25-thia-27-norcholest-4-en-3-one

ID: ALA2048327

PubChem CID: 70688385

Max Phase: Preclinical

Molecular Formula: C25H40OS

Molecular Weight: 388.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H40OS/c1-17(6-5-15-27-4)21-9-10-22-20-8-7-18-16-19(26)11-13-24(18,2)23(20)12-14-25(21,22)3/h16-17,20-23H,5-15H2,1-4H3/t17-,20+,21-,22+,23+,24+,25-/m1/s1

Standard InChI Key:  KQWZVOYEUWXTLN-XBCZOFBYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    7.9167    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1417    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -2.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3542    1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9667    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1792    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5792    2.6083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4042    2.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -0.2542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -1.4917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -1.4917    0.0000 H   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  2  0
 16  7  1  0
  1 17  1  1
 18 13  1  0
 19 18  1  0
  2 20  1  1
 19 21  2  0
 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  1  0
 15 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2048327

   (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-5-methylsulfanylpentan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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: 388.66

Molecular Weight (Monoisotopic): 388.2800

AlogP: 6.91

#Rotatable Bonds: 5

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.71

CX LogD: 6.71

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 2.08

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