(1R,5R,3''R,4''S,5''S)-5''-(2''-Oxo-hexahydro-thieno[3,4-d]imidazol-4''-yl)pentanoc acid [12'-(4-hydroxy-4-methyl-2-oxo-6-oxa-3-aza-bicyclo[3.1.0]hex-1-yl)-12'-oxododecyl]amide

ID: ALA514331

PubChem CID: 44585360

Max Phase: Preclinical

Molecular Formula: C27H44N4O6S

Molecular Weight: 552.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(O)NC(=O)[C@@]2(C(=O)CCCCCCCCCCCNC(=O)CCCC[C@@H]3SC[C@@H]4NC(=O)N[C@@H]43)O[C@@H]12

Standard InChI:  InChI=1S/C27H44N4O6S/c1-26(36)23-27(37-23,24(34)31-26)20(32)14-9-7-5-3-2-4-6-8-12-16-28-21(33)15-11-10-13-19-22-18(17-38-19)29-25(35)30-22/h18-19,22-23,36H,2-17H2,1H3,(H,28,33)(H,31,34)(H2,29,30,35)/t18-,19-,22-,23-,26?,27-/m0/s1

Standard InChI Key:  FGYILHWEYDHGNQ-QGPPHQKNSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.9362  -10.5431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625  -10.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5950  -10.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -9.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -9.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9138   -8.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -8.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -8.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -9.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0343   -8.8262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3876   -9.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391  -10.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813  -10.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -8.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3487   -9.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640   -8.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -9.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -8.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -9.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219   -8.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6355   -9.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3508   -8.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0645   -9.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7798   -8.8795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4934   -9.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4918  -10.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2087   -8.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224   -9.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6376   -8.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3513   -9.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0664   -8.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7204   -9.3843    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3977   -8.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3342   -8.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1583   -8.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -7.3411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7678   -6.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0929   -7.3185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5083   -8.1042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9792   -8.1167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7817   -6.0205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
  6  5  1  0
 20 21  1  0
  4 10  1  1
 21 22  1  0
  4  6  1  0
 22 23  1  0
  3 11  1  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
  3 12  1  0
 25 26  2  0
 25 27  1  0
  2 13  2  0
 27 28  1  0
  2  5  1  0
 28 29  1  0
  9 14  1  0
 29 30  1  0
  4  3  1  0
 31 30  1  1
 31 32  1  0
 14 15  1  0
  5  7  1  1
 32 33  1  0
 33 35  1  0
 34 31  1  0
 34 35  1  0
 15 16  1  0
  3  1  1  0
 16 17  1  0
  7  8  2  0
 17 18  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 34  1  0
  5  4  1  0
 34 39  1  6
 18 19  1  0
 35 40  1  6
  7  9  1  0
 37 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA514331

   5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[12-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-12-oxododecyl]pentanamide

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: 552.74

Molecular Weight (Monoisotopic): 552.2982

AlogP: 2.27

#Rotatable Bonds: 18

Polar Surface Area: 149.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.29

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.08

Np Likeness Score: 0.23

References

1. Kuramochi K, Yukizawa S, Ikeda S, Sunoki T, Arai S, Matsui R, Morita A, Mizushina Y, Sakaguchi K, Sugawara F, Ikekita M, Kobayashi S..  (2008)  Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation.,  16  (9): [PMID:18375133] [10.1016/j.bmc.2008.03.029]

2. Yoda T, Furuta M, Tsutsumi T, Ikeda S, Yukizawa S, Arai S, Morita A, Yamatoya K, Nakata K, Tomoshige S, Ohgane K, Furuyama Y, Sakaguchi K, Sugawara F, Kobayashi S, Ikekita M, Kuramochi K..  (2021)  Epo-C12 inhibits peroxiredoxin 1 peroxidase activity.,  41  [PMID:34015702] [10.1016/j.bmc.2021.116203]

Source

Source(1):

• Scientific Literature