(1R,2S,3S)-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: ALA215541

Chembl Id: CHEMBL215541

PubChem CID: 5283797

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-GEMNOXHFSA-N

Alternative Forms

1. Parent:

   

   ALA215541

   2alpha-Methyl-1alpha,25-dihydroxy-vitamin 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: 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. 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. 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]

3. 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]

4. 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]

5. 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]

6. 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]

7. 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]

8. Fujishima T, Nozaki T, Suenaga T..  (2013)  Design and synthesis of novel 1,25-dihydroxyvitamin D3 analogues having a spiro-oxetane fused at the C2 position in the A-ring.,  21  (17): [PMID:23845283] [10.1016/j.bmc.2013.06.032]

Source

Source(1):

• Scientific Literature