[23,24-Dinor-9,10-seco-5,7,10(19)-cholestatriene-3beta,25-diol

ID: ALA3275633

PubChem CID: 90679170

Max Phase: Preclinical

Molecular Formula: C25H40O2

Molecular Weight: 372.59

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)CC(C)(C)O)CC[C@@H]12

Standard InChI:  InChI=1S/C25H40O2/c1-17-8-11-21(26)15-20(17)10-9-19-7-6-14-25(5)22(12-13-23(19)25)18(2)16-24(3,4)27/h9-10,18,21-23,26-27H,1,6-8,11-16H2,2-5H3/b19-9+,20-10-/t18-,21+,22-,23+,25-/m1/s1

Standard InChI Key:  ITUOXRNSZJYYMC-ILGLOGIYSA-N

Molfile:  

     RDKit          2D

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   21.0433  -23.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0433  -24.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1785  -23.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7523  -23.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4654  -23.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9679  -22.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7523  -25.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4654  -22.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4654  -24.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.3301  -23.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4567  -22.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3301  -25.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4059  -21.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1785  -21.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6170  -23.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6170  -24.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8890  -25.0334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6185  -20.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2312  -21.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9679  -20.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4439  -20.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1785  -24.2081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.7932  -22.3055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0371  -22.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1845  -20.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0265  -20.1367    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
  4 25  1  6
  7 26  1  6
 12 14  1  0
  6  5  1  0
  3  8  2  0
 15 19  1  0
  2 27  2  0
 21 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275633

   (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-4-hydroxy-4-methylpentan-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: 372.59

Molecular Weight (Monoisotopic): 372.3028

AlogP: 5.95

#Rotatable Bonds: 4

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: 4.77

CX LogD: 4.77

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 2.55

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