(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid

• ChemBase ID: 163546
• Molecular Formular: C23H34O4
• Molecular Mass: 374.51366
• Monoisotopic Mass: 374.24570957
• SMILES: C1C/C(=C\C=C/2\C[C@H](C[C@@H](C2=C)O)O)/[C@H]2[C@](C1)([C@H](CC2)[C@@H](CC(=O)O)C)C
• Canonical SMILES: OC(=O)C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)C[C@@H](C1=C)O)C
• InChI: InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18-,19-,20+,21+,23-/m1/s1
• InChIKey: MBLYZRMZFUWLOZ-ZTIKAOTBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid
• IUPAC Traditional name: calcitroic acid
• Synonyms: (βR,1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-Dihydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-β,7a-dimethyl-1H-indene-1-propanoic Acid; (1α,3β,5Z,7E)-1,3-Dihydroxy-24-nor-9,10-secochola-5,7,10(19)-trien-23-oic Acid; 1α-Hydroxycalcioic Acid; MC 1235; Calcitroic Acid

Database IDs

• CAS Number: 71204-89-2
• PubChem SID: 162257681
• PubChem CID: 9547273

CALCULATED PROPERTIES

• Acid pKa: 4.9145412
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.1956425
• LogD (pH = 7.4): 0.43158337
• Log P: 2.880889
• Molar Refractivity: 108.0102 cm^3
• Polarizability: 41.927895 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C144550

Calcitroic Acid is a major metabolite of Calcitriol (C144500).

REFERENCES

• Esvelt, R.P. et al.: Arch. Biochem. Biophys., 206, 403 (1981)
• Onisko, B.L. et al.: Biochemistry, 19, 4124 (1981)
• Reddy, G.S. et al.: Biochemistry, 28, 1763 (1981)