ChemComp-0ZR: N-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl...

Basic information

• Entry: Database: PDB chemical components / ID: 0ZR
• Name: Name: N-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}-L-phenylalanyl-L-glutaminyl-L-phenylalaninamide

BIRD information

• Type: Peptide-like / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• Boc-Phe-.phi.[(S)-CH(OH)CH2NH]Phe-Gln-Phe-NH2 (PubChem)
• Boc-Phe-psi[S-CH(OH)CH2NH]Phe-Gln-Phe-NH2 (PubChem)
• Boc-Phe[CH(OH)CH2NH]Phe-Gln-Phe-NH2 (ChemSpider)
• L-Phenylalaninamide, N-[(2S,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-phenylalanyl-L-glutaminyl-(9CI) (Scifinder)
• N-{(2R,3S)-3-[(tert-Butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}-L-phenylalanyl-L-glutaminyl-L-phenylalaninamide (ChemSpider)
• N-{(2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}-L-phenylalanyl-L-glutaminyl-L-phenylalaninamide (PubChem)

Annotation

• Function: Inhibitor of PROTEASE RETROPEPSIN (HIV-1 PROTEASE), EC: 3.4.23.16EC: Inhibitor of PROTEASE RETROPEPSIN (HIV-1 PROTEASE), EC: 3.4.23.16 / Info source: PubMed: 11906284

External info

• BindingDB: 17349
• ChemSpider: 393690
• ChEBI: 459125
• PubChem: 446293

Family

ethyleneamine containing linear peptidomimetic inhibitor

BOC-PHE-PSI[CH2CH2NH]-PHE-GLU-PHE-NH2 / BOC-PS0-PHE-GLN-PHE-NH2 / BOC-PHE-PSI[R-CH(OH)CH2NH]-PHE-GLU-PHE-NH2 / BOC-PHE-PSI[S-CH(OH)CH2NH]-PHE-GLU-PHE-NH2

Chemical information

Composition

Formula: C₃₈H₅₀N₆O₇ / Number of atoms: 101 / Formula weight: 702.84 / Formal charge: 0

Others

1iiq

BOC

R00

GLN

PHE

NH2

Type: peptide-like / PDB classification: HETAIN / Three letter code: 0ZR / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1iiq / Model coordinates details: not provided / Subcomponent: BOC, R00, GLN, PHE, NH2

History

Create component	Aug 12, 2008
Other modification	Nov 17, 2010
Modify aromatic flag	Jun 4, 2011
Modify descriptor	Jun 4, 2011

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(N)C(NC(=O)C(NC(=O)C(NCC(O)C(NC(=O)OC(C)(C)C)Cc1ccccc1)Cc2ccccc2)CCC(=O)N)Cc3ccccc3
• CACTVS 3.370: CC(C)(C)OC(=O)N[CH](Cc1ccccc1)[CH](O)CN[CH](Cc2ccccc2)C(=O)N[CH](CCC(N)=O)C(=O)N[CH](Cc3ccccc3)C(N)=O
• OpenEye OEToolkits 1.7.0: CC(C)(C)OC(=O)NC(Cc1ccccc1)C(CNC(Cc2ccccc2)C(=O)NC(CCC(=O)N)C(=O)NC(Cc3ccccc3)C(=O)N)O

SMILES CANONICAL

• CACTVS 3.370: CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc3ccccc3)C(N)=O
• OpenEye OEToolkits 1.7.0: CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@H](CN[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc3ccccc3)C(=O)N)O

InChI

• InChI 1.03: InChI=1S/C38H50N6O7/c1-38(2,3)51-37(50)44-29(21-25-13-7-4-8-14-25)32(45)24-41-31(23-27-17-11-6-12-18-27)36(49)42-28(19-20-33(39)46)35(48)43-30(34(40)47)22-26-15-9-5-10-16-26/h4-18,28-32,41,45H,19-24H2,1-3H3,(H2,39,46)(H2,40,47)(H,42,49)(H,43,48)(H,44,50)/t28-,29-,30-,31-,32-/m0/s1

InChIKey

• InChI 1.03: SSPOMXWWHDMCTH-XDIGFQIYSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}-L-phenylalanyl-L-glutaminyl-L-phenylalaninamide
• OpenEye OEToolkits 1.7.0: tert-butyl N-[(2S,3S)-4-[[(2S)-1-[[(2S)-5-azanyl-1-[[(2S)-1-azanyl-1-oxo-3-phenyl-propan-2-yl]amino]-1,5-dioxo-pentan-2-yl]amino]-1-oxo-3-phenyl-propan-2-yl]amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate

PDB entries

Showing all 2 items

PDB-1iiq:
CRYSTAL STRUCTURE OF HIV-1 PROTEASE COMPLEXED WITH A HYDROXYETHYLAMINE PEPTIDOMIMETIC INHIBITOR

PDB-1zlf:
Crystal structure of a complex of mutant HIV-1 protease (A71V, V82T, I84V) with a hydroxyethylamine peptidomimetic inhibitor