[22,23,24-Trinor-9,10-seco-5,7,10(19)-cholestatriene-3beta,25-diol

ID: ALA3275632

PubChem CID: 90679169

Max Phase: Preclinical

Molecular Formula: C24H38O2

Molecular Weight: 358.57

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

Standard InChI:  InChI=1S/C24H38O2/c1-16-8-11-20(25)15-19(16)10-9-18-7-6-14-24(5)21(12-13-22(18)24)17(2)23(3,4)26/h9-10,17,20-22,25-26H,1,6-8,11-15H2,2-5H3/b18-9+,19-10-/t17-,20-,21+,22-,24+/m0/s1

Standard InChI Key:  FTTPMMLZIQVGNY-RVTIKUOOSA-N

Molfile:  

     RDKit          2D

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   14.0635  -23.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280  -24.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280  -25.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0635  -24.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6371  -24.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3503  -24.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8528  -22.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6371  -25.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3503  -22.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3503  -25.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6371  -23.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8528  -24.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2149  -24.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3416  -23.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2149  -25.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2909  -22.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0635  -22.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5017  -24.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5017  -25.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7737  -25.6893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5035  -21.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1163  -22.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8528  -21.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0635  -24.8640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6782  -22.9613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9219  -23.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5477  -22.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9408  -22.2305    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
  4 24  1  6
  7 25  1  6
 12 14  1  0
  6  5  1  0
  3  8  2  0
 15 19  1  0
  2 26  2  0
 22 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275632

   (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2S)-3-hydroxy-3-methylbutan-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: 358.57

Molecular Weight (Monoisotopic): 358.2872

AlogP: 5.56

#Rotatable Bonds: 3

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: 4.40

CX LogD: 4.40

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 2.49

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