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

ID: ALA3351011

Chembl Id: CHEMBL3351011

PubChem CID: 5283780

Max Phase: Preclinical

Molecular Formula: C28H46O3

Molecular Weight: 430.67

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](C)[C@H]1O

Standard InChI:  InChI=1S/C28H46O3/c1-18(9-7-15-27(4,5)31)23-13-14-24-21(10-8-16-28(23,24)6)11-12-22-17-25(29)20(3)26(30)19(22)2/h11-12,18,20,23-26,29-31H,2,7-10,13-17H2,1,3-6H3/b21-11+,22-12-/t18-,20-,23-,24+,25-,26+,28-/m1/s1

Standard InChI Key:  PSWKLSOBPNHZSY-CYHSQAEGSA-N

Alternative Forms

1. Parent:

   

   ALA3351011

   2beta-methyl-1beta,25-dihydroxyvitamin D3/2beta-methyl-1beta,25-dihydroxycholecalciferol

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: 430.67

Molecular Weight (Monoisotopic): 430.3447

AlogP: 5.95

#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: 4.83

CX LogD: 4.83

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 2.43

References

1. Konno K, Maki S, Fujishima T, Liu Z, Miura D, Chokki M, Takayama H..  (1998)  A novel and practical route to A-ring enyne synthon for 1 alpha,25-dihydroxyvitamin D3 analogs: synthesis of A-ring diastereomers of 1 alpha,25-dihydroxyvitamin D2 and 3-methyl-1,25-dihydroxyvitamin D3.,  8  (2): [PMID:9871644] [10.1016/s0960-894x(97)10204-9]

2. Fujishima T, Liu Z, Miura D, Chokki M, Ishizuka S, Konno K, Takayama H..  (1998)  Synthesis and biological activity of 2-methyl-20-epi analogues of 1 alpha,25-dihydroxyvitamin D3.,  8  (16): [PMID:9873502] [10.1016/s0960-894x(98)00363-1]

3. Konno K, Fujishima T, Maki S, Liu Z, Miura D, Chokki M, Ishizuka S, Yamaguchi K, Kan Y, Kurihara M, Miyata N, Smith C, DeLuca HF, Takayama H..  (2000)  Synthesis, biological evaluation, and conformational analysis of A-ring diastereomers of 2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20.,  43  (22): [PMID:11063621] [10.1021/jm000261j]

4. Konno K, Fujishima T, Maki S, Liu Z, Miura D, Chokki M, Ishizuka S, Yamaguchi K, Kan Y, Kurihara M, Miyata N, Smith C, DeLuca HF, Takayama H..  (2000)  Synthesis, biological evaluation, and conformational analysis of A-ring diastereomers of 2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20.,  43  (22): [PMID:11063621] [10.1021/jm000261j]

Source

Source(1):

• Scientific Literature