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

ID: ALA2068753

PubChem CID: 70684529

Max Phase: Preclinical

Molecular Formula: C23H31NO5

Molecular Weight: 401.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1CC[C@H]2[C@H]3[C@@H](c4ccc(OC(C)=O)cc4C[C@H]3C)[C@@H](O[N+](=O)[O-])C[C@]12C

Standard InChI:  InChI=1S/C23H31NO5/c1-5-16-6-9-19-21-13(2)10-15-11-17(28-14(3)25)7-8-18(15)22(21)20(29-24(26)27)12-23(16,19)4/h7-8,11,13,16,19-22H,5-6,9-10,12H2,1-4H3/t13-,16+,19+,20+,21+,22+,23-/m1/s1

Standard InChI Key:  LDRROAVROYACBW-WMYFERIHSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    8.3567   -5.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0630   -6.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7800   -5.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7832   -5.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3534   -5.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6438   -3.8194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6365   -6.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6397   -7.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0737   -4.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0777   -7.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6471   -4.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3633   -7.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5578   -6.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9301   -5.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3640   -3.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9374   -3.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5697   -4.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9367   -7.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -7.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2304   -7.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -7.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0478   -5.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8005   -6.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2271   -6.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7767   -4.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898   -7.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008   -7.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5492   -3.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2636   -3.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3889   -4.8127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3514   -6.7045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0627   -5.4692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7739   -6.7085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  1  0
  4  2  1  0
  5  1  1  0
  6 11  1  0
  7  1  1  0
  8  7  2  0
  9  5  1  0
 10  2  1  0
  5 11  1  1
 12  8  1  0
 13  4  1  0
 14  7  1  0
 15  6  1  0
 16  6  2  0
 17  3  1  0
 18  8  1  0
 19 21  1  0
 20 24  1  0
 21 20  1  0
 22 13  1  0
 23 19  2  0
 24 14  2  0
  3 25  1  1
 10 26  1  6
 27 19  1  0
 17 28  1  1
 29 28  1  0
 17 30  1  6
  4  3  1  0
 12 10  1  0
 20 18  2  0
 17 22  1  0
  2  1  1  0
  1 31  1  6
  2 32  1  1
  4 33  1  6
M  CHG  2   6   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2068753

   [(7R,8S,9S,11S,13R,14S,17S)-17-ethyl-7,13-dimethyl-11-nitrooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[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: 401.50

Molecular Weight (Monoisotopic): 401.2202

AlogP: 4.93

#Rotatable Bonds: 4

Polar Surface Area: 78.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.30

CX LogD: 5.30

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: 1.35

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