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

ID: ALA555206

Chembl Id: CHEMBL555206

PubChem CID: 45273695

Max Phase: Preclinical

Molecular Formula: C39H42N4O6

Molecular Weight: 662.79

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](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/C39H42N4O6/c1-24-17-30(44)18-25(2)31(24)22-32(40)38(47)43-23-29-16-10-9-15-28(29)21-35(43)37(46)41-33(19-26-11-5-3-6-12-26)36(45)42-34(39(48)49)20-27-13-7-4-8-14-27/h3-18,32-35,44H,19-23,40H2,1-2H3,(H,41,46)(H,42,45)(H,48,49)/t32-,33-,34-,35-/m0/s1

Standard InChI Key:  SZIMPGYQGJRODH-BBACVFHCSA-N

Alternative Forms

1. Parent:

   

   ALA555206

   H-2',6'-dimethyltyrosine-Tic-Phe-Phe-OH

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: 662.79

Molecular Weight (Monoisotopic): 662.3104

AlogP: 3.37

#Rotatable Bonds: 12

Polar Surface Area: 162.06

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.83

CX Basic pKa: 7.75

CX LogP: 2.87

CX LogD: 2.73

Aromatic Rings: 4

Heavy Atoms: 49

QED Weighted: 0.16

Np Likeness Score: -0.05

References

1. Balboni G, Trapella C, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S..  (2009)  Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore.,  52  (17): [PMID:19642675] [10.1021/jm900686q]

2. Berezowska I, Chung NN, Lemieux C, Wilkes BC, Schiller PW..  (2009)  Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).,  52  (21): [PMID:19827750] [10.1021/jm9004913]

3. Lee YS, Qu HC, Davis P, Ma SW, Vardanyan R, Lai J, Porreca F, Hruby VJ..  (2013)  Chiral Effect of a Phe Residue in Position 3 of the Dmt(1)-L(or D)-Tic(2) Analogues on Opioid Functional Activities.,  4  (7): [PMID:24648867] [10.1021/ml400115n]

4. 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