13-bromo-15-methyl-(13S,14R)-tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,14-diol

ID: ALA2068059

PubChem CID: 13344601

Max Phase: Preclinical

Molecular Formula: C18H23BrO2

Molecular Weight: 351.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H23BrO2/c1-18-7-6-13-12-5-3-11(20)8-10(12)2-4-14(13)15(18)9-16(19)17(18)21/h3,5,8,13-17,20-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1

Standard InChI Key:  ICCJJRSEGGYXMX-ZMSHIADSSA-N

Molfile:  

     RDKit          2D

 24 27  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
    9.8021   -5.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0801   -6.3057    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
    7.6578   -6.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5840   -4.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5765   -6.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609   -7.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0689   -5.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0863   -4.6506    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
    6.9452   -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
    6.9514   -7.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8923   -5.4885    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -7.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8431   -4.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357   -6.3164    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
    5.5292   -7.5458    0.0000 O   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 11  1  0
  5  4  1  0
  6  1  1  0
  7  2  1  0
  8  5  2  0
  9  6  1  0
 10  1  1  0
 11 10  1  0
 12  3  1  0
 13  5  1  0
 14 12  1  0
 15  8  1  0
  9 16  1  1
 17 19  1  0
  6 18  1  1
 19 13  2  0
  1 20  1  1
 21 17  1  0
  9  7  1  0
  4  3  1  0
 14  8  1  0
 17 15  2  0
  2  1  1  0
  3  2  1  0
  4 22  1  6
  3 23  1  1
  2 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2068059

   (8R,9S,13S,14S,16S,17R)-16-bromo-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

Molecule Features

Natural Product: Yes

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: 351.28

Molecular Weight (Monoisotopic): 350.0881

AlogP: 3.98

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.33

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 2.08

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