(2S)-2-((2S)-2-(2-((S)-2-guanidino-3-(4-hydroxyphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-3-phenylpropanamido)-3-phenylpropanoic acid

ID: ALA3038187

Chembl Id: CHEMBL3038187

PubChem CID: 73349753

Max Phase: Preclinical

Molecular Formula: C38H40N6O6

Molecular Weight: 676.77

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  N=C(N)N[C@@H](Cc1ccc(O)cc1)C(=O)N1Cc2ccccc2C[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C38H40N6O6/c39-38(40)43-31(20-26-15-17-29(45)18-16-26)36(48)44-23-28-14-8-7-13-27(28)22-33(44)35(47)41-30(19-24-9-3-1-4-10-24)34(46)42-32(37(49)50)21-25-11-5-2-6-12-25/h1-18,30-33,45H,19-23H2,(H,41,47)(H,42,46)(H,49,50)(H4,39,40,43)/t30-,31-,32-,33-/m0/s1

Standard InChI Key:  VJIZTZDGNUBQTD-YRCZKMHPSA-N

Alternative Forms

1. Parent:

   

   ALA3038187

   (2S)-2-[[(2S)-2-[[(3S)-2-[(2S)-2-(diaminomethylideneamino)-3-(4-hydroxyphenyl)propanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoic acid

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: 676.77

Molecular Weight (Monoisotopic): 676.3009

AlogP: 2.28

#Rotatable Bonds: 13

Polar Surface Area: 197.94

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.83

CX Basic pKa: 11.32

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.08

Np Likeness Score: -0.07

References

1. Weltrowska G, Nguyen TM, Chung NN, Wilkes BC, Schiller PW..  (2013)  N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.,  23  (18): [PMID:23932788] [10.1016/j.bmcl.2013.07.036]

Source

Source(1):

• Scientific Literature