BIRD-PRD_000346: N-{(2R)-3-phenyl-2-[(L-prolyl-L-threonyl-L-alpha-glutamyl)amino]p...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000346
• Status: Status: REF ONLY
• Name: N-{(2R)-3-phenyl-2-[(L-prolyl-L-threonyl-L-alpha-glutamyl)amino]propyl}-L-phenylalanyl-N~5~-[amino(iminio)methyl]- L-ornithyl-L-glutamic acid

BIRD information

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

Synonyms

• H 256 (proteinase inhibitor) (Scifinder)
• H256 (PDB, PubChem, ChemSpider)
• L-Glutamic acid, L-prolyl-L-threonyl-L-alpha-glutamyl-L-phenylalanyl-psi(CH2-NH)-L-phenylalanyl-L-arginyl-(9CI) (Scifinder)
• L-Glutamic acid, N-(N2-(N-(3-phenyl-2-((N-(N-L-prolyl-L-threonyl)-L-alpha-glutamy l)amino)propyl)-L-phenylalanyl)-L-arginyl)-, (S)- (ChemSpider)
• L-Glutamic acid, N-(N2-(N-(3-phenyl-2-((N-(N-L-prolyl-Lthreonyml)-L-alpha-glutamyl)amino)propyl)-L-phenylalanyl)-L-arginyl)-,(s)- (PubChem)
• L-Glutamic acid, N-[N2-[N-[3-phenyl-2-[[N-(N-L-prolyl-L-threonyl)-L-alpha-glutamyl]amino]propyl]-L-phenylalanyl]-L-arginyl]-, (S)- (Scifinder)
• Pro-thr-glu-phe-CH2NH-phe-arg-glu (PubChem)
• Pro-thr-glu-phe-CH2NH-phe-arg-gluyl-2-((N-(N-L-prolyl-L-threonyl)-L-alpha-glutamy l)amino)propyl)-L-phenylalanyl)-L-arginyl)-, (S)- (ChemSpider)

Annotation

• Function: inhibitor of pepsin / Info source: PubChem
• Function: Inhibitor of ENDOTHIAPEPSIN, EC: 3.4.23.6EC: Inhibitor of ENDOTHIAPEPSIN, EC: 3.4.23.6 / Info source: PubMed: 3119339
• Mechanism of Action: in place of the scissile bond, a reduced peptide group which is resistant to hydrolysis and mimics the tetrahedral transition state / Info source: PubMed: 3119339

External info

• ChemIDplus: 100111088
• ChemSpider: 129595
• ChEBI: 252478
• PubChem: 146956
• CAS: 100111-08-8
• [MeSH_Unique_ID] MeSH: C054285

Family

H256

N-{(2R)-3-phenyl-2-[(L-prolyl-L-threonyl-L-alpha-glutamyl)amino]propyl}-L-phenylalanyl-N~5~-[amino(iminio)methyl]- L-ornithyl-L-glutamic acid

Chemical information

Composition

Formula: C₄₃H₆₃N₁₀O₁₂ / Formula weight: 912.02

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(NC(C(=O)NC(C(=O)NC(Cc1ccccc1)CNC(C(=O)NC(C(=O)NC(C(=O)O)CCC(=O)O)CCCNC(=[NH2+])/N)Cc2ccccc2)CCC(=O)O)C(O)C)C3NCCC3
• CACTVS 3.370: C[CH](O)[CH](NC(=O)[CH]1CCCN1)C(=O)N[CH](CCC(O)=O)C(=O)N[CH](CN[CH](Cc2ccccc2)C(=O)N[CH](CCCNC(N)=[NH2+])C(=O)N[CH](CCC(O)=O)C(O)=O)Cc3ccccc3
• OpenEye OEToolkits 1.7.6: CC(C(C(=O)NC(CCC(=O)O)C(=O)NC(Cc1ccccc1)CNC(Cc2ccccc2)C(=O)NC(CCCNC(=[NH2+])N)C(=O)NC(CCC(=O)O)C(=O)O)NC(=O)C3CCCN3)O

SMILES CANONICAL

• CACTVS 3.370: C[C@@H](O)[C@H](NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](CN[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](CCC(O)=O)C(O)=O)Cc3ccccc3
• OpenEye OEToolkits 1.7.6: C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)CN[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCCNC(=[NH2+])N)C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@@H]3CCCN3)O

InChI

• InChI 1.03: InChI=1S/C43H62N10O12/c1-25(54)36(53-37(59)29-14-8-20-46-29)41(63)51-31(16-18-34(55)56)38(60)49-28(22-26-10-4-2-5-11-26)24-48-33(23-27-12-6-3-7-13-27)40(62)50-30(15-9-21-47-43(44)45)39(61)52-32(42(64)65)17-19-35(57)58/h2-7,10-13,25,28-33,36,46,48,54H,8-9,14-24H2,1H3,(H,49,60)(H,50,62)(H,51,63)(H,52,61)(H,53,59)(H,55,56)(H,57,58)(H,64,65)(H4,44,45,47)/p+1/t25-,28+,29-,30?,31-,32-,33-,36+/m0/s1

InChIKey

• InChI 1.03: WNWJVPXOYQRRNI-BOJKBDEQSA-O

SYSTEMATIC NAME

• ACDLabs 12.01: N-{(2R)-3-phenyl-2-[(L-prolyl-L-threonyl-L-alpha-glutamyl)amino]propyl}-L-phenylalanyl-N~5~-[amino(iminio)methyl]-L-ornithyl-L-glutamic acid
• OpenEye OEToolkits 1.7.6: [azanyl-[[(4S)-5-[[(2S)-1,5-bis(oxidanyl)-1,5-bis(oxidanylidene)pentan-2-yl]amino]-5-oxidanylidene-4-[[(2S)-2-[[(2S)-2-[[(2S)-5-oxidanyl-5-oxidanylidene-2-[[(2S,3R)-3-oxidanyl-2-[[(2S)-pyrrolidin-2-yl]carbonylamino]butanoyl]amino]pentanoyl]amino]-3-phenyl-propyl]amino]-3-phenyl-propanoyl]amino]pentyl]amino]methylidene]azanium

PDB entries

Showing all 2 items

PDB-1gvx:
Endothiapepsin complexed with H256

PDB-2er6:
The structure of a synthetic pepsin inhibitor complexed with endothiapepsin.