ID: ALA1627367

Max Phase: Approved

First Approval: 2020

Molecular Formula: C18H23FO2

Molecular Weight: 290.38

Molecule Type: Small molecule

Representations

Synonyms (3): 16.alpha.-fluoroestradiol | Fluoroestradiol | Fluoroestradiol, 16.alpha.-
Synonyms from Alternative Forms(3):

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

Standard InChI:  InChI=1S/C18H23FO2/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:  KDLLNMRYZGUVMA-ZXXIGWHRSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 290.38

Molecular Weight (Monoisotopic): 290.1682

AlogP: 3.56

#Rotatable Bonds: 0

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.33

CX Basic pKa:

CX LogP: 3.56

CX LogD: 3.56

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: 1.91

References

1. Levesque C, Merand Y, Dufour JM, Labrie C, Labrie F..  (1991)  Synthesis and biological activity of new halo-steroidal antiestrogens.,  34  (5): [PMID:2033587] [10.1021/jm00109a014]

2. Liu A, Carlson KE, Katzenellenbogen JA..  (1992)  Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography.,  35  (11): [PMID:1597861] [10.1021/jm00089a024]

3. Pomper MG, VanBrocklin H, Thieme AM, Thomas RD, Kiesewetter DO, Carlson KE, Mathias CJ, Welch MJ, Katzenellenbogen JA..  (1990)  11 beta-methoxy-, 11 beta-ethyl- and 17 alpha-ethynyl-substituted 16 alpha-fluoroestradiols: receptor-based imaging agents with enhanced uptake efficiency and selectivity.,  33  (12): [PMID:1701833] [10.1021/jm00174a009]

4. Hanson RN, Napolitano E, Fiaschi R..  (1990)  Synthesis and estrogen receptor binding of novel 11 beta-substituted estra-1,3,5(10)-triene-3,17 beta-diols.,  33  (12): [PMID:2258901] [10.1021/jm00174a010]

5. Yoo J, Dence CS, Sharp TL, Katzenellenbogen JA, Welch MJ..  (2005)  Synthesis of an estrogen receptor beta-selective radioligand: 5-[18F]fluoro-(2R,3S)-2,3-bis(4-hydroxyphenyl)pentanenitrile and comparison of in vivo distribution with 16alpha-[18F]fluoro-17beta-estradiol.,  48  (20): [PMID:16190762] [10.1021/jm050121f]

6. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates