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

ID: ALA1214620

Chembl Id: CHEMBL1214620

PubChem CID: 9547653

Max Phase: Preclinical

Molecular Formula: C27H44O3

Molecular Weight: 416.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@H](O)CC(=C/C=C2\CCC[C@]3(C)[C@@H]([C@H](C)CCCC(C)(C)O)CC[C@@H]23)C[C@H]1O

Standard InChI:  InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)22-12-13-23-21(9-7-15-27(22,23)5)11-10-20-16-24(28)19(2)25(29)17-20/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b21-11+/t18-,22-,23+,24-,25-,27-/m1/s1

Standard InChI Key:  UHMPCVGLSKFXHR-JUTHDLPNSA-N

Alternative Forms

1. Parent:

   

   ALA1214620

   (1R,3R)-5-(2-((1R,3aS,7aR,E)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-2-methylenecyclohexane-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: 4.58

CX LogD: 4.58

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: 2.23

References

1. Sicinski RR, Prahl JM, Smith CM, DeLuca HF..  (1998)  New 1alpha,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogues.,  41  (23): [PMID:9804706] [10.1021/jm9802618]

2. Sakamaki Y, Inaba Y, Yoshimoto N, Yamamoto K..  (2010)  Potent antagonist for the vitamin D receptor: vitamin D analogues with simple side chain structure.,  53  (15): [PMID:20608741] [10.1021/jm100649d]

3. Flores A, Massarelli I, Thoden JB, Plum LA, DeLuca HF..  (2015)  A Methylene Group on C-2 of 24,24-Difluoro-19-nor-1α,25-dihydroxyvitamin D3 Markedly Increases Bone Calcium Mobilization in Vivo.,  58  (24): [PMID:26630444] [10.1021/acs.jmedchem.5b01564]

Source

Source(1):

• Scientific Literature