17alpha-Methyl-4-androsten-11alpha,17beta-diol-3-one

ID: ALA1908006

Cas Number: 145-12-0

PubChem CID: 72061

Max Phase: Phase

Molecular Formula: C20H30O3

Molecular Weight: 318.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Anamidol | Oranabol | Oxymestrone | Theranabol | NSC-45048 | Oxymesterone|Anamidol|Oranabol|145-12-0|Theranabol|Aranabol|Oxymestrone|4-Hydroxy-17-methyltestosterone|NSC-45048|4R73K9MRMX|CHEBI:34903|4,17beta-Dihydroxy-17-methylandrost-4-en-3-one|4,17.beta.-Dihydroxy-17-methylandrost-4-en-3-one|Ossimesterone|Oximesterona|Oximesteronum|Oxymesteronum|Balnimax|Testosterone, 4-hydroxy-17-methyl-|4-Hydroxy-17.alpha.-methyltestosterone|Oranabol 10|Ossimesterone [DCIT]|UNII-4R73K9MRMX|Oxymesteronum [INN-Show More⌵

Canonical SMILES:  C[C@]12CCC(=O)C(O)=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O

Standard InChI:  InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

Standard InChI Key:  RXXBBHGCAXVBES-XMUHMHRVSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  1  0  0  0  0  0999 V2000
   -1.2458   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250    0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1958   -2.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417    3.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.8042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -0.9792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 11  1  0
  4  1  1  0
  5  2  2  0
  6  7  1  0
  7  4  1  0
  8  3  1  0
  9  2  1  0
 10 17  1  0
 11 13  1  0
 12  1  1  0
 13  4  1  0
 14  7  1  0
 15  6  1  0
 16 15  1  0
 17 12  1  0
 18 10  2  0
 19  5  1  0
  1 20  1  1
  8 21  1  1
  3 22  1  1
  8 23  1  6
  4 24  1  6
  7 25  1  1
  6 26  1  6
  5 10  1  0
  9 14  1  0
  6  3  1  0
  8 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908006

   OXYMESTERONE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 318.46

Molecular Weight (Monoisotopic): 318.2195

AlogP: 4.16

#Rotatable Bonds: ┄

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.12

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: 2.22

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names