(1R,3S)-4-Methylene-5-[(E)-3-[(1S,3R)-2,2,3-trimethyl-3-((Z)-6,6,6-trifluoro-5-hydroxy-5-trifluoromethyl-hex-1-enyl)-cyclopentyl]-prop-2-en-(Z)-ylidene]-cyclohexane-1,3-diol

ID: ALA289830

Chembl Id: CHEMBL289830

PubChem CID: 44289085

Max Phase: Preclinical

Molecular Formula: C25H34F6O3

Molecular Weight: 496.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1/C(=C\C=C\[C@@H]2CC[C@](C)(/C=C\CCC(O)(C(F)(F)F)C(F)(F)F)C2(C)C)C[C@@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C25H34F6O3/c1-16-17(14-19(32)15-20(16)33)8-7-9-18-10-13-22(4,21(18,2)3)11-5-6-12-23(34,24(26,27)28)25(29,30)31/h5,7-9,11,18-20,32-34H,1,6,10,12-15H2,2-4H3/b9-7+,11-5-,17-8-/t18-,19-,20+,22+/m1/s1

Standard InChI Key:  QZYTWOMDINVXGJ-ZTPRGVDQSA-N

Alternative Forms

1. Parent:

   

   ALA289830

   (1R,3S,5Z)-4-methylidene-5-[(E)-3-[(1S,3R)-2,2,3-trimethyl-3-[(Z)-6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-1-enyl]cyclopentyl]prop-2-enylidene]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: 496.53

Molecular Weight (Monoisotopic): 496.2412

AlogP: 6.18

#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: 7.98

CX Basic pKa:

CX LogP: 4.97

CX LogD: 4.87

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: 1.57

References

1. Wu Y, Sabbe K, De Clercq P, Vandewalle M, Bouillon R, Verstuyf A..  (2002)  Vitamin D(3): synthesis of seco C-9,11,21-trisnor-17-methyl-1 alpha, 25-dihydroxyvitamin D(3) analogues.,  12  (12): [PMID:12039578] [10.1016/s0960-894x(02)00221-4]

Source

Source(1):

• Scientific Literature