(S)-2-amino-5-((R)-1-(carboxymethylamino)-1-oxo-3-(phenethylcarbamothioylthio)propan-2-ylamino)-5-oxopentanoic acid

ID: ALA3527413

PubChem CID: 101164969

Max Phase: Preclinical

Molecular Formula: C19H26N4O6S2

Molecular Weight: 470.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSC(=S)NCCc1ccccc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C19H26N4O6S2/c20-13(18(28)29)6-7-15(24)23-14(17(27)22-10-16(25)26)11-31-19(30)21-9-8-12-4-2-1-3-5-12/h1-5,13-14H,6-11,20H2,(H,21,30)(H,22,27)(H,23,24)(H,25,26)(H,28,29)/t13-,14-/m0/s1

Standard InChI Key:  WSGBVCNCZSZCGE-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   28.7722   -5.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4848   -5.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0594   -5.4143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4915   -5.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3466   -5.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2059   -5.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6314   -5.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4848   -4.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4915   -6.6647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2043   -5.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3466   -6.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6356   -6.6397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9103   -5.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9211   -5.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6339   -5.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7705   -5.4269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2043   -4.5973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0594   -7.0649    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.3483   -5.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7722   -6.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0604   -7.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3462   -8.3036    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.7756   -8.3019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7766   -9.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4918   -9.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4927  -10.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7785  -10.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7792  -11.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4949  -12.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2116  -11.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2073  -10.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  6
  4 10  1  0
  5  3  1  0
  6  2  1  0
  7 13  1  0
  8  2  2  0
  9  4  2  0
 10 14  1  0
 11  5  2  0
 12  7  2  0
 13  6  1  0
 14 15  1  0
 15  5  1  0
 16  4  1  0
 10 17  1  1
 18 20  1  0
 19  7  1  0
 20  1  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527413

   L-Gamma-Glutamyl-S-[(2-Phenylethyl)carbamothioyl]-L-Cysteinylglycine

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: 470.57

Molecular Weight (Monoisotopic): 470.1294

AlogP: -0.29

#Rotatable Bonds: 13

Polar Surface Area: 170.85

Molecular Species: ZWITTERION

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.79

CX Basic pKa: 9.31

CX LogP: -2.25

CX LogD: -5.68

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: 0.07

References

1. Yoshigae Y, Sridar C, Kent UM, Hollenberg PF..  (2013)  The inactivation of human CYP2E1 by phenethyl isothiocyanate, a naturally occurring chemopreventive agent, and its oxidative bioactivation.,  41  (4): [PMID:23371965] [10.1124/dmd.112.050609]

Source

Source(1):

• Scientific Literature