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

ID: ALA290479

Chembl Id: CHEMBL290479

PubChem CID: 44288894

Max Phase: Preclinical

Molecular Formula: C24H30F6O3

Molecular Weight: 480.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H30F6O3/c1-15-16(13-18(31)14-19(15)32)7-5-8-17-9-12-21(4,20(17,2)3)10-6-11-22(33,23(25,26)27)24(28,29)30/h5,7-8,17-19,31-33H,1,9-10,12-14H2,2-4H3/b8-5+,16-7-/t17-,18-,19+,21+/m1/s1

Standard InChI Key:  YABIUJHNICTUHY-WJFQVCTQSA-N

Alternative Forms

1. Parent:

   

   ALA290479

   (1R,3S,5Z)-4-methylidene-5-[(E)-3-[(1S,3R)-2,2,3-trimethyl-3-[5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pent-2-ynyl]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: 480.49

Molecular Weight (Monoisotopic): 480.2099

AlogP: 5.23

#Rotatable Bonds: 3

Polar Surface Area: 60.69

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.43

CX Basic pKa:

CX LogP: 4.63

CX LogD: 3.62

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: 1.35

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