2-Bromo-N-((S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ylmethyl)-acetamide

ID: ALA1628080

PubChem CID: 10025232

Max Phase: Preclinical

Molecular Formula: C21H28BrNO3

Molecular Weight: 422.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@]2(O)CNC(=O)CBr

Standard InChI:  InChI=1S/C21H28BrNO3/c1-20-8-6-16-15-5-3-14(24)10-13(15)2-4-17(16)18(20)7-9-21(20,26)12-23-19(25)11-22/h3,5,10,16-18,24,26H,2,4,6-9,11-12H2,1H3,(H,23,25)/t16-,17-,18+,20+,21-/m1/s1

Standard InChI Key:  VAUDLNNWQPHUCE-FJWRRNOESA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    9.8038   -5.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8050   -5.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0846   -6.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3574   -5.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541   -6.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5981   -4.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6552   -7.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0879   -4.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3562   -5.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5887   -6.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0858   -7.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9439   -5.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427   -5.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8253   -5.5129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3598   -7.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0817   -5.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9463   -7.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4156   -4.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0391   -4.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -7.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8582   -4.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2406   -6.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7969   -4.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8756   -6.1969    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.5271   -7.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0582   -6.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -6.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -5.4792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -6.7208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  9  1  0
  5  4  1  0
  6  1  1  0
  7  5  2  0
  8  1  1  0
  9  8  1  0
 10  2  1  0
 11  3  1  0
 12  5  1  0
 13 14  1  0
 14 18  1  0
 15 11  1  0
 16  6  1  0
 17  7  1  0
  6 18  1  6
 19 13  2  0
 20 22  1  0
 21  6  1  0
 22 12  2  0
  1 23  1  1
 24 26  1  0
 25 20  1  0
 26 13  1  0
 10 16  1  0
  3  4  1  0
  7 15  1  0
 17 20  2  0
  4 27  1  6
  3 28  1  1
  2 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628080

   2-bromo-N-[[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]methyl]acetamide

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: 422.36

Molecular Weight (Monoisotopic): 421.1253

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.33

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: 1.33

References

1. el Garrouj D, Aliau S, Aumelas A, Borgna JL..  (1995)  Steroidal affinity labels of the estrogen receptor. 2. 17 alpha-[(Haloacetamido)alkyl]estradiols.,  38  (13): [PMID:7608900] [10.1021/jm00013a011]

Source

Source(1):

• Scientific Literature