(S)-2-amino-3-(3-((R)-3-((4-bromophenyl)hydroxycarbamoylthio)-1-(carboxymethylamino)-1-oxopropan-2-yl)ureido)propanoic acid

ID: ALA221011

Chembl Id: CHEMBL221011

PubChem CID: 16066818

Max Phase: Preclinical

Molecular Formula: C16H20BrN5O8S

Molecular Weight: 522.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CNC(=O)N[C@@H](CSC(=O)N(O)c1ccc(Br)cc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C16H20BrN5O8S/c17-8-1-3-9(4-2-8)22(30)16(29)31-7-11(13(25)19-6-12(23)24)21-15(28)20-5-10(18)14(26)27/h1-4,10-11,30H,5-7,18H2,(H,19,25)(H,23,24)(H,26,27)(H2,20,21,28)/t10-,11-/m0/s1

Standard InChI Key:  QDBJJGZTEVNDAF-QWRGUYRKSA-N

Alternative Forms

1. Parent:

   

   ALA221011

   (2S)-2-amino-3-[({[(1R)-1-[({[(4-bromophenyl)(hydroxy)amino]carbonyl}thio)methyl]-2-(carboxyamino)-2-oxoethyl]amino}carbonyl)amino]propanoic acid

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: 522.33

Molecular Weight (Monoisotopic): 521.0216

AlogP: -0.22

#Rotatable Bonds: 10

Polar Surface Area: 211.39

Molecular Species: ZWITTERION

HBA: 8

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.66

CX Basic pKa: 8.74

CX LogP: -3.29

CX LogD: -6.66

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.16

Np Likeness Score: -0.27

References

1. More SS, Vince R..  (2006)  A metabolically stable tight-binding transition-state inhibitor of glyoxalase-I.,  16  (23): [PMID:16997560] [10.1016/j.bmcl.2006.08.121]

2. More SS, Vince R..  (2009)  Inhibition of glyoxalase I: the first low-nanomolar tight-binding inhibitors.,  52  (15): [PMID:19610604] [10.1021/jm900382u]

Source

Source(1):

• Scientific Literature