2-Chloro-4-((3S,3aS,4S)-4-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile

ID: ALA3326454

Chembl Id: CHEMBL3326454

Cas Number: 1421375-26-9

PubChem CID: 71239417

Max Phase: Preclinical

Molecular Formula: C15H16ClN3O2

Molecular Weight: 305.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1C(c2ccc(C#N)c(Cl)c2C)=NN2CC[C@H](O)[C@@H]12

Standard InChI:  InChI=1S/C15H16ClN3O2/c1-8-10(4-3-9(7-17)12(8)16)13-15(21-2)14-11(20)5-6-19(14)18-13/h3-4,11,14-15,20H,5-6H2,1-2H3/t11-,14-,15+/m0/s1

Standard InChI Key:  RJZJEPYCJHLWQR-TUKIKUTGSA-N

Alternative Forms

1. Parent:

   

   ALA3326454

   2-Chloro-4-[(3s,3as,4s)-4-Hydroxy-3-Methoxy-3a,4,5,6-Tetrahydro-3h-Pyrrolo[1,2-B]pyrazol-2-Yl]-3-Methylbenzonitrile

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: 305.76

Molecular Weight (Monoisotopic): 305.0931

AlogP: 1.69

#Rotatable Bonds: 2

Polar Surface Area: 68.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.87

CX LogP: 1.57

CX LogD: 1.57

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.90

Np Likeness Score: 0.13

References

1. Ullrich T, Sasmal S, Boorgu V, Pasagadi S, Cheera S, Rajagopalan S, Bhumireddy A, Shashikumar D, Chelur S, Belliappa C, Pandit C, Krishnamurthy N, Mukherjee S, Ramanathan A, Ghadiyaram C, Ramachandra M, Santos PG, Lagu B, Bock MG, Perrone MH, Weiler S, Keller H..  (2014)  3-alkoxy-pyrrolo[1,2-b]pyrazolines as selective androgen receptor modulators with ideal physicochemical properties for transdermal administration.,  57  (17): [PMID:25121964] [10.1021/jm5009049]

2. Xiang W, Wang S..  (2022)  Therapeutic Strategies to Target the Androgen Receptor.,  65  (13.0): [PMID:35786895] [10.1021/acs.jmedchem.2c00716]

Source

Source(1):

• Scientific Literature