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

ID: ALA2067988

Cas Number: 1630-83-7

PubChem CID: 14334330

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)c(Br)c4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C18H23BrO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h4,6,11-12,14,16,20-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

Standard InChI Key:  WSJCDIBESNMSPH-ZHIYBZGJSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
    9.8026   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6605   -6.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8013   -5.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6592   -7.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3704   -5.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0831   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9494   -7.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898   -4.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3761   -7.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3675   -5.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0860   -7.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436   -5.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5800   -6.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5879   -4.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2367   -7.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338   -6.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0644   -5.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440   -8.3728    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.7955   -4.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -7.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8430   -4.0374    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  2  2  0
  5 10  1  0
  6  3  1  0
  7  4  1  0
  8  1  1  0
  9 11  1  0
 10  8  1  0
 11  6  1  0
 12  2  1  0
 13  3  1  0
 14  1  1  0
 15 16  1  0
 16 12  2  0
 17 14  1  0
 18  7  1  0
  1 19  1  1
 20 15  1  0
 14 21  1  1
 17 13  1  0
  5  6  1  0
  9  4  1  0
 15  7  2  0
  2  5  1  0
  3  1  1  0
  5 22  1  6
  6 23  1  1
  3 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2067988

   Estra-1,3,5(10)-triene-3,17-diol, 4-bromo-, (17beta)-

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: 4.37

#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: 8.50

CX Basic pKa: ┄

CX LogP: 4.51

CX LogD: 4.48

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 1.96

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]

2. Gantchev TG, Ali H, van Lier JE..  (1994)  Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives.,  37  (24): [PMID:7990116] [10.1021/jm00050a013]

3. Poirier D, Roy J, Cortés-Benítez F, Dutour R..  (2016)  Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.,  26  (21): [PMID:27687674] [10.1016/j.bmcl.2016.09.046]

Source

Source(1):

• Scientific Literature