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

ID: ALA378356

Chembl Id: CHEMBL378356

PubChem CID: 10062705

Max Phase: Preclinical

Molecular Formula: C30H50O3

Molecular Weight: 458.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CCCC(C)(C)O)CC[C@@H]23)C[C@@H](O)[C@H](CCC)[C@@H]1O

Standard InChI:  InChI=1S/C30H50O3/c1-7-10-24-27(31)19-23(21(3)28(24)32)14-13-22-12-9-18-30(6)25(15-16-26(22)30)20(2)11-8-17-29(4,5)33/h13-14,20,24-28,31-33H,3,7-12,15-19H2,1-2,4-6H3/b22-13+,23-14-/t20-,24+,25-,26+,27-,28-,30-/m1/s1

Standard InChI Key:  GMZWKFJQHMQHAO-FMIFKYABSA-N

Alternative Forms

1. Parent:

   

   ALA378356

   2alpha-Propyl-1alpha,25-dihydroxyvitamin D3

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: 458.73

Molecular Weight (Monoisotopic): 458.3760

AlogP: 6.73

#Rotatable Bonds: 8

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: 5.72

CX LogD: 5.72

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: 2.33

References

1. Suhara Y, Nihei KI, Tanigawa H, Fujishima T, Konno K, Nakagawa K, Okano T, Takayama H..  (2000)  Syntheses and biological evaluation of novel 2alpha-substituted 1alpha,25-dihydroxyvitamin D3 analogues.,  10  (10): [PMID:10843234] [10.1016/s0960-894x(00)00189-x]

2. Honzawa S, Suhara Y, Nihei K, Saito N, Kishimoto S, Fujishima T, Kurihara M, Sugiura T, Waku K, Takayama H, Kittaka A..  (2003)  Concise synthesis and biological activities of 2alpha-alkyl- and 2alpha-(omega-hydroxyalkyl)-20-epi-1alpha,25-dihydroxyvitamin D3.,  13  (20): [PMID:14505658] [10.1016/s0960-894x(03)00739-x]

3. Hourai S, Fujishima T, Kittaka A, Suhara Y, Takayama H, Rochel N, Moras D..  (2006)  Probing a water channel near the A-ring of receptor-bound 1 alpha,25-dihydroxyvitamin D3 with selected 2 alpha-substituted analogues.,  49  (17): [PMID:16913708] [10.1021/jm0604070]

Source

Source(1):

• Scientific Literature