25-hydroxy-5,6-trans-vitamin D3

ID: ALA3250186

Cas Number: 1233749-00-2

PubChem CID: 6506392

Max Phase: Preclinical

Molecular Formula: C27H44O2

Molecular Weight: 400.65

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

Standard InChI:  InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12+/t20-,23+,24-,25+,27-/m1/s1

Standard InChI Key:  JWUBBDSIWDLEOM-WIFPIRAHSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.8609   -5.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5779   -2.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7193   -2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5755   -4.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0695   -2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5755   -5.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609   -6.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5730   -7.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5730   -6.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0679   -4.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609   -8.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4724   -2.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504   -3.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489   -6.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823   -2.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2906   -3.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505   -1.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5442   -2.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3740   -4.3758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7912   -3.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823   -4.8841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2894   -4.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8490   -3.7841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9662   -3.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489   -7.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5632   -4.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8580   -4.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4400   -6.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2801   -8.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0
 24 23  1  6
 18  2  1  0
 26 21  1  0
  6  4  2  0
 18 24  1  0
 16  7  1  0
 16 27  1  0
 24 11  1  0
 26 22  1  0
 10  3  1  0
  8  9  1  0
 11 14  1  0
  3 20  1  0
  1  6  1  0
  5 13  1  0
 12  8  1  0
  5 25  1  6
  2 15  1  0
 13 10  1  0
 27 12  1  0
 26 28  1  0
  4 24  1  0
 20 26  1  0
 13 19  1  6
  4 29  1  0
  9  7  1  0
 15 29  1  0
  5 18  1  0
 18 17  1  1
 14  5  1  0
 16 30  2  0
  8 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3250186

   9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol

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: 400.65

Molecular Weight (Monoisotopic): 400.3341

AlogP: 6.73

#Rotatable Bonds: 6

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: 5.65

CX LogD: 5.65

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 2.63

References

1. Mouriño A, Blair P, Wecksler W, Johnson RL, Norman AW, Okamura WH..  (1978)  Studies on vitamin D (calciferol) and its analogues. 15. 24-Nor-1alpha,25-dihydroxyvitamin D3 and 24-nor-25-hydroxy-5,6-trans-vitamin D3.,  21  (10): [PMID:214553] [10.1021/jm00208a005]

Source

Source(1):

• Scientific Literature