(3S,4S,5S,10R,13R,17R)-17-((R)-1,5-Dimethyl-hexyl)-4-(4-fluoro-benzyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol

ID: ALA3137902

PubChem CID: 10051542

Max Phase: Preclinical

Molecular Formula: C34H53FO

Molecular Weight: 496.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4[C@H](Cc5ccc(F)cc5)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C34H53FO/c1-22(2)7-6-8-23(3)28-15-16-29-26-13-14-30-27(21-24-9-11-25(35)12-10-24)32(36)18-20-34(30,5)31(26)17-19-33(28,29)4/h9-12,22-23,26-32,36H,6-8,13-21H2,1-5H3/t23-,26+,27+,28-,29+,30+,31+,32+,33-,34+/m1/s1

Standard InChI Key:  XBFYWAPHHGJTKT-PRYSFELPSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  1  0  0  0  0  0999 V2000
   11.4115   -8.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5767   -7.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1332   -8.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5598   -8.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4117   -9.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8495   -8.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7014   -9.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3672   -6.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8548   -6.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7010   -8.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1330   -7.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1165   -9.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3504   -8.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8382   -9.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8429   -7.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7016  -10.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9967   -9.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9965   -8.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7738   -6.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4063  -10.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1993   -7.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5708   -6.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216  -11.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5263  -12.1847    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.1717   -9.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3951  -11.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1167  -10.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8214  -10.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1113  -12.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0172   -6.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5874   -6.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3497   -5.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422   -6.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2548   -7.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8539   -8.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0797   -7.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2933   -8.5796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4071  -10.2935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2685   -7.5552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7109   -8.9832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6560   -9.0681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3676   -6.9458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  1  3  1  0
  6  4  1  0
  1  5  1  0
  3  6  1  0
  5  7  1  0
  2  8  1  0
  9 11  1  0
  1 10  1  0
  3 11  1  0
  5 12  1  0
  4 13  1  0
 14 12  1  0
 15 13  1  0
  7 16  1  6
 17 18  1  0
 18 10  1  0
  8 19  1  1
 20 16  1  0
  1 21  1  1
  2 22  1  1
 23 28  1  0
 24 23  1  0
 17 25  1  1
 26 20  2  0
 27 20  1  0
 28 27  2  0
 29 26  1  0
 30 31  1  0
 19 31  1  0
 19 32  1  6
 33 30  1  0
 34 33  1  0
 35 34  1  0
 36 34  1  0
 17 37  1  6
  5 38  1  6
  7 17  1  0
  6 14  1  0
  4  2  1  0
  8 15  1  0
 23 29  2  0
  3 39  1  6
  6 40  1  1
  4 41  1  6
  8 42  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3137902

   (3S,4S,5S,8S,9S,10R,13R,14S,17R)-4-[(4-fluorophenyl)methyl]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

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: 496.80

Molecular Weight (Monoisotopic): 496.4080

AlogP: 9.08

#Rotatable Bonds: 7

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 9.60

CX LogD: 9.60

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.40

Np Likeness Score: 1.57

References

1. Lin HS, Rampersaud AA, Archer RA, Pawlak JM, Beavers LS, Schmidt RJ, Kauffman RF, Bensch WR, Bumol TF, Apelgren LD..  (1995)  Synthesis and biological evaluation of a new series of sterols as potential hypocholesterolemic agents.,  38  (2): [PMID:7830271] [10.1021/jm00002a010]

Source

Source(1):

• Scientific Literature