2-[2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (1H-benzoimidazol-2-ylmethyl)-amide

ID: ALA109390

Chembl Id: CHEMBL109390

PubChem CID: 10345770

Max Phase: Preclinical

Molecular Formula: C29H31N5O3

Molecular Weight: 497.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: UFP-502 | UFP-502|CHEMBL109390|H-Dmt-Tic-NH-CH2-Bid|2-[2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (1H-benzoimidazol-2-ylmethyl)-amide|BDBM50179191|(S)-N-((1H-benzo[d]imidazol-2-yl)methyl)-2-((S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)NCc1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C29H31N5O3/c1-17-11-21(35)12-18(2)22(17)14-23(30)29(37)34-16-20-8-4-3-7-19(20)13-26(34)28(36)31-15-27-32-24-9-5-6-10-25(24)33-27/h3-12,23,26,35H,13-16,30H2,1-2H3,(H,31,36)(H,32,33)/t23-,26-/m0/s1

Standard InChI Key:  XRZTZWCPHAJWJQ-OZXSUGGESA-N

Alternative Forms

1. Parent:

   

   ALA109390

   (S)-N-((1H-benzo[d]imidazol-2-yl)methyl)-2-((S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

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: 497.60

Molecular Weight (Monoisotopic): 497.2427

AlogP: 3.03

#Rotatable Bonds: 6

Polar Surface Area: 124.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 7.75

CX LogP: 3.30

CX LogD: 2.88

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: -0.68

References

1. Balboni G, Salvadori S, Guerrini R, Negri L, Giannini E, Jinsmaa Y, Bryant SD, Lazarus LH..  (2002)  Potent delta-opioid receptor agonists containing the Dmt-Tic pharmacophore.,  45  (25): [PMID:12459023] [10.1021/jm020336e]

2. Balboni G, Guerrini R, Salvadori S, Bianchi C, Rizzi D, Bryant SD, Lazarus LH..  (2002)  Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties.,  45  (3): [PMID:11806723] [10.1021/jm010449i]

3. Balboni G, Guerrini R, Salvadori S, Negri L, Giannini E, Bryant SD, Jinsmaa Y, Lazarus LH..  (2005)  Conversion of the potent delta-opioid agonist H-Dmt-Tic-NH-CH(2)-bid into delta-opioid antagonists by N(1)-benzimidazole alkylation(1).,  48  (26): [PMID:16366592] [10.1021/jm058259l]

4. Salvadori S, Fiorini S, Trapella C, Porreca F, Davis P, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Balboni G..  (2008)  Role of benzimidazole (Bid) in the delta-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH(2)-Bid (UFP-502).,  16  (6): [PMID:18178091] [10.1016/j.bmc.2007.12.032]

5. Balboni G, Fiorini S, Baldisserotto A, Trapella C, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S..  (2008)  Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic.,  51  (16): [PMID:18680274] [10.1021/jm800587e]

6. Balboni G, Marzola E, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S..  (2010)  Role of 2',6'-dimethyl-l-tyrosine (Dmt) in some opioid lead compounds.,  18  (16): [PMID:20637637] [10.1016/j.bmc.2010.06.073]

Source

Source(1):

• Scientific Literature