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

ID: ALA3350836

Chembl Id: CHEMBL3350836

PubChem CID: 10502779

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)[C@H](C)CCC(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C28H46O3/c1-18(13-15-27(4,5)31)19(2)24-11-12-25-21(8-7-14-28(24,25)6)9-10-22-16-23(29)17-26(30)20(22)3/h9-10,18-19,23-26,29-31H,3,7-8,11-17H2,1-2,4-6H3/b21-9+,22-10-/t18-,19+,23-,24-,25+,26+,28-/m1/s1

Standard InChI Key:  QPTWRYOQVNBAPE-MWIOODTKSA-N

Alternative Forms

1. Parent:

   

   ALA3350836

   (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2S,3R)-6-hydroxy-3,6-dimethylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-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: 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: 4.64

CX LogD: 4.64

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 2.58

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. Masuno H, Yamamoto K, Wang X, Choi M, Ooizumi H, Shinki T, Yamada S..  (2002)  Rational design, synthesis, and biological activity of novel conformationally restricted vitamin D analogues, (22R)- and (22S)-22-ethyl-1,25-dihydroxy-23,24-didehydro-24a,24b-dihomo-20-epivitamin D(3).,  45  (9): [PMID:11960494] [10.1021/jm0105631]

3. Yamamoto K, Sun WY, Ohta M, Hamada K, DeLuca HF, Yamada S..  (1996)  Conformationally restricted analogs of 1 alpha, 25-dihydroxyvitamin D3 and its 20-epimer: compounds for study of the three-dimensional structure of vitamin D responsible for binding to the receptor.,  39  (14): [PMID:8709103] [10.1021/jm9600048]

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