(S)-2-(3-Amino-4-((S)-2-amino-5-guanidinopentanamido)-benzamido)-3-(1H-indol-3-yl)propanoic Acid

ID: ALA3416730

Chembl Id: CHEMBL3416730

PubChem CID: 118734297

Max Phase: Preclinical

Molecular Formula: C24H30N8O4

Molecular Weight: 494.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](N)C(=O)Nc1ccc(C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)O)cc1N

Standard InChI:  InChI=1S/C24H30N8O4/c25-16(5-3-9-29-24(27)28)22(34)31-19-8-7-13(10-17(19)26)21(33)32-20(23(35)36)11-14-12-30-18-6-2-1-4-15(14)18/h1-2,4,6-8,10,12,16,20,30H,3,5,9,11,25-26H2,(H,31,34)(H,32,33)(H,35,36)(H4,27,28,29)/t16-,20-/m0/s1

Standard InChI Key:  VAPOMUBVLCEHNL-JXFKEZNVSA-N

Alternative Forms

1. Parent:

   

   ALA3416730

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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: 494.56

Molecular Weight (Monoisotopic): 494.2390

AlogP: 0.70

#Rotatable Bonds: 11

Polar Surface Area: 225.23

Molecular Species: ZWITTERION

HBA: 6

HBD: 9

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.82

CX Basic pKa: 11.98

CX LogP: -1.66

CX LogD: -2.27

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.08

Np Likeness Score: -0.20

References

1. Papakyriakou A, Zervoudi E, Tsoukalidou S, Mauvais FX, Sfyroera G, Mastellos DC, van Endert P, Theodorakis EA, Vourloumis D, Stratikos E..  (2015)  3,4-diaminobenzoic acid derivatives as inhibitors of the oxytocinase subfamily of M1 aminopeptidases with immune-regulating properties.,  58  (3): [PMID:25635706] [10.1021/jm501867s]

Source

Source(1):

• Scientific Literature