(3beta,5alpha)-3,21-Dihydroxypregnane-11,20-dione

ID: ALA2057978

Cas Number: 566-02-9

PubChem CID: 11695962

Max Phase: Preclinical

Molecular Formula: C21H32O4

Molecular Weight: 348.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)CO)[C@@]3(C)CC(=O)[C@@H]12

Standard InChI:  InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14-,15-,16+,19+,20-,21-/m0/s1

Standard InChI Key:  XWYBFXIUISNTQG-KMNUWYNSSA-N

Molfile:  

     RDKit          2D

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    6.8564  -20.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833  -21.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833  -22.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954  -22.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954  -21.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074  -21.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039  -22.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126  -22.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294  -22.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196  -21.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330  -21.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500  -19.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250  -20.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0633  -20.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499  -21.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8318  -21.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0583  -19.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417  -22.0292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6125  -22.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000  -20.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7695  -22.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958  -23.2458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3025  -19.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265  -19.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9254  -18.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1014  -18.6698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147  -19.9418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  2  5  1  0
  3  4  1  0
  6 10  1  0
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  1 14  1  0
  7  8  1  0
 14 18  1  1
  8  9  1  0
 15 19  1  6
  9 11  1  0
 11 20  1  1
 10 11  1  0
 10 21  1  6
  4  7  1  0
  6 22  1  1
  6  5  1  0
  3 23  1  1
  6  7  1  0
  7 24  1  6
  1 25  1  1
 10 13  1  0
 25 26  2  0
 11 15  1  0
 25 27  1  0
 14 12  1  0
 27 28  1  0
 12 13  1  0
 13 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2057978

   Allopregnane-3beta,21-diol-11,20-dione

Molecule Features

Natural Product: Yes

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: 348.48

Molecular Weight (Monoisotopic): 348.2301

AlogP: 2.75

#Rotatable Bonds: 2

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.86

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: 2.25

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: 2.46

References

1. Hamilton NM, Dawson M, Fairweather EE, Hamilton NS, Hitchin JR, James DI, Jones SD, Jordan AM, Lyons AJ, Small HF, Thomson GJ, Waddell ID, Ogilvie DJ..  (2012)  Novel steroid inhibitors of glucose 6-phosphate dehydrogenase.,  55  (9): [PMID:22506561] [10.1021/jm300317k]

Source

Source(1):

• Scientific Literature