24-nor-1alpha,25-dihydroxyvitamin D3

ID: ALA3250185

PubChem CID: 9547305

Max Phase: Preclinical

Molecular Formula: C26H42O3

Molecular Weight: 402.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CCC(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C26H42O3/c1-17(12-14-25(3,4)29)22-10-11-23-19(7-6-13-26(22,23)5)8-9-20-15-21(27)16-24(28)18(20)2/h8-9,17,21-24,27-29H,2,6-7,10-16H2,1,3-5H3/b19-8+,20-9-/t17-,21-,22-,23+,24+,26-/m1/s1

Standard InChI Key:  NEPGKWAOGVSEMP-ZPURXJTESA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    8.7944   -6.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8028   -6.7096    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078   -8.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0089   -7.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0205   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2849   -5.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931   -6.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7372   -4.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5032   -6.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2171   -7.8175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6367   -5.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2301   -6.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5057   -7.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6607   -7.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0890   -4.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0860   -8.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9461   -8.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843   -7.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7921   -8.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2219   -6.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3725   -8.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0775   -6.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2256   -5.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3725   -6.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6607   -8.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4449   -5.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9926   -6.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5135   -5.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3725   -6.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7045   -4.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2596   -5.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 11  1  0
 25 17  1  1
 14 25  1  0
 16 19  2  0
 20  4  1  0
 28  1  1  0
 25 21  1  0
 12 20  1  0
  3 13  2  0
  4  9  1  0
 13 20  1  0
  5  6  1  0
  5 12  1  0
 14 24  1  0
 12 28  1  0
 11 26  1  0
 19  3  1  0
  7 13  1  0
 18 16  1  0
 21 16  1  0
 12 23  1  1
 20 10  1  6
  6 15  1  0
  7  1  1  0
 18 24  1  0
  9  5  1  0
  5  2  1  6
 26 27  1  0
 18 22  2  0
  6  8  1  6
 24 29  1  6
 26 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250185

   1alpha,25-dihydroxy-24-norvitamin D3/1alpha,25-dihydroxy-24-norcholecalciferol

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: 402.62

Molecular Weight (Monoisotopic): 402.3134

AlogP: 5.31

#Rotatable Bonds: 5

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 2.78

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