2-[(1S,2S,5R,6S,7S,10S,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

• ChemBase ID: 165954
• Molecular Formular: C31H48O5
• Molecular Mass: 500.70982
• Monoisotopic Mass: 500.35017464
• SMILES: C1[C@H]([C@H]([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2([C@@H](CC1)/C(=C(\CCC=C(C)C)/C(=O)O)/[C@@H](C2)OC(=O)C)C)C)C)C)O
• Canonical SMILES: CC(=O)O[C@@H]1C[C@]2([C@H](/C/1=C(/C(=O)O)\CCC=C(C)C)CC[C@@H]1[C@]2(C)CC[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C
• InChI: InChI=1S/C31H48O5/c1-18(2)9-8-10-21(28(34)35)27-23-11-12-26-29(5)15-14-24(33)19(3)22(29)13-16-30(26,6)31(23,7)17-25(27)36-20(4)32/h9,19,22-26,33H,8,10-17H2,1-7H3,(H,34,35)/b27-21-/t19-,22-,23-,24+,25+,26-,29-,30-,31-/m0/s1
• InChIKey: XIQFIBYNKGFJIX-SXBPZAMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,6S,7S,10S,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid
• IUPAC Traditional name: 2-[(1S,2S,5R,6S,7S,10S,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid
• Synonyms: (3α,4α,8α,9β,13α,14β,16β,17Z)-16-(Acetyloxy)-3-hydroxy-29-nordammara-17(20),24-dien-21-oic Acid; 11-Deoxy Fusidic Acid

Database IDs

• CAS Number: 1013937-16-0
• PubChem SID: 162260087
• PubChem CID: 71315478

CALCULATED PROPERTIES

• Acid pKa: 4.745754
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.9067163
• LogD (pH = 7.4): 3.129809
• Log P: 5.7306786
• Molar Refractivity: 142.5308 cm^3
• Polarizability: 56.319717 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D236300

11-Deoxy Fusidic Acid is an impurity of the bacteriostatic antibiotic, Fusidic Acid (v).