[24-Nor-9,10-seco-5,7,10-(19)-cholestatriene-3beta,25-diol

ID: ALA3275634

PubChem CID: 90679171

Max Phase: Preclinical

Molecular Formula: C26H42O2

Molecular Weight: 386.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCC(C)(C)O)CC[C@@H]12

Standard InChI:  InChI=1S/C26H42O2/c1-18-8-11-22(27)17-21(18)10-9-20-7-6-15-26(5)23(12-13-24(20)26)19(2)14-16-25(3,4)28/h9-10,19,22-24,27-28H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22+,23-,24+,26-/m1/s1

Standard InChI Key:  DEBFVLKHIKOBPN-CMOHYRQESA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    5.2162  -29.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815  -30.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815  -31.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2162  -30.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7903  -30.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033  -30.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0054  -29.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7903  -31.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033  -29.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033  -31.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7903  -29.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0054  -30.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686  -30.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941  -29.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686  -31.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4433  -28.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2162  -28.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557  -30.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557  -31.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9279  -31.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6555  -27.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2684  -28.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0054  -27.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4806  -27.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8784  -27.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2162  -31.1066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8304  -29.2047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0753  -29.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9106  -28.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3052  -27.7281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  2  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
 19 20  1  1
 21 22  1  0
 22 16  1  0
 16 23  1  6
 24 21  1  0
 25 24  1  0
  4 26  1  6
  7 27  1  6
 12 14  1  0
  6  5  1  0
  3  8  2  0
 15 19  1  0
  2 28  2  0
 24 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275634

   (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-5-hydroxy-5-methylhexan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-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: 386.62

Molecular Weight (Monoisotopic): 386.3185

AlogP: 6.34

#Rotatable Bonds: 5

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: 2.76

References

1. Johnson RL, Carey SC, Norman AW, Okamura WH..  (1977)  Studies on vitamin D (calciferol) and its analogues. 10. Side-chain analogues of 25-hydroxyvitamin D3.,  20  (1): [PMID:833826] [10.1021/jm00211a002]

Source

Source(1):

• Scientific Literature