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

ID: ALA3526822

PubChem CID: 118753165

Max Phase: Preclinical

Molecular Formula: C19H26N4O7S

Molecular Weight: 454.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H26N4O7S/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:  QHWHFUJECZNPGN-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    8.5306  -13.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2432  -12.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8180  -12.8896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2507  -13.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1053  -13.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9642  -13.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3894  -13.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2432  -12.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2507  -14.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9633  -12.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1053  -14.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3935  -14.1148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6684  -12.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801  -13.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928  -12.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298  -12.9022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9633  -12.0729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8180  -14.5399    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1062  -12.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5306  -14.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8190  -15.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1048  -15.7785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5341  -15.7767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5350  -16.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2501  -17.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511  -17.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370  -18.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5376  -19.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2533  -19.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9697  -19.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9656  -18.2455    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:

   

   ALA3526822

   ---

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: 454.51

Molecular Weight (Monoisotopic): 454.1522

AlogP: -0.45

#Rotatable Bonds: 13

Polar Surface Area: 187.92

Molecular Species: ZWITTERION

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.75

CX Basic pKa: 9.31

CX LogP: -3.19

CX LogD: -6.44

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: 0.20

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