(2S,3S)-2-((S)-2-((S)-2-((S)-2-amino-3-carboxypropanamido)-3-phenylpropanamido)-3-hydroxypropanamido)-3-methylpentanoic acid

ID: ALA2325118

Chembl Id: CHEMBL2325118

PubChem CID: 16122630

Max Phase: Preclinical

Molecular Formula: C22H32N4O8

Molecular Weight: 480.52

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C22H32N4O8/c1-3-12(2)18(22(33)34)26-21(32)16(11-27)25-20(31)15(9-13-7-5-4-6-8-13)24-19(30)14(23)10-17(28)29/h4-8,12,14-16,18,27H,3,9-11,23H2,1-2H3,(H,24,30)(H,25,31)(H,26,32)(H,28,29)(H,33,34)/t12-,14-,15-,16-,18-/m0/s1

Standard InChI Key:  OYZFXMLOPVDLIH-XEQYVGRISA-N

Alternative Forms

1. Parent:

   

   ALA2325118

   H-Asp-Phe-Ser-Ile-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 480.52

Molecular Weight (Monoisotopic): 480.2220

AlogP: -1.39

#Rotatable Bonds: 14

Polar Surface Area: 208.15

Molecular Species: ACID

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.52

CX Basic pKa: 8.23

CX LogP: -3.57

CX LogD: -6.46

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.17

Np Likeness Score: 0.32

References

1. Jean Kumar VU, Poyraz Ö, Saxena S, Schnell R, Yogeeswari P, Schneider G, Sriram D..  (2013)  Discovery of novel inhibitors targeting the Mycobacterium tuberculosis O-acetylserine sulfhydrylase (CysK1) using virtual high-throughput screening.,  23  (5): [PMID:23391589] [10.1016/j.bmcl.2013.01.031]

2. Poyraz O, Jeankumar VU, Saxena S, Schnell R, Haraldsson M, Yogeeswari P, Sriram D, Schneider G..  (2013)  Structure-guided design of novel thiazolidine inhibitors of O-acetyl serine sulfhydrylase from Mycobacterium tuberculosis.,  56  (16): [PMID:23879381] [10.1021/jm400710k]

Source

Source(1):

• Scientific Literature