Thailandepsin A

ID: ALA1836142

Cas Number: 1278522-67-0

PubChem CID: 56602459

Max Phase: Preclinical

Molecular Formula: C23H37N3O6S3

Molecular Weight: 547.77

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Thailandepsin A | Thailandepsin A|CHEMBL1836142|BDBM50354088|1278522-67-0

Canonical SMILES:  CC[C@H](C)[C@H]1NC(=O)[C@H]2CSSCC/C=C/[C@H](CC(=O)N[C@H](CCSC)C(=O)N2)OC(=O)C[C@@H]1O

Standard InChI:  InChI=1S/C23H37N3O6S3/c1-4-14(2)21-18(27)12-20(29)32-15-7-5-6-9-34-35-13-17(23(31)26-21)25-22(30)16(8-10-33-3)24-19(28)11-15/h5,7,14-18,21,27H,4,6,8-13H2,1-3H3,(H,24,28)(H,25,30)(H,26,31)/b7-5+/t14-,15+,16+,17+,18-,21+/m0/s1

Standard InChI Key:  VJXBYUITQBTTQM-DSRNDQRRSA-N

Molfile:  

     RDKit          2D

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  8 37  1  1
  1 38  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1836142

   THAILANDEPSIN A

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: 547.77

Molecular Weight (Monoisotopic): 547.1844

AlogP: 1.65

#Rotatable Bonds: 5

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.87

CX Basic pKa: ┄

CX LogP: 0.94

CX LogD: 0.93

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: 2.23

References

1. Wang C, Henkes LM, Doughty LB, He M, Wang D, Meyer-Almes FJ, Cheng YQ..  (2011)  Thailandepsins: bacterial products with potent histone deacetylase inhibitory activities and broad-spectrum antiproliferative activities.,  74  (10): [PMID:21793558] [10.1021/np200324x]

2. Fukui Y, Narita K, Dan S, Yamori T, Ito A, Yoshida M, Katoh T..  (2014)  Total synthesis of burkholdacs A and B and 5,6,20-tri-epi-burkholdac A: HDAC inhibition and antiproliferative activity.,  76  [PMID:24589486] [10.1016/j.ejmech.2014.02.044]

3. Wang C, Flemming CJ, Cheng YQ..  (2012)  Discovery and activity profiling of thailandepsins A through F, potent histone deacetylase inhibitors, from Burkholderia thailandensis E264.,  3  (8): [PMID:23997923] [10.1039/c2md20024d]

Source

Source(1):

• Scientific Literature