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

ID: ALA3633453

Chembl Id: CHEMBL3633453

PubChem CID: 122195276

Max Phase: Preclinical

Molecular Formula: C37H61N13O13

Molecular Weight: 895.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@@H](OC[C@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CCC(N)=O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C37H61N13O13/c1-18(52)46-27-29(55)28(54)25(16-51)63-35(27)62-17-24(33(59)48-22(34(60)61)10-6-14-45-37(42)43)50-32(58)23(15-19-7-3-2-4-8-19)49-31(57)21(9-5-13-44-36(40)41)47-30(56)20(38)11-12-26(39)53/h2-4,7-8,20-25,27-29,35,51,54-55H,5-6,9-17,38H2,1H3,(H2,39,53)(H,46,52)(H,47,56)(H,48,59)(H,49,57)(H,50,58)(H,60,61)(H4,40,41,44)(H4,42,43,45)/t20-,21-,22-,23-,24-,25+,27+,28+,29+,35-/m0/s1

Standard InChI Key:  JDHTWBCWXCCGJS-RRWJDLRRSA-N

Alternative Forms

1. Parent:

   

   ALA3633453

   ---

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: 895.97

Molecular Weight (Monoisotopic): 895.4512

AlogP: -6.67

#Rotatable Bonds: 27

Polar Surface Area: 454.86

Molecular Species: ZWITTERION

HBA: 15

HBD: 17

#RO5 Violations: 3

HBA (Lipinski): 26

HBD (Lipinski): 21

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.66

CX Basic pKa: 11.82

CX LogP: -9.38

CX LogD: -11.83

Aromatic Rings: 1

Heavy Atoms: 63

QED Weighted: 0.02

Np Likeness Score: 0.56

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