2-{2-[2-(3-Amino-2-hydroxy-5-methyl-hexanoylamino)-3-methyl-butyrylamino]-3-methyl-butyrylamino}-succinic acid

ID: ALA28650

Chembl Id: CHEMBL28650

Cas Number: 67655-94-1

PubChem CID: 439518

Max Phase: Preclinical

Molecular Formula: C21H38N4O8

Molecular Weight: 474.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H38N4O8/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33)/t12-,13+,15+,16+,17+/m1/s1

Standard InChI Key:  QFAADIRHLBXJJS-ZAZJUGBXSA-N

Alternative Forms

1. Parent:

   

   ALA28650

   AMASTATIN

Molecule Features

Natural Product: Yes

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: 474.56

Molecular Weight (Monoisotopic): 474.2690

AlogP: -0.95

#Rotatable Bonds: 14

Polar Surface Area: 208.15

Molecular Species: ZWITTERION

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.54

CX Basic pKa: 8.77

CX LogP: -2.78

CX LogD: -5.02

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.17

Np Likeness Score: 0.40

References

1. Chauvel EN, Coric P, Llorens-Cortès C, Wilk S, Roques BP, Fournié-Zaluski MC..  (1994)  Investigation of the active site of aminopeptidase A using a series of new thiol-containing inhibitors.,  37  (9): [PMID:7909847] [10.1021/jm00035a014]

2. Harbeson SL, Rich DH..  (1989)  Inhibition of aminopeptidases by peptides containing ketomethylene and hydroxyethylene amide bond replacements.,  32  (6): [PMID:2566685] [10.1021/jm00126a039]

3. Grembecka J, Mucha A, Cierpicki T, Kafarski P..  (2003)  The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity.,  46  (13): [PMID:12801228] [10.1021/jm030795v]

4. Rich DH, Moon BJ, Harbeson S..  (1984)  Inhibition of aminopeptidases by amastatin and bestatin derivatives. Effect of inhibitor structure on slow-binding processes.,  27  (4): [PMID:6142952] [10.1021/jm00370a001]

Source

Source(1):

• Scientific Literature