(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

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

Molfile:  

     RDKit          2D

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    6.4667   -8.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6277   -8.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3608   -9.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -9.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620   -8.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -8.5884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -7.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0526   -7.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9578   -7.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7539   -7.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2913  -10.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797   -9.3986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1364   -7.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -6.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885   -7.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5057   -7.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1174   -8.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9027   -7.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5143   -8.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3407   -9.2121    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779   -7.8235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599   -6.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5454   -5.6455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0547   -9.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
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  7  8  1  0
 11 12  1  0
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  3 25  2  0
 13 14  1  0
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 11 34  1  0
  8 27  1  6
  1 14  1  0
  1 28  1  6
 28 29  2  0
 11 15  1  6
 29 30  1  0
  1  2  1  0
 30 31  1  0
 34 16  1  0
 31 32  1  0
  2  3  1  0
 27 33  1  0
 34 35  1  1
 24 36  1  0
M  END

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: ┄

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