(4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one
Basic information
- CAS
151867-81-1- Standard SMILES
O=C1N(Cc2ccc(CO)cc2)[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H](Cc2ccccc2)N1Cc1ccc(CO)cc1- InChIKey
XCVGQMUMMDXKCY-WZJLIZBTSA-N- Molecular formula
- C35H38N2O5
- Average molar mass
- 566.7 g/mol
- Monoisotopic mass
- 566.27807232
Overview
(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one is a 1,3-diazepanone ring with two 4-(hydroxymethyl)benzyl groups as substituents at positions N-1 and N-4, two benzyl groups at C-4 and C-7, and two hydroxy groups at C-5 and C-6 respectively. It has a role as a metabolite and an anti-HIV agent. It is a diazepanone and a member of ureas.
Names & identifiers
- Preferred name
- (4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one
- IUPAC
- (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[[4-(hydroxymethyl)phenyl]methyl]-1,3-diazepan-2-one
- English name
- DMP 323
- Molecular formula
- C35H38N2O5
- Molecular weight
- 566.69
Names & synonyms
Dmp 323151867-81-1KXN3869XB2DTXSID40164892RefChem:906148DTXCID8087383(4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-oneDmp-323XM-323dmp323(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[[4-(hydroxymethyl)phenyl]methyl]-1,3-diazepan-2-one
Show more names
JCR4242H-1,3-Diazepin-2-one, hexahydro-5,6-dihydroxy-1,3-bis[[4-(hydroxymethyl)phenyl]methyl]-4,7-bis(phenylmethyl)-, (4R,5S,6S,7R)-
1mes(4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis(4-(hydroxymethyl)benzyl)-1,3-diazepan-2-one1met1meu1qbsJCR 424JCR-424XCVGQMUMMDXKCY-WZJLIZBTSA-N
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 735
Physicochemical properties
- Boiling point
- 798.6 · 798.6±60.0 °C(Predicted)
- Density
- 1.294 · 1.294±0.06 g/cm3(Predicted)
- pka
- 14.08 · 14.08±0.70(Predicted)
- FDA UNII
- 3869 XB2 · KXN3869XB2
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationInhibitors of HIV PROTEASE, an enzyme required for production of proteins needed for viral assembly.
Applications
UsesDMP 323 is a potent, nonpeptide cyclic urea inhibitor of HIV protease, effective against both HIV type 1 and type 2. Designed using structural information and database searching, it competitively inhibits the cleavage of both peptide and HIV-1 gag polyprotein substrates. DMP 323 shows comparable potency to other highly effective HIV protease inhibitors like A-80987 and Ro-31-8959. Importantly, its efficacy against HIV protease remains unaffected by human plasma or serum, suggesting low affinity for plasma proteins. Furthermore, DMP 323 demonstrates minimal inhibition of various mammalian proteases at concentrations much higher than those needed for HIV protease inhibition, highlighting its specificity for viral targets[1].
Additional notes
DefinitionChEBI: A 1,3-diazepanone ring with two 4-(hydroxymethyl)benzyl groups as substituents at positions N-1 and N-4, two benzyl groups at C-4 and C-7, and two hydroxy groups at C-5 and C-6 respectively.
Related reactions
1 records
Compound notes
Loading…