11-ketoestrone

ID: ALA489926

Cas Number: 7533-97-3

PubChem CID: 193437

Max Phase: Preclinical

Molecular Formula: C18H20O3

Molecular Weight: 284.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 11-Ketoestrone | 7533-97-3|11-ketoestrone|3-hydroxyestra-1(10),2,4-triene-11,17-dione|CHEMBL489926|SCHEMBL17184300|3-Hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione|DTXSID00996777|Estra-1,3,5(10)-triene-11,17-dione, 3-hydroxy-, (9 beta)-

Canonical SMILES:  C[C@]12CC(=O)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O

Standard InChI:  InChI=1S/C18H20O3/c1-18-9-15(20)17-12-5-3-11(19)8-10(12)2-4-13(17)14(18)6-7-16(18)21/h3,5,8,13-14,17,19H,2,4,6-7,9H2,1H3/t13-,14-,17+,18-/m0/s1

Standard InChI Key:  WKUQOYYYFVBROI-ZZCKCESHSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    3.8322  -15.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8310  -16.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426  -16.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5406  -15.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2575  -15.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2567  -16.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689  -16.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6866  -16.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707  -15.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6839  -15.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6943  -13.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9728  -14.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4076  -14.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3998  -15.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1819  -15.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6732  -14.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1946  -14.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619  -13.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4024  -13.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4563  -13.2707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1172  -16.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9657  -15.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931  -15.9438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6749  -14.7040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
  2  3  2  0
  3  6  1  0
  1  2  1  0
  5  9  1  0
  6  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 12 18  2  0
  7  8  1  0
  8 10  1  0
 13 19  1  1
  9 10  1  0
 17 20  2  0
  5  4  1  0
  2 21  1  0
  4  1  2  0
  9 22  1  6
  5  6  2  0
 14 23  1  6
 10 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA489926

   3-Hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione

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: 284.36

Molecular Weight (Monoisotopic): 284.1412

AlogP: 3.00

#Rotatable Bonds: ┄

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.59

CX Basic pKa: ┄

CX LogP: 3.39

CX LogD: 3.38

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: 1.97

References

1. Podust LM, von Kries JP, Eddine AN, Kim Y, Yermalitskaya LV, Kuehne R, Ouellet H, Warrier T, Alteköster M, Lee JS, Rademann J, Oschkinat H, Kaufmann SH, Waterman MR..  (2007)  Small-molecule scaffolds for CYP51 inhibitors identified by high-throughput screening and defined by X-ray crystallography.,  51  (11): [PMID:17846131] [10.1128/aac.00311-07]

Source

Source(1):

• Scientific Literature