17-(1,5-Dimethyl-hexyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (24,25-dihydrolanosterol)

ID: ALA132906

PubChem CID: 65581

Max Phase: Preclinical

Molecular Formula: C30H52O

Molecular Weight: 428.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3

Standard InChI:  InChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25?,26+,28-,29-,30+/m1/s1

Standard InChI Key:  MBZYKEVPFYHDOH-XCEBNUDKSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    2.4542   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -2.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.0292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625    1.3833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  1  1  0
  6 14  1  0
  7  6  1  0
  8  5  1  0
  9  1  1  0
 10  5  1  0
 11 10  1  0
 12  2  1  0
 13  4  1  0
 14 12  1  0
 15  9  1  0
 16  7  1  0
 17 13  1  0
 18  8  1  0
  1 19  1  6
  4 20  1  1
  5 21  1  1
 22  7  1  0
  7 23  1  0
 16 24  1  1
 25 26  1  0
 26 18  1  0
 27 18  1  0
 28 25  1  0
 29 28  1  0
 30 29  1  0
 31 29  1  0
  8 32  1  6
 18 33  1  1
 15  8  1  0
 11  3  1  0
  6  4  1  0
 17 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA132906

   Lanosterol, 24,25-dihydro-

Molecule Features

Natural Product: Yes

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: 428.75

Molecular Weight (Monoisotopic): 428.4018

AlogP: 8.56

#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: 8.11

CX LogD: 8.11

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: 3.00

References

1. Frye LL, Cusack KP, Leonard DA..  (1993)  32-Methyl-32-oxylanosterols: dual-action inhibitors of cholesterol biosynthesis.,  36  (3): [PMID:8426367] [10.1021/jm00055a012]

Source

Source(1):

• Scientific Literature