(E)-3-[1-(2-Dimethylaminoethyl)-2-hexyl-1H-benzimidazol-5-yl]-N-hydroxyacrylamide

ID: ALA1830424

Chembl Id: CHEMBL1830424

PubChem CID: 15983982

Max Phase: Preclinical

Molecular Formula: C20H30N4O2

Molecular Weight: 358.49

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(C)C

Standard InChI:  InChI=1S/C20H30N4O2/c1-4-5-6-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(2)3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+

Standard InChI Key:  PUFPSZILMLJFEU-ZRDIBKRKSA-N

Associated Targets(Human)

HDAC1 Tclin Histone deacetylase 1 (10854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780 (11979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC2 Tclin Histone deacetylase 2 (3971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC3 Tclin Histone deacetylase 3 (3654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC4 Tclin Histone deacetylase 4 (2328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC5 Tclin Histone deacetylase 5 (941 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC7 Tclin Histone deacetylase 7 (1047 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC8 Tclin Histone deacetylase 8 (4516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC9 Tclin Histone deacetylase 9 (708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC10 Tclin Histone deacetylase 10 (801 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC11 Tclin Histone deacetylase 11 (967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A1 Tchem Cytochrome P450 1A (45 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 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

Calculated Properties

Molecular Weight: 358.49Molecular Weight (Monoisotopic): 358.2369AlogP: 3.24#Rotatable Bonds: 10
Polar Surface Area: 70.39Molecular Species: BASEHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.68CX Basic pKa: 8.95CX LogP: 3.02CX LogD: 1.78
Aromatic Rings: 2Heavy Atoms: 26QED Weighted: 0.30Np Likeness Score: -0.97

References

1. Wang H, Yu N, Chen D, Lee KC, Lye PL, Chang JW, Deng W, Ng MC, Lu T, Khoo ML, Poulsen A, Sangthongpitag K, Wu X, Hu C, Goh KC, Wang X, Fang L, Goh KL, Khng HH, Goh SK, Yeo P, Liu X, Bonday Z, Wood JM, Dymock BW, Kantharaj E, Sun ET..  (2011)  Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile.,  54  (13): [PMID:21634430] [10.1021/jm2003552]

Source