(4R)-4-[(1R,2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-10-en-14-yl]pentanoic acid

• ChemBase ID: 105399
• Molecular Formular: C24H38O4
• Molecular Mass: 390.55612
• Monoisotopic Mass: 390.2770097
• SMILES: C[C@H](CCC(=O)O)[C@H]1CCC2=C3CC[C@@H]4C[C@@H](CC[C@]4(C)[C@H]3C[C@@H]([C@]12C)O)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CCC1=C3[C@@]([C@H](C[C@H]21)O)(C)[C@H](CC3)[C@@H](CCC(=O)O)C)C
• InChI: InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-16,18,20-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,18-,20+,21+,23+,24-/m1/s1
• InChIKey: XWJTYEGVQBFZHI-IMPNNSMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1R,2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-10-en-14-yl]pentanoic acid; (4R)-4-[(1R,2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadec-10-en-14-yl]pentanoic acid
• IUPAC Traditional name: apocholic acid
• Synonyms: Apocholic acid; 3α,12α-Dihydroxy-5β,8(14)-cholen-24-oic acid; 3α,12α-Dihydroxy-5β-chol-8(14)en-24-oic acid; 5β,8(14)-Cholen-24-oic acid-3α,12α-diol; APOCHOLIC ACID; 3α,12α-二羟基-5β-胆甾-8(14)烯-24-酸; 5β,8(14)-胆烯-24-酸-3α,12α-二醇; 去水胆酸; 原胆酸

Database IDs

• CAS Number: 641-81-6
• MDL Number: MFCD00003622
• PubChem SID: 24855723; 162093605
• PubChem CID: 101818

CALCULATED PROPERTIES

• Acid pKa: 4.614775
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.4046028
• LogD (pH = 7.4): 0.6280378
• Log P: 3.342022
• Molar Refractivity: 109.7802 cm^3
• Polarizability: 43.52601 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 171-174°C; 175-176 °C(lit.)
• Optical Rotation: [α]25/D +45.0°, c = 1 in methanol

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: FZ5075000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C24H38O4

DETAILS

MP Biomedicals - 02190021

Dehydration product of cholic acid, with
C₈-14 double bond that is inert to most reagents and cannot be catalytically hydrogenated.