3-(4-(((3aR,8aS)-3a-hydroxy-8a-methyl-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1(2H)-yl)methyl)phenyl)acrylamide

ID: ALA3526396

Chembl Id: CHEMBL3526396

PubChem CID: 118753027

Max Phase: Preclinical

Molecular Formula: C21H23N3O2

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12Nc3ccccc3[C@]1(O)CCN2Cc1ccc(/C=C/C(N)=O)cc1

Standard InChI:  InChI=1S/C21H23N3O2/c1-20-21(26,17-4-2-3-5-18(17)23-20)12-13-24(20)14-16-8-6-15(7-9-16)10-11-19(22)25/h2-11,23,26H,12-14H2,1H3,(H2,22,25)/b11-10+/t20-,21+/m0/s1

Standard InChI Key:  GSUOTZHCHGUHCC-HRZVIGLNSA-N

Alternative Forms

1. Parent:

   

   ALA3526396

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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: 349.43

Molecular Weight (Monoisotopic): 349.1790

AlogP: 2.42

#Rotatable Bonds: 4

Polar Surface Area: 78.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: 6.96

CX LogP: 2.05

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: 0.46

References

1. Fredenhagen A, Kittelmann M, Oberer L, Kuhn A, Kühnöl J, Délémonté T, Aichholz R, Wang P, Atadja P, Shultz MD..  (2012)  Biocatalytic synthesis and structure elucidation of cyclized metabolites of the deacetylase inhibitor panobinostat (LBH589).,  40  (5): [PMID:22344701] [10.1124/dmd.111.043620]

Source

Source(1):

• Scientific Literature