BIRD-PRD_000362: INHIBITOR VAL-SER-GLN-ASN-LEU-PSI(CH(OH)-CH2)-VAL-ILE-VAL (U-85548E)

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000362
• Status: Status: REF ONLY
• Name: INHIBITOR VAL-SER-GLN-ASN-LEU-PSI(CH(OH)-CH2)-VAL-ILE-VAL (U-85548E)

BIRD information

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

Synonyms

• 85548e62-8 (ChemSpider)
• H-Val-Ser-Gln-Asn-Leu-.psi.[CH(OH)CH2]-Val-Ile-Val-OH (PubChem)
• L-Valine, L-valyl-L-seryl-L-glutaminyl-L-asparaginyl-(2S,4S,5S)-5-amino-4-hydroxy-7-methyl-2-(1-methylethyl)octanoyl-L-isoleucyl- (Scifinder)
• L-Valine, N-(N-(4-hydroxy-7-methyl-2-(1-methylethyl)-1-oxo-5-((N2-(N2-(N -L-valyl-L-seryl)-L-glutaminyl)-L-asparaginyl)amino)octyl)-L-isoleucyl)-, (2S-(2R*,4R*,5R*))- (ChemSpider)
• L-Valine, N-[N-[4-hydroxy-7-methyl-2-(1-methylethyl)-1-oxo-5-[[N2-[N2-(N-L-valyl-L-seryl)-L-glutaminyl]-L-asparaginyl]amino]octyl]-L-isoleucyl]-, [2S-(2R*,4R*,5R*)]- (Scifinder)
• U 85548 (Scifinder)
• U 85548E (Scifinder)
• U 85548e-8 (ChemSpider)
• U-85548E (PDB)
• U85548e (PubChem)
• Val-ser-gln-asn-leu-CH(OH)CH2-val-ile-val (ChemSpider)

Annotation

• Function: Inhibitor of HIV-1 PROTEASE / Info source: PubMed: 1993177

External info

• ChemSpider: 396087
• PubChem: 449613
• CAS: 124020-62-8

Family

VSQN-L-V hydroxyethylene isostere-IV inhibitor

INHIBITOR VAL-SER-GLN-ASN-LEU-PSI(CH(OH)-CH2)-VAL-ILE-VAL (U-85548E)

Chemical information

Composition

Formula: C₄₀H₇₃N₉O₁₂ / Formula weight: 872.061

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(O)C(NC(=O)C(NC(=O)C(C(C)C)CC(O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(N)C(C)C)CO)CCC(=O)N)CC(=O)N)CC(C)C)C(C)CC)C(C)C
• CACTVS 3.370: CC[CH](C)[CH](NC(=O)[CH](C[CH](O)[CH](CC(C)C)NC(=O)[CH](CC(N)=O)NC(=O)[CH](CCC(N)=O)NC(=O)[CH](CO)NC(=O)[CH](N)C(C)C)C(C)C)C(=O)N[CH](C(C)C)C(O)=O
• OpenEye OEToolkits 1.7.6: CCC(C)C(C(=O)NC(C(C)C)C(=O)O)NC(=O)C(CC(C(CC(C)C)NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(C(C)C)N)O)C(C)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@H](NC(=O)[C@@H](C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)C(C)C)C(C)C)C(=O)N[C@@H](C(C)C)C(O)=O
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)[C@@H](C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)N)O)C(C)C

InChI

• InChI 1.03: InChI=1S/C40H73N9O12/c1-11-22(10)33(39(59)48-32(21(8)9)40(60)61)49-34(54)23(19(4)5)15-28(51)25(14-18(2)3)45-36(56)26(16-30(42)53)46-35(55)24(12-13-29(41)52)44-37(57)27(17-50)47-38(58)31(43)20(6)7/h18-28,31-33,50-51H,11-17,43H2,1-10H3,(H2,41,52)(H2,42,53)(H,44,57)(H,45,56)(H,46,55)(H,47,58)(H,48,59)(H,49,54)(H,60,61)/t22-,23+,24-,25-,26+,27+,28+,31-,32+,33-/m0/s1

InChIKey

• InChI 1.03: BURQLNQHSQGPEJ-MWAYUVTLSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: L-valyl-L-seryl-L-glutaminyl-N~1~-[(4S,5R,7R)-7-{[(2S,3S)-1-{[(1R)-1-carboxy-2-methylpropyl]amino}-3-methyl-1-oxopentan-2-yl]carbamoyl}-5-hydroxy-2,8-dimethylnonan-4-yl]-L-aspartamide
• OpenEye OEToolkits 1.7.6: (2S)-2-[[(2S,3S)-2-[[(2S,4S,5S)-5-[[(2S)-4-azanyl-2-[[(2S)-5-azanyl-2-[[(2S)-2-[[(2S)-2-azanyl-3-methyl-butanoyl]amino]-3-oxidanyl-propanoyl]amino]-5-oxidanylidene-pentanoyl]amino]-4-oxidanylidene-butanoyl]amino]-7-methyl-4-oxidanyl-2-propan-2-yl-octanoyl]amino]-3-methyl-pentanoyl]amino]-3-methyl-butanoic acid

PDB entries

Showing all 1 items

PDB-8hvp:
STRUCTURE AT 2.5-ANGSTROMS RESOLUTION OF CHEMICALLY SYNTHESIZED HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 PROTEASE COMPLEXED WITH A HYDROXYETHYLENE*-BASED INHIBITOR