(2S)-2-((2S)-2-((2-((S)-2-guanidino-3-(4-hydroxyphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)methylamino)-3-phenylpropanamido)-3-phenylpropanoic acid

ID: ALA3038182

Chembl Id: CHEMBL3038182

PubChem CID: 73354257

Max Phase: Preclinical

Molecular Formula: C38H42N6O5

Molecular Weight: 662.79

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C38H42N6O5/c39-38(40)43-33(20-27-15-17-31(45)18-16-27)36(47)44-24-29-14-8-7-13-28(29)22-30(44)23-41-32(19-25-9-3-1-4-10-25)35(46)42-34(37(48)49)21-26-11-5-2-6-12-26/h1-18,30,32-34,41,45H,19-24H2,(H,42,46)(H,48,49)(H4,39,40,43)/t30-,32-,33-,34-/m0/s1

Standard InChI Key:  ITTXXJPDPMIZNK-DYTOPAQESA-N

Alternative Forms

1. Parent:

   

   ALA3038182

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

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: 662.79

Molecular Weight (Monoisotopic): 662.3217

AlogP: 2.75

#Rotatable Bonds: 14

Polar Surface Area: 180.87

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.98

CX Basic pKa: 11.37

CX LogP: 2.52

CX LogD: 1.89

Aromatic Rings: 4

Heavy Atoms: 49

QED Weighted: 0.08

Np Likeness Score: 0.11

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