(20R)-25-Bromo-27-norcholest-5-en-3beta-ol

ID: ALA2048323

PubChem CID: 70686268

Max Phase: Preclinical

Molecular Formula: C26H43BrO

Molecular Weight: 451.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Br)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C26H43BrO/c1-17(6-5-7-18(2)27)22-10-11-23-21-9-8-19-16-20(28)12-14-25(19,3)24(21)13-15-26(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3/t17-,18?,20+,21+,22-,23+,24+,25+,26-/m1/s1

Standard InChI Key:  LTFMGHWBBACKDO-JVMDNGGPSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   21.2167  -18.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0792  -19.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0792  -20.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2167  -19.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7917  -19.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042  -19.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0042  -18.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7917  -21.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042  -18.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042  -20.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7917  -18.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0042  -19.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3667  -19.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4917  -19.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3667  -21.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4417  -17.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2167  -17.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6542  -19.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6542  -20.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0792  -19.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9292  -21.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6542  -16.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2667  -17.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0042  -16.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4792  -16.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8792  -16.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7042  -16.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042  -19.0583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2167  -20.2958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8292  -18.3917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7917  -20.2958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4490  -15.4918    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5 11  1  0
  6  4  1  0
  7  1  1  0
  8 10  1  0
  9  1  1  0
 10  6  1  0
 11  9  1  0
 12  4  1  0
 13  2  1  0
 14  7  1  0
 15  3  1  0
 16  7  1  0
  1 17  1  1
 18 13  1  0
 19 18  1  0
  2 20  1  1
 19 21  1  1
 22 23  1  0
 23 16  1  0
 16 24  1  6
 25 22  1  0
 26 25  1  0
 27 26  1  0
  6 28  1  1
  4 29  1  6
  7 30  1  6
  5 31  1  6
 12 14  1  0
  6  5  1  0
  3  8  2  0
 15 19  1  0
 26 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2048323

   (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-bromoheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-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: 451.53

Molecular Weight (Monoisotopic): 450.2497

AlogP: 7.52

#Rotatable Bonds: 5

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: 6.90

CX LogD: 6.90

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: 2.53

References

1. Johnston JB, Singh AA, Clary AA, Chen CK, Hayes PY, Chow S, De Voss JJ, Ortiz de Montellano PR..  (2012)  Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.,  20  (13): [PMID:22647881] [10.1016/j.bmc.2012.05.003]

Source

Source(1):

• Scientific Literature