/s1
• InChIKey: IRQUJNVGEAJGSD-KIEDKLRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S,2R,10R,11S,14R,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(1S,2R,10R,11S,14R,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxy}-4-oxobutanoic acid
• Synonyms: SUCCINIC ACID MONO-(13-METHYL-3-OXO-2,3,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL) ESTER

Database IDs

• PubChem SID: 160969357; 99444779
• PubChem CID: 5289054

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.310468
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.116613
• LogD (pH = 7.4): 0.37601727
• Log P: 3.3313644
• Molar Refractivity: 99.9995 cm^3
• Polarizability: 39.4706 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.96
• LOG S: -4.54
• Solubility (Water): 1.08e-02 g/l

DETAILS

DrugBank - DB08308

Drug information: experimental