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

ID: ALA1836042

PubChem CID: 56682413

Max Phase: Preclinical

Molecular Formula: C24H41N3O6S2

Molecular Weight: 531.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H]1NC(=O)C[C@@H](/C=C/CCS)OC(=O)C[C@H](O)[C@@H]([C@@H](C)CC)NC(=O)[C@@H](CS)NC1=O

Standard InChI:  InChI=1S/C24H41N3O6S2/c1-4-6-10-17-23(31)26-18(14-35)24(32)27-22(15(3)5-2)19(28)13-21(30)33-16(9-7-8-11-34)12-20(29)25-17/h7,9,15-19,22,28,34-35H,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:  SOUWDYWQNTVVMP-RIRJJDMNSA-N

Molfile:  

     RDKit          2D

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    4.7193   -7.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524   -7.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212   -7.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1442   -5.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3829   -8.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713   -7.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -7.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2280   -6.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1584   -4.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5973   -5.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2090   -6.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9943   -6.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6059   -6.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4323   -7.6246    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695   -6.2360    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3515   -4.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -4.0580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
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  3 26  2  0
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  8 28  1  6
  1 14  1  0
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 29 30  2  0
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  2  3  1  0
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 35 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1836042

   (2S,6R,9S,12R,13S)-12-[(2S)-butan-2-yl]-6-butyl-13-hydroxy-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: 531.74

Molecular Weight (Monoisotopic): 531.2437

AlogP: 1.55

#Rotatable Bonds: 9

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 8

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: 1.94

CX LogD: 1.93

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.15

Np Likeness Score: 2.19

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