(2S)-2-((2S)-2-(2-((S)-2-guanidino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-3-phenylpropanamido)-3-phenylpropanoic acid

ID: ALA3038186

Chembl Id: CHEMBL3038186

PubChem CID: 73352754

Max Phase: Preclinical

Molecular Formula: C40H44N6O6

Molecular Weight: 704.83

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](NC(=N)N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C40H44N6O6/c1-24-17-30(47)18-25(2)31(24)22-33(45-40(41)42)38(50)46-23-29-16-10-9-15-28(29)21-35(46)37(49)43-32(19-26-11-5-3-6-12-26)36(48)44-34(39(51)52)20-27-13-7-4-8-14-27/h3-18,32-35,47H,19-23H2,1-2H3,(H,43,49)(H,44,48)(H,51,52)(H4,41,42,45)/t32-,33-,34-,35-/m0/s1

Standard InChI Key:  GMXYZKQOJAODEJ-BBACVFHCSA-N

Alternative Forms

1. Parent:

   

   ALA3038186

   (2S)-2-[[(2S)-2-[[(3S)-2-[(2S)-2-(diaminomethylideneamino)-3-(4-hydroxy-2,6-dimethylphenyl)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: 704.83

Molecular Weight (Monoisotopic): 704.3322

AlogP: 2.90

#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: 11.38

CX LogP: 3.16

CX LogD: 3.15

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.08

Np Likeness Score: -0.04

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