Thailandepsin B

ID: ALA1836145

PubChem CID: 56676500

Max Phase: Preclinical

Molecular Formula: C24H39N3O6S2

Molecular Weight: 529.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Thailandepsin B | CHEMBL1836145|Thailandepsin B|BDBM50354084

Canonical SMILES:  CCCC[C@H]1NC(=O)C[C@H]2/C=C/CCSSC[C@@H](NC1=O)C(=O)N[C@H]([C@@H](C)CC)[C@@H](O)CC(=O)O2

Standard InChI:  InChI=1S/C24H39N3O6S2/c1-4-6-10-17-23(31)26-18-14-35-34-11-8-7-9-16(12-20(29)25-17)33-21(30)13-19(28)22(15(3)5-2)27-24(18)32/h7,9,15-19,22,28H,4-6,8,10-14H2,1-3H3,(H,25,29)(H,26,31)(H,27,32)/b9-7+/t15-,16+,17+,18+,19-,22+/m0/s1

Standard InChI Key:  MUNWAZFRKGVMPQ-RIRJJDMNSA-N

Molfile:  

     RDKit          2D

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    5.2860   -6.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191   -6.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879   -6.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3032  -10.0662    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0158   -3.0397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 20  2  0
  3  4  1  0
  6 21  2  0
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  3 26  2  0
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  2  3  1  0
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 34 33  1  0
  8 37  1  1
  1 38  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1836145

   THAILANDEPSIN B

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: 529.73

Molecular Weight (Monoisotopic): 529.2280

AlogP: 2.08

#Rotatable Bonds: 5

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.93

CX Basic pKa: ┄

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.24

Np Likeness Score: 2.41

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. 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