ID: ALA342892

Max Phase: Preclinical

Molecular Formula: C18H23IO2

Molecular Weight: 398.28

Molecule Type: Small molecule

Representations

Synonyms (1): 16alpha-iodo-17beta-Estradiol
Synonyms from Alternative Forms(1):

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

Standard InChI:  InChI=1S/C18H23IO2/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:  SSYGGPAGDDGXAF-ZXXIGWHRSA-N

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

Properties

Molecular Weight: 398.28

Molecular Weight (Monoisotopic): 398.0743

AlogP: 4.02

#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: 4.46

CX LogD: 4.46

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 2.05

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. Landvatter SW, Katzenellenbogen JA, McElvany KD, Welch MJ..  (1982)  (2R*,3S*)-1-[125I]Iodo-2,3-bis(4-hydroxyphenyl)pentane ([125I]iodonorhexestrol) and (2R*,3S*)-1-[77Br]Bromo-2,3-bis(4-hydroxyphenyl)pentane ([77Br]bromonorhexestrol), two gamma-emitting estrogens that show receptor-mediated uptake by target tissues in vivo.,  25  (11): [PMID:6292424] [10.1021/jm00353a007]

3. 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]

4. DaSilva JN, van Lier JE..  (1990)  Synthesis and structure-affinity of a series of 7 alpha-undecylestradiol derivatives: a potential vector for therapy and imaging of estrogen-receptor-positive cancers.,  33  (1): [PMID:2296033] [10.1021/jm00163a066]

Source

Source(1):

• Scientific Literature