[20-Methyl-9,10-seco-5,7,10(19)-pregnatriene-3beta,20-diol

ID: ALA3275631

PubChem CID: 90679168

Max Phase: Preclinical

Molecular Formula: C22H34O2

Molecular Weight: 330.51

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

Standard InChI:  InChI=1S/C22H34O2/c1-15-7-10-18(23)14-17(15)9-8-16-6-5-13-22(4)19(16)11-12-20(22)21(2,3)24/h8-9,18-20,23-24H,1,5-7,10-14H2,2-4H3/b16-8+,17-9-/t18-,19-,20+,22-/m0/s1

Standard InChI Key:  JHTHNWHPKZQFFS-RPTOKDGXSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.4143  -22.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789  -24.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789  -25.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4143  -23.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880  -23.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -24.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2037  -22.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880  -25.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -22.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -25.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880  -22.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2037  -24.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657  -23.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6925  -23.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657  -25.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417  -22.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4143  -22.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525  -24.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525  -25.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245  -25.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4671  -21.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2037  -21.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4143  -24.6180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727  -23.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0494  -21.2842    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
  7 16  1  1
  1 17  1  1
 18 13  1  0
 19 18  1  0
 19 20  1  1
 21 16  1  0
 16 22  1  0
  4 23  1  6
 12 14  1  0
  6  5  1  0
  3  8  2  0
 15 19  1  0
  2 24  2  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275631

   (1S,3Z)-3-[(2E)-2-[(1S,3aS,7aS)-1-(2-hydroxypropan-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: 330.51

Molecular Weight (Monoisotopic): 330.2559

AlogP: 4.93

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 2.78

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