24-nor-25-hydroxy-5,6-trans-vitamin D3

ID: ALA3250187

PubChem CID: 90674309

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-QFNXGBIASA-N

Molfile:  

     RDKit          2D

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    8.5445   -3.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7263   -2.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -3.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8044   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3044   -1.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7983   -3.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1148   -8.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362   -2.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3234   -3.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1029   -4.0532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2013   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3220   -4.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362   -5.1533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6209   -3.1644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2203   -3.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4028   -8.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1118   -4.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9733   -3.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5514   -2.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8318   -3.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8268   -7.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -4.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8294   -4.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8294   -5.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1148   -5.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1148   -6.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4028   -7.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5340   -8.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6939   -6.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  2  1  0
 13  5  1  0
 26 25  1  0
 22 27  1  0
 25 24  2  0
 28 27  1  0
 19  7  1  0
  5 10  1  0
 20 19  1  0
 27 26  2  0
 28 17  1  0
 21  4  1  0
  4 18  1  0
 23 14  1  6
 10 11  1  6
 24 18  1  0
  2 23  1  0
 17  8  1  0
  2  9  1  1
  7 12  1  0
  3 20  1  0
  8  1  1  0
  7 16  1  0
  1 22  1  0
 10  3  1  0
  7 15  1  0
  2 21  1  0
 23 13  1  0
  3  6  1  6
 24 23  1  0
  1 29  1  1
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250187

   (1S,3E)-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. 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