rac-(1R,5R,6R)-3-Hexyl-6-hydroxy-2-phenyl-1-(phenylvinyl)-bicyclo[3.3.0]oct-2-ene

ID: ALA1765959

Chembl Id: CHEMBL1765959

PubChem CID: 52936713

Max Phase: Preclinical

Molecular Formula: C28H34O

Molecular Weight: 386.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(c1ccccc1)[C@@]12CC[C@@H](O)[C@@H]1CC(CCCCCC)=C2c1ccccc1

Standard InChI:  InChI=1S/C28H34O/c1-3-4-5-8-17-24-20-25-26(29)18-19-28(25,21(2)22-13-9-6-10-14-22)27(24)23-15-11-7-12-16-23/h6-7,9-16,25-26,29H,2-5,8,17-20H2,1H3/t25-,26+,28-/m0/s1

Standard InChI Key:  ZFXMYHPLTQTTFW-REUBFRLUSA-N

Alternative Forms

1. Parent:

   

   ALA1765959

   (1r,3ar,6ar)-5-Hexyl-4-Phenyl-3a-(1-Phenylethenyl)-1,2,3,3a,6,6a-Hexahydropentalen-1-Ol

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

Calculated Properties

Molecular Weight: 386.58

Molecular Weight (Monoisotopic): 386.2610

AlogP: 7.29

#Rotatable Bonds: 8

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.05

CX LogD: 7.05

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 1.01

References

1. Whitby RJ, Stec J, Blind RD, Dixon S, Leesnitzer LM, Orband-Miller LA, Williams SP, Willson TM, Xu R, Zuercher WJ, Cai F, Ingraham HA..  (2011)  Small molecule agonists of the orphan nuclear receptors steroidogenic factor-1 (SF-1, NR5A1) and liver receptor homologue-1 (LRH-1, NR5A2).,  54  (7): [PMID:21391689] [10.1021/jm1014296]

2. Flynn AR, Mays SG, Ortlund EA, Jui NT..  (2018)  Development of Hybrid Phospholipid Mimics as Effective Agonists for Liver Receptor Homologue-1.,  9  (10): [PMID:30344916] [10.1021/acsmedchemlett.8b00361]

3. Mays SG, Flynn AR, Cornelison JL, Okafor CD, Wang H, Wang G, Huang X, Donaldson HN, Millings EJ, Polavarapu R, Moore DD, Calvert JW, Jui NT, Ortlund EA..  (2019)  Development of the First Low Nanomolar Liver Receptor Homolog-1 Agonist through Structure-guided Design.,  62  (24): [PMID:31419141] [10.1021/acs.jmedchem.9b00753]

4. D'Agostino EH, Flynn AR, Cornelison JL, Mays SG, Patel A, Jui NT, Ortlund EA..  (2020)  Development of a Versatile and Sensitive Direct Ligand Binding Assay for Human NR5A Nuclear Receptors.,  11  (3): [PMID:32184971] [10.1021/acsmedchemlett.9b00442]

5. Lang A, Isigkeit L, Schubert-Zsilavecz M, Merk D..  (2021)  The Medicinal Chemistry and Therapeutic Potential of LRH-1 Modulators.,  64  (23.0): [PMID:34839661] [10.1021/acs.jmedchem.1c01663]

6. Lang A, Isigkeit L, Schubert-Zsilavecz M, Merk D..  (2021)  The Medicinal Chemistry and Therapeutic Potential of LRH-1 Modulators.,  64  (23.0): [PMID:34839661] [10.1021/acs.jmedchem.1c01663]

Source

Source(1):

• Scientific Literature