BIRD-PRD_000233: N-acetyl-3-cyclohexyl-L-alanyl-N~5~-[amino(iminio)methyl]-L-ornit...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000233
• Status: Status: REF ONLY
• Name: N-acetyl-3-cyclohexyl-L-alanyl-N~5~-[amino(iminio)methyl]-L-ornithyl-L-alanyl-L-methionyl-S-[(acetylamino)methyl]-L- cysteinyl-L-seryl-L-leucinamide

BIRD information

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

Synonyms

• (2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-cyclohexylpropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(acetamidomethylsulfanyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanamide (PubChem)
• Ac(Cha)ArgAlaMetCys(Acm)SerLeuNH2 (PubChem)
• Ac-(Cha)RAM(CAcm)SL-NH2 (PubChem)
• N-acetyl-3-cyclohexyl-L-alanyl-L-arginyl-L-alanyl-L-methionyl-S-(acetamidomethyl)-L-cysteinyl-L-seryl-L-leucinamide (PubChem)

Annotation

• Function: inhibitor of MHC class II HLA-DR binding / Info source: PubMed: 10841792

External info

• CHEBI: 62365
• PubChem: 444990

Family

Ac-(Cha)RAM containing peptide analog

N-acetyl-3-cyclohexyl-L-alanyl-N~5~-[amino(iminio)methyl]-L-ornithyl-L-alanyl-L-methionyl-S-[(acetylamino)methyl]-L- cysteinyl-L-seryl-L-leucinamide

Chemical information

Composition

Formula: C₄₀H₇₃N₁₂O₁₀S₂ / Formula weight: 946.212

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(N)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C)CC1CCCCC1)CCCNC(=[NH2+])\N)C)CCSC)CSCNC(=O)C)CO)CC(C)C
• CACTVS 3.370: CSCC[CH](NC(=O)[CH](C)NC(=O)[CH](CCCNC(N)=[NH2+])NC(=O)[CH](CC1CCCCC1)NC(C)=O)C(=O)N[CH](CSCNC(C)=O)C(=O)N[CH](CO)C(=O)N[CH](CC(C)C)C(N)=O
• OpenEye OEToolkits 1.7.6: CC(C)CC(C(=O)N)NC(=O)C(CO)NC(=O)C(CSCNC(=O)C)NC(=O)C(CCSC)NC(=O)C(C)NC(=O)C(CCCNC(=[NH2+])N)NC(=O)C(CC1CCCCC1)NC(=O)C

SMILES CANONICAL

• CACTVS 3.370: CSCC[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@H](CC1CCCCC1)NC(C)=O)C(=O)N[C@@H](CSCNC(C)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(N)=O
• OpenEye OEToolkits 1.7.6: C[C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CSCNC(=O)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N)NC(=O)[C@H](CCCNC(=[NH2+])N)NC(=O)[C@H](CC1CCCCC1)NC(=O)C

InChI

• InChI 1.03: InChI=1S/C40H72N12O10S2/c1-22(2)17-29(33(41)56)50-38(61)31(19-53)51-39(62)32(20-64-21-45-24(4)54)52-36(59)28(14-16-63-6)48-34(57)23(3)46-35(58)27(13-10-15-44-40(42)43)49-37(60)30(47-25(5)55)18-26-11-8-7-9-12-26/h22-23,26-32,53H,7-21H2,1-6H3,(H2,41,56)(H,45,54)(H,46,58)(H,47,55)(H,48,57)(H,49,60)(H,50,61)(H,51,62)(H,52,59)(H4,42,43,44)/p+1/t23?,27?,28?,29-,30?,31+,32-/m1/s1

InChIKey

• InChI 1.03: KHCSMHYTMQUQCE-KTSNBLDASA-O

SYSTEMATIC NAME

• ACDLabs 12.01: N-acetyl-3-cyclohexyl-L-alanyl-N~5~-[amino(iminio)methyl]-L-ornithyl-L-alanyl-L-methionyl-S-[(acetylamino)methyl]-L-cysteinyl-L-seryl-L-leucinamide
• OpenEye OEToolkits 1.7.6: [[[(4S)-4-[[(2S)-2-acetamido-3-cyclohexyl-propanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S)-1-[[(2S)-1-azanyl-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-3-oxidanyl-1-oxidanylidene-propan-2-yl]amino]-1-oxidanylidene-propan-2-yl]amino]-4-methylsulfanyl-1-oxidanylidene-butan-2-yl]amino]-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentyl]amino]-azanyl-methylidene]azanium

PDB entries

Showing all 1 items

PDB-1d5m:
X-RAY CRYSTAL STRUCTURE OF HLA-DR4 COMPLEXED WITH PEPTIDE AND SEB