(2S,5S,8S,11S,14S)-5-((R)-1-((2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)ethyl)-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: ALA3633455

Chembl Id: CHEMBL3633455

PubChem CID: 122195278

Max Phase: Preclinical

Molecular Formula: C38H63N13O13

Molecular Weight: 910.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@@H](O[C@H](C)[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/C38H63N13O13/c1-18(63-36-28(47-19(2)53)30(56)29(55)25(17-52)64-36)27(34(60)49-23(35(61)62)11-7-15-46-38(43)44)51-33(59)24(16-20-8-4-3-5-9-20)50-32(58)22(10-6-14-45-37(41)42)48-31(57)21(39)12-13-26(40)54/h3-5,8-9,18,21-25,27-30,36,52,55-56H,6-7,10-17,39H2,1-2H3,(H2,40,54)(H,47,53)(H,48,57)(H,49,60)(H,50,58)(H,51,59)(H,61,62)(H4,41,42,45)(H4,43,44,46)/t18-,21+,22+,23+,24+,25-,27+,28-,29-,30-,36+/m1/s1

Standard InChI Key:  LSQMBMCEFHSRMB-FLDZCKPISA-N

Alternative Forms

1. Parent:

   

   ALA3633455

   ---

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: 910.00

Molecular Weight (Monoisotopic): 909.4668

AlogP: -6.28

#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: 3.71

CX Basic pKa: 12.18

CX LogP: -8.97

CX LogD: -11.41

Aromatic Rings: 1

Heavy Atoms: 64

QED Weighted: 0.02

Np Likeness Score: 0.61

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