largazole thiol

ID: ALA1796689

Chembl Id: CHEMBL1796689

PubChem CID: 56663191

Max Phase: Preclinical

Molecular Formula: C21H28N4O4S3

Molecular Weight: 496.68

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Largazole Thiol | Largazole Thiol|CHEMBL1796689|BDBM50020912

Canonical SMILES:  CC(C)[C@H]1NC(=O)[C@]2(C)CSC(=N2)c2csc(n2)CNC(=O)C[C@@H](/C=C/CCS)OC1=O

Standard InChI:  InChI=1S/C21H28N4O4S3/c1-12(2)17-19(27)29-13(6-4-5-7-30)8-15(26)22-9-16-23-14(10-31-16)18-25-21(3,11-32-18)20(28)24-17/h4,6,10,12-13,17,30H,5,7-9,11H2,1-3H3,(H,22,26)(H,24,28)/b6-4+/t13-,17-,21+/m1/s1

Standard InChI Key:  VEDPEVJAYWVUSJ-FJNFOTEGSA-N

Alternative Forms

  1. Parent:

    ALA1796689

    LARGAZOLE THIOL

Associated Targets(Human)

HDAC1 Tclin Histone deacetylase (6747 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC1 Tclin Histone deacetylase 1 (10854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC3 Tclin Histone deacetylase 3 (3654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC2 Tclin Histone deacetylase 2 (3971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC8 Tclin Histone deacetylase 8 (4516 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
HDAC7 Tclin Histone deacetylase 7 (1047 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

Associated Targets(non-human)

Liver (8163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Serum (598 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: 496.68Molecular Weight (Monoisotopic): 496.1273AlogP: 2.34#Rotatable Bonds: 4
Polar Surface Area: 109.75Molecular Species: NEUTRALHBA: 9HBD: 3
#RO5 Violations: 0HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 9.99CX Basic pKa: 1.06CX LogP: 2.39CX LogD: 2.39
Aromatic Rings: 1Heavy Atoms: 32QED Weighted: 0.34Np Likeness Score: 1.76

References

1. Benelkebir H, Marie S, Hayden AL, Lyle J, Loadman PM, Crabb SJ, Packham G, Ganesan A..  (2011)  Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability.,  19  (12): [PMID:21420302] [10.1016/j.bmc.2011.02.024]
2. Chen F, Chai H, Su MB, Zhang YM, Li J, Xie X, Nan FJ..  (2014)  Potent and orally efficacious bisthiazole-based histone deacetylase inhibitors.,  (6): [PMID:24944733] [10.1021/ml400470s]
3. Kim B, Park H, Salvador LA, Serrano PE, Kwan JC, Zeller SL, Chen QY, Ryu S, Liu Y, Byeon S, Luesch H, Hong J..  (2014)  Evaluation of class I HDAC isoform selectivity of largazole analogues.,  24  (16): [PMID:25070421] [10.1016/j.bmcl.2014.07.006]
4. Salvador LA, Park H, Al-Awadhi FH, Liu Y, Kim B, Zeller SL, Chen QY, Hong J, Luesch H..  (2014)  Modulation of Activity Profiles for Largazole-Based HDAC Inhibitors through Alteration of Prodrug Properties.,  (8): [PMID:25147612] [10.1021/ml500170r]

Source