(2S,5R,8S,11S,14S)-14,17-diamino-8-benzyl-2,11-bis(3-guanidinopropyl)-5-(hydroxymethyl)-4,7,10,13,17-pentaoxo-3,6,9,12-tetraazaheptadecan-1-oic acid

ID: ALA3633447

Chembl Id: CHEMBL3633447

PubChem CID: 122195270

Max Phase: Preclinical

Molecular Formula: C29H48N12O8

Molecular Weight: 692.78

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H48N12O8/c30-17(10-11-22(31)43)23(44)38-18(8-4-12-36-28(32)33)24(45)40-20(14-16-6-2-1-3-7-16)25(46)41-21(15-42)26(47)39-19(27(48)49)9-5-13-37-29(34)35/h1-3,6-7,17-21,42H,4-5,8-15,30H2,(H2,31,43)(H,38,44)(H,39,47)(H,40,45)(H,41,46)(H,48,49)(H4,32,33,36)(H4,34,35,37)/t17-,18-,19-,20-,21+/m0/s1

Standard InChI Key:  TWWFCOBVAKAKIT-UQVNRYHBSA-N

Alternative Forms

1. Parent:

   

   ALA3633447

   ---

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: 692.78

Molecular Weight (Monoisotopic): 692.3718

AlogP: -4.64

#Rotatable Bonds: 23

Polar Surface Area: 366.84

Molecular Species: ZWITTERION

HBA: 10

HBD: 14

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 18

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.86

CX Basic pKa: 11.58

CX LogP: -7.28

CX LogD: -9.77

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.03

Np Likeness Score: 0.26

References

1. Rosa M, Marcelo F, Calle LP, Rougeot C, Jiménez-Barbero J, Arsequell G, Valencia G..  (2015)  Influence of polar side chains modifications on the dual enkephalinase inhibitory activity and conformation of human opiorphin, a pain perception related peptide.,  25  (22): [PMID:26463133] [10.1016/j.bmcl.2015.09.071]

Source

Source(1):

• Scientific Literature