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

ID: ALA212940

Chembl Id: CHEMBL212940

PubChem CID: 10062746

Max Phase: Preclinical

Molecular Formula: C30H50O4

Molecular Weight: 474.73

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](CCCO)[C@@H]1O

Standard InChI:  InChI=1S/C30H50O4/c1-20(9-6-16-29(3,4)34)25-14-15-26-22(10-7-17-30(25,26)5)12-13-23-19-27(32)24(11-8-18-31)28(33)21(23)2/h12-13,20,24-28,31-34H,2,6-11,14-19H2,1,3-5H3/b22-12+,23-13-/t20-,24+,25-,26+,27-,28-,30-/m1/s1

Standard InChI Key:  QOVWEUHJARWCDV-RQSRSJTKSA-N

Alternative Forms

1. Parent:

   

   ALA212940

   2alpha-(3-Hydroxypropyl)-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: 474.73

Molecular Weight (Monoisotopic): 474.3709

AlogP: 5.70

#Rotatable Bonds: 9

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: 2.42

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]

4. Honzawa S, Yamamoto Y, Yamashita A, Sugiura T, Kurihara M, Arai MA, Kato S, Kittaka A..  (2008)  The 2alpha-(3-hydroxypropyl) group as an active motif in vitamin D3 analogues as agonists of the mutant vitamin D receptor (Arg274Leu).,  16  (6): [PMID:18248997] [10.1016/j.bmc.2007.12.039]

5. Matsuo M, Hasegawa A, Takano M, Saito H, Kakuda S, Chida T, Takagi K, Ochiai E, Horie K, Harada Y, Takimoto-Kamimura M, Takenouchi K, Sawada D, Kittaka A..  (2013)  Synthesis of 2α-heteroarylalkyl active vitamin d3 with therapeutic effect on enhancing bone mineral density in vivo.,  4  (7): [PMID:24900728] [10.1021/ml400098w]

Source

Source(1):

• Scientific Literature