ID: ALA2324360

Max Phase: Preclinical

Molecular Formula: C20H18FNO3S

Molecular Weight: 371.43

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COc1cccc(N(C)C(=O)c2ccc(-c3cccc(OC)c3F)s2)c1

Standard InChI:  InChI=1S/C20H18FNO3S/c1-22(13-6-4-7-14(12-13)24-2)20(23)18-11-10-17(26-18)15-8-5-9-16(25-3)19(15)21/h4-12H,1-3H3

Standard InChI Key:  XXGYSORRVIEKQF-UHFFFAOYSA-N

Associated Targets(Human)

MDA-MB-231 73002 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

11-beta-hydroxysteroid dehydrogenase 2 1168 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

11-beta-hydroxysteroid dehydrogenase 1 5910 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Aldo-keto-reductase family 1 member C3 1414 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Peroxisomal multifunctional enzyme type 2 123 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Estradiol 17-beta-dehydrogenase 2 1671 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Estradiol 17-beta-dehydrogenase 1 2224 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Estrogen receptor beta 9272 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Estrogen receptor alpha 17718 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Estradiol 17-beta-dehydrogenase 2 138 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Estradiol 17-beta-dehydrogenase 2 21 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 371.43Molecular Weight (Monoisotopic): 371.0991AlogP: 4.85#Rotatable Bonds: 5
Polar Surface Area: 38.77Molecular Species: NEUTRALHBA: 4HBD: 0
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: CX LogP: 4.31CX LogD: 4.31
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.64Np Likeness Score: -1.32

References

1. Marchais-Oberwinkler S, Xu K, Wetzel M, Perspicace E, Negri M, Meyer A, Odermatt A, Möller G, Adamski J, Hartmann RW..  (2013)  Structural optimization of 2,5-thiophene amides as highly potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors for the treatment of osteoporosis.,  56  (1): [PMID:23145773] [10.1021/jm3014053]
2. Gargano EM, Perspicace E, Hanke N, Carotti A, Marchais-Oberwinkler S, Hartmann RW..  (2014)  Metabolic stability optimization and metabolite identification of 2,5-thiophene amide 17β-hydroxysteroid dehydrogenase type 2 inhibitors.,  87  [PMID:25259513] [10.1016/j.ejmech.2014.09.061]

Source