27-norcholesta-4,25-dien-3-on

ID: ALA2048328

PubChem CID: 70694626

Max Phase: Preclinical

Molecular Formula: C27H42O

Molecular Weight: 382.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)CCC[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/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17,19,22-25H,1,6-16H2,2-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

Standard InChI Key:  SZQJWXYYHGBOKC-GYKMGIIDSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   17.2250    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0875   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0875   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2250   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8000   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5125   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0125    0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8000   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5125    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5125   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8000    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0125   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3750   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5000   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3750   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4500    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2250    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6625   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6625   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0875   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9375   -2.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6625    2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2750    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0125    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4875    2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8875    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7125    2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4500    3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5125   -0.0250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2250   -1.2625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8375    0.6417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8000   -1.2625    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
 28 26  2  0
  6 29  1  1
  4 30  1  6
  7 31  1  6
  5 32  1  6
 12 14  1  0
  6  5  1  0
  3  8  1  0
 15 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2048328

   Cholesten-4-en-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: 382.63

Molecular Weight (Monoisotopic): 382.3236

AlogP: 7.52

#Rotatable Bonds: 5

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.33

CX LogD: 7.33

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: 2.41

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