Acetic acid 3-acetoxy-17-ethynyl-9-hydroxy-13-methyl-11-nitrooxy-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester

ID: ALA2068752

PubChem CID: 70686657

Max Phase: Preclinical

Molecular Formula: C24H27NO7

Molecular Weight: 441.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CCc4cc(OC(C)=O)ccc4[C@H]3[C@@H](O[N+](=O)[O-])C[C@@]21C

Standard InChI:  InChI=1S/C24H27NO7/c1-5-24(31-15(3)27)11-10-20-19-8-6-16-12-17(30-14(2)26)7-9-18(16)22(19)21(32-25(28)29)13-23(20,24)4/h1,7,9,12,19-22H,6,8,10-11,13H2,2-4H3/t19-,20-,21-,22+,23-,24-/m0/s1

Standard InChI Key:  WBWZXPKLNQUKMC-WMGXJHCHSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
    8.3808   -5.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8095   -5.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0890   -6.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898   -5.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6793   -3.8340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6019   -4.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8120   -5.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6751   -6.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1013   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6703   -4.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4238   -4.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6775   -7.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5995   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1087   -7.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5886   -6.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2399   -4.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3908   -3.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612   -5.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3052   -3.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9597   -3.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0866   -5.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -7.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9661   -7.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857   -7.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2465   -7.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -7.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0133   -3.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8244   -6.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -6.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8071   -4.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2856   -2.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097   -7.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3798   -6.7272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0934   -5.4878    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070   -6.7313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  4  1  1  0
  5 10  1  0
  6  2  1  0
  7  3  1  0
  8  1  1  0
  9  4  1  0
  4 10  1  1
  6 11  1  6
 12  8  2  0
  6 13  1  1
 14  3  1  0
 15  7  1  0
 16 11  3  0
 17  5  1  0
 18  8  1  0
 19 13  1  0
 20  5  2  0
 21 15  1  0
 22 26  1  0
 23 12  1  0
 24 12  1  0
 25 29  1  0
 26 25  1  0
 27 19  2  0
 28 22  2  0
 29 18  2  0
  2 30  1  1
 31 19  1  0
 32 22  1  0
  7  2  1  0
 14 24  1  0
 25 23  2  0
  6 21  1  0
  2  9  1  0
  1 33  1  6
  3 34  1  1
  7 35  1  6
M  CHG  2   5   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2068752

   [(8S,9S,11S,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-11-nitrooxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate

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: 441.48

Molecular Weight (Monoisotopic): 441.1788

AlogP: 3.59

#Rotatable Bonds: 4

Polar Surface Area: 104.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: 1.06

References

1. Peters RH, Crowe DF, Avery MA, Chong WK, Tanabe M..  (1989)  11 beta-nitrate estrane analogues: potent estrogens.,  32  (10): [PMID:2795603] [10.1021/jm00130a014]

Source

Source(1):

• Scientific Literature