(2S,6R,9S,12R,13S)-12-sec-butyl-13-hydroxy-2-((E)-4-mercaptobut-1-enyl)-9-(mercaptomethyl)-6-(3-(methylthio)propyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

ID: ALA1836144

Chembl Id: CHEMBL1836144

PubChem CID: 56602461

Max Phase: Preclinical

Molecular Formula: C23H39N3O6S3

Molecular Weight: 549.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H]1NC(=O)[C@@H](CS)NC(=O)[C@@H](CCSC)NC(=O)C[C@@H](/C=C/CCS)OC(=O)C[C@@H]1O

Standard InChI:  InChI=1S/C23H39N3O6S3/c1-4-14(2)21-18(27)12-20(29)32-15(7-5-6-9-33)11-19(28)24-16(8-10-35-3)22(30)25-17(13-34)23(31)26-21/h5,7,14-18,21,27,33-34H,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:  QPHJHMOKVYIJGF-DSRNDQRRSA-N

Alternative Forms

1. Parent:

   

   ALA1836144

   (2S,6R,9S,12R,13S)-12-[(2S)-butan-2-yl]-13-hydroxy-6-(2-methylsulfanylethyl)-2-[(E)-4-sulfanylbut-1-enyl]-9-(sulfanylmethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetrone

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: 549.78

Molecular Weight (Monoisotopic): 549.2001

AlogP: 1.11

#Rotatable Bonds: 9

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.73

CX Basic pKa:

CX LogP: 1.17

CX LogD: 1.17

Aromatic Rings: 0

Heavy Atoms: 35

QED Weighted: 0.14

Np Likeness Score: 2.00

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]

Source

Source(1):

• Scientific Literature