(1R,3R)-5-[2-[(1R,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

ID: ALA36592

Chembl Id: CHEMBL36592

PubChem CID: 10180182

Max Phase: Preclinical

Molecular Formula: C27H44O3

Molecular Weight: 416.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1Alpha,25-Dihydroxy-Vitamin D | CHEMBL36592|1Alpha,25-Dihydroxy-Vitamin D|AKOS005146503

Canonical SMILES:  C=C1/C(=C\C=C2/CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O)C[C@@H](O)C[C@H]1O

Standard InChI:  InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24?,25-,27-/m1/s1

Standard InChI Key:  GMRQFYUYWCNGIN-GSMZWGLTSA-N

Alternative Forms

1. Parent:

   

   ALA36592

   1Alpha,25-Dihydroxy-Vitamin D

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 416.65

Molecular Weight (Monoisotopic): 416.3290

AlogP: 5.70

#Rotatable Bonds: 6

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.35

CX LogD: 4.35

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: 2.65

References

1. Ono Y, Watanabe H, Akira K, Kubodera N, Okano T, Tsugawa N, Kobayashi T.  (1994)  Synthesis and biological character of 1-hydroxylated vitamin D3 Analogues,  4  (12): [10.1016/S0960-894X(01)80525-4]

2. Garay E, Jankowski P, Lizano P, Marczak S, Maehr H, Adorini L, Uskokovic MR, Studzinski GP..  (2007)  Calcitriol derivatives with two different side-chains at C-20. Part 4: further chain modifications that alter VDR-dependent monocytic differentiation potency in human leukemia cells.,  15  (13): [PMID:17485214] [10.1016/j.bmc.2007.04.034]

Source

Source(1):

• Scientific Literature