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

ID: ALA1628064

Chembl Id: CHEMBL1628064

Cas Number: 15833-07-5

PubChem CID: 14607641

Max Phase: Preclinical

Molecular Formula: C18H23BrO2

Molecular Weight: 351.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4cc(Br)c(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C18H23BrO2/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-16(20)15(19)9-13(10)11/h8-9,11-12,14,17,20-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

Standard InChI Key:  SORISAYAZBCIQH-XSSYPUMDSA-N

Alternative Forms

1. Parent:

   

   ALA1628064

   2-Bromoestradiol

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: 8.48

CX Basic pKa: ┄

CX LogP: 4.51

CX LogD: 4.48

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 2.07

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. Yadav MR, Barmade MA, Tamboli RS, Murumkar PR..  (2015)  Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer.,  105  [PMID:26469743] [10.1016/j.ejmech.2015.09.038]

4. 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]

5. Adhikari N, Baidya SK, Jha T..  (2020)  Effective anti-aromatase therapy to battle against estrogen-mediated breast cancer: Comparative SAR/QSAR assessment on steroidal aromatase inhibitors.,  208  [PMID:33017749] [10.1016/j.ejmech.2020.112845]

Source

Source(1):

• Scientific Literature