ChemComp-KVS: N~2~-[(2R,5S)-5-({(2S,3S)-2-[(N-acetyl-L-threonyl)amino]-3-methyl...

Basic information

• Entry: Database: PDB chemical components / ID: KVS
• Name: Name: N~2~-[(2R,5S)-5-({(2S,3S)-2-[(N-acetyl-L-threonyl)amino]-3-methylpent-4-enoyl}amino)-2-butyl-4,4-dihydroxynonanoyl]-L-glutaminyl-L-argininamide

BIRD information

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

Synonyms

• Ac-Thr-Ile-Nle psi[CO-CH(2)]Nle-Gln-Arg.amide (PDB)
• N~2~-[(2r,5s)-5-({(2s,3s)-2-[(N-Acetyl-L-Threonyl)amino]-3-Methylpent-4-Enoyl}amino)-2-Butyl-4,4-Dihydroxynonanoyl]-L-Glutaminyl-L-Argininamide (PubChem)

Annotation

• Function: Inhibitor of HIV-1 PROTEASE, EC: 3.4.23.16EC: Inhibitor of HIV-1 PROTEASE, EC: 3.4.23.16 / Info source: PubMed: 18657969

External info

• PubChem: 24875316

Family

ketomethylene isostere inhibitor

N~2~-[(2R,5S)-5-({(2S,3S)-2-[(N-acetyl-L-threonyl)amino]-3-methylpent-4-enoyl}amino)-2-butyl-4,4-dihydroxynonanoyl]-L-glutaminyl-L-argininamide

Chemical information

Composition

Formula: C₃₆H₆₈N₁₀O₁₀ / Number of atoms: 124 / Formula weight: 800.986 / Formal charge: 0

Others

3nwx

ACE

THR

ILE

NLH

GLN

ARG

NH2

Type: NON-POLYMER / PDB classification: HETAIN / Three letter code: KVS / Ideal coordinates details: Corina / Model coordinates PDB-ID: 3NWX / Subcomponent: ACE, THR, ILE, NLH, GLN, ARG, NH2

History

Create component	Jan 13, 2011
Modify descriptor	Jun 4, 2011
Other modification	Jul 25, 2019

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

Details

SMILES

• ACDLabs 12.01: C(=O)(C)NC(C(NC(C(=O)NC(C(O)(CC(C(NC(C(NC(C(N)=O)CCCN/C(N)=N)=O)CCC(N)=O)=O)CCCC)O)CCCC)C(C)CC)=O)C(C)O
• CACTVS 3.385: CCCC[CH](CC(O)(O)[CH](CCCC)NC(=O)[CH](NC(=O)[CH](NC(C)=O)[CH](C)O)[CH](C)CC)C(=O)N[CH](CCC(N)=O)C(=O)N[CH](CCCNC(N)=N)C(N)=O
• OpenEye OEToolkits 1.7.6: CCCCC(CC(C(CCCC)NC(=O)C(C(C)CC)NC(=O)C(C(C)O)NC(=O)C)(O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)N

SMILES CANONICAL

• CACTVS 3.385: CCCC[C@H](CC(O)(O)[C@H](CCCC)NC(=O)[C@@H](NC(=O)[C@@H](NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O
• OpenEye OEToolkits 1.7.6: [H]/N=C(\N)/NCCC[C@@H](C(=O)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCC)CC([C@H](CCCC)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)O)NC(=O)C)(O)O

InChI

• InChI 1.03: InChI=1S/C36H68N10O10/c1-7-10-13-23(31(51)44-25(16-17-27(37)49)32(52)43-24(30(38)50)14-12-18-41-35(39)40)19-36(55,56)26(15-11-8-2)45-33(53)28(20(4)9-3)46-34(54)29(21(5)47)42-22(6)48/h20-21,23-26,28-29,47,55-56H,7-19H2,1-6H3,(H2,37,49)(H2,38,50)(H,42,48)(H,43,52)(H,44,51)(H,45,53)(H,46,54)(H4,39,40,41)/t20-,21+,23+,24-,25-,26-,28-,29-/m0/s1

InChIKey

• InChI 1.03: GHZIZWOGRIROFP-WZGNFWQUSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (2S)-2-{[(2R,5S)-5-{[(2S,3S)-2-{[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]amino}-3-methylpentanoyl]amino}-2-butyl-4,4-dihydroxynonanoyl]amino}-N~1~-[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]pentanediamide (non-preferred name)
• OpenEye OEToolkits 1.7.6: (2S)-2-[[(2R,5S)-5-[[(2S,3S)-2-[[(2S,3R)-2-acetamido-3-oxidanyl-butanoyl]amino]-3-methyl-pentanoyl]amino]-2-butyl-4,4-bis(oxidanyl)nonanoyl]amino]-N-[(2S)-1-azanyl-5-carbamimidamido-1-oxidanylidene-pentan-2-yl]pentanediamide

PDB entries

Showing all 5 items

PDB-3dcr:
X-ray structure of HIV-1 protease and hydrated form of ketomethylene isostere inhibitor

PDB-3nwx:
X-ray structure of ester chemical analogue [O-Ile50,O-Ile50']HIV-1 protease complexed with KVS-1 inhibitor

PDB-3nxn:
X-ray structure of ester chemical analogue 'covalent dimer' [Ile50,O-Ile50']HIV-1 protease complexed with KVS-1 inhibitor

PDB-6kmp:
100K X-ray structure of HIV-1 protease triple mutant (V32I,I47V,V82I) with tetrahedral intermediate mimic KVS-1

PDB-6ptp:
Joint X-ray/neutron structure of HIV-1 protease triple mutant (V32I,I47V,V82I) with tetrahedral intermediate mimic KVS-1