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

ID: ALA442191

Chembl Id: CHEMBL442191

PubChem CID: 5283739

Max Phase: Preclinical

Molecular Formula: C27H44O3

Molecular Weight: 416.65

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[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+/m0/s1

Standard InChI Key:  GMRQFYUYWCNGIN-WJBPREEXSA-N

Alternative Forms

1. Parent:

   

   ALA442191

   5-{2-[1-(5-Hydroxy-1,5-dimethyl-hexyl)-7A-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diol

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. Yamamoto K, Ooizumi H, Umesono K, Verstuyf A, Bouillon R, DeLuca HF, Shinki T, Suda T, Yamada S..  (1999)  Three-dimensional structure-function relationship of vitamin D: side chain location and various activities.,  9  (7): [PMID:10230636] [10.1016/s0960-894x(99)00129-8]

2. Norman AW, Manchand PS, Uskokovic MR, Okamura WH, Takeuchi JA, Bishop JE, Hisatake JI, Koeffler HP, Peleg S..  (2000)  Characterization of a novel analogue of 1alpha,25(OH)(2)-vitamin D(3) with two side chains: interaction with its nuclear receptor and cellular actions.,  43  (14): [PMID:10893309] [10.1021/jm0000160]

3. 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]

4. Zhou X, Zhu GD, Van Haver D, Vandewalle M, De Clercq PJ, Verstuyf A, Bouillon R..  (1999)  Synthesis, biological activity, and conformational analysis of four seco-D-15,19-bisnor-1alpha,25-dihydroxyvitamin D analogues, diastereomeric at C17 and C20.,  42  (18): [PMID:10479287] [10.1021/jm980736v]

5. Yamamoto K, Abe D, Yoshimoto N, Choi M, Yamagishi K, Tokiwa H, Shimizu M, Makishima M, Yamada S..  (2006)  Vitamin D receptor: ligand recognition and allosteric network.,  49  (4): [PMID:16480267] [10.1021/jm050795q]

Source

Source(1):

• Scientific Literature