13-Bromo-5-methoxy-15-methyl-(13S)-tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-one

ID: ALA2068060

PubChem CID: 21723393

Max Phase: Preclinical

Molecular Formula: C19H23BrO2

Molecular Weight: 363.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](Br)C[C@@H]12

Standard InChI:  InChI=1S/C19H23BrO2/c1-19-8-7-14-13-6-4-12(22-2)9-11(13)3-5-15(14)16(19)10-17(20)18(19)21/h4,6,9,14-17H,3,5,7-8,10H2,1-2H3/t14-,15-,16+,17+,19+/m1/s1

Standard InChI Key:  CSELWEPNDJXTQB-GJGATLCTSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    9.7990   -5.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8020   -5.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0800   -6.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5839   -4.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3674   -5.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579   -6.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5765   -6.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0688   -5.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6610   -7.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0863   -4.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726   -5.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0914   -7.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453   -5.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3736   -7.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8430   -4.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9515   -7.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8921   -5.4885    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.2389   -7.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7959   -4.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2358   -6.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -7.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324   -8.3690    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
  4  1  1  0
  5 11  1  0
  6  5  1  0
  7  2  1  0
  8  4  1  0
  9  6  2  0
 10  1  1  0
 11 10  1  0
 12  3  1  0
 13  6  1  0
 14 12  1  0
 15  4  2  0
 16  9  1  0
  8 17  1  1
 18 20  1  0
  1 19  1  1
 20 13  2  0
 21 18  1  0
 22 21  1  0
  8  7  1  0
  5  3  1  0
 14  9  1  0
 16 18  2  0
  2  1  1  0
  3  2  1  0
  5 23  1  6
  3 24  1  1
  2 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2068060

   (8R,9S,13S,14S,16S)-16-bromo-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

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: 363.30

Molecular Weight (Monoisotopic): 362.0881

AlogP: 4.49

#Rotatable Bonds: 1

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.12

CX LogD: 5.12

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: 1.52

References

1. Heiman DF, Senderoff SG, Katzenellenbogen JA, Neeley RJ..  (1980)  Estrogen receptor based imaging agents. 1. Synthesis and receptor binding affinity of some aromatic and D-ring halogenated estrogens.,  23  (9): [PMID:7411555] [10.1021/jm00183a007]

Source

Source(1):

• Scientific Literature