BIRD-PRD_000765: CYCLOSPORIN A, 5 mutation

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000765
• Status: Status: REF ONLY
• Name: CYCLOSPORIN A, 5 mutation

BIRD information

• Type: Cyclic peptide / Immunosuppressant

Details

• CYCLOSPORIN IS A CYCLIC UNDECAPEPTIDE. HERE, CYCLOSPORIN A IS REPRESENTED BY THE SEQUENCE (SEQRES)
• CYCLOSPORIN IS A CYCLIC UNDECAPEPTIDE. CYCLIZATION IS ACHIEVED BY LINKING THE N- AND THE C- TERMINI. THE CYCLOSPORIN WAS MODIFIED AT POSITION 5 TO BE 4-[(E)-2-BUTENYL]-4,4,N-TRIMETHYL-L-THREONINE

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• N-methyl-4-[(E)-2-butenyl]-4,4-dimethylthreonine cyclosporin A (PDB)

Annotation

• Function: immunosuppressive drug, binds cyclosporin A (PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A), EC: 5.2.1.8EC: immunosuppressive drug, binds cyclosporin A (PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A), EC: 5.2.1.8 / Info source: PubMed: 8075981

Family

Cyclosporin

Cyclosporin A / Cyclosporin D / Cyclosporin C / CYCLOSPORIN D, 5,7 mutation / CYCLOSPORIN A, 5 mutation / CYCLOSPORIN A, 6 mutation / CYCLOSPORIN A, 7 mutation / CYCLOSPORIN A, 8 mutation / Cyclosporin A variant, MLE 8 to MNL / Cyclosporin D variant, MSA 7 to MAA / Cyclosporin C variant (DAL 1 to VAD, MLE 3 to LEU, VAL 9 to LEU) / Mutant CYCLOSPORIN D

Related structures

• Iodo-cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: ICYSPA / Reference
• Cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: DEKSAN / Reference
• Cyclosporin A monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KEPNAU / Reference
• (-4-PSI-5-,CS-NH,-7-PSI-8-,CS-NH)-Cyclosporin A diethyl ether solvate, seqres C11 ALA*-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: JOKMAX / Reference
• methyl((4S)-METHYL)NORLEU-4 Cyclosporin cyclophilin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LIKNIC / Reference
• cyclo-(alanyl-d-alanyl-n-methylleucyl-n-methylleucyl-N-methylvalyl-alpha-(1-oxo-2-methylhex-4-enyl)sarcosyl-valyl-sarcosyl-N-methylleucyl-valyl-N-methylleucyl), seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-VAL*-SAR-LEU*-VAL-LEU*- / CCDC: ZADRIF / Reference
• sulfhydryl cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: ZAJDUJ / Reference
• isocyclosporin A acetone solvate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*,GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: NAMPIA / Reference
• cyclosporin A dimethylisosorbide solvate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: TECRIC / Reference
• cyclosporin E acetone solveate monohydrate clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: SUQNUN / Reference
• O-acetyl-(4R)-4-(E-2-butenyl)-4,N-dimethyl-L-threonylcyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: CUQRUB / Reference
• O-acetyl-(4R)-4-(4-bromobutyl)-4,N-dimethyl-L-threonylcyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: CUQSAI / Reference
• cyclosporin H diethyl ether solvate monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: DUDQAU / Reference
• cyclosporin V t-butyl methyl ether clathrate, seqres C11 GLY*-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: HUCVIK / Reference
• dihydrocyclosporin A t-butyl methyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: HUCVOQ / Reference
• cyclosporin A tetrahydrofuran clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWGOT / Reference
• cyclosporin A di-n-butyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWHAG / Reference
• cyclosporin A di-n-butyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWHAG01 / Reference
• cyclosporin G methanol solvate hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-NVA-SAR-LEU*-VAL-LEU*- / CCDC: GABWOW / Reference
• cyclosporin G methanol solvate hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-NVA-SAR-LEU*-VAL-LEU*- / CCDC: GABWUC / Reference
• cyclosporin H hexahydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: GABXAJ / Reference
• cyclosporin H hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: GABXEN / Reference
• cyclosporin A acetone monohydrate clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KADFOL / Reference
• cyclo-(alanyl-D-alanyl-N-methylleucyl-N-methylleucyl-N-methylvalyl-alpha-(1-oxo-2-methylhex-4-enyl)sarcosyl-valyl-sarcosyl-N-methylleucyl-valyl-N-methylleucyl) di-isopropyl ether solvate hemihydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-VAL*-SAR-LEU*-VAL-LEU*- / CCDC: ZADREB / Reference
• Cyclosporin A monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KEPNAU01
• Cyclosporin A hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOSLEL

Chemical information

Composition

Formula: C₆₃H₁₁₃N₁₁O₁₂ / Formula weight: 1216.638

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C1N(C)C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C)C(C(=O)N(C)C(C(=O)N(C)C(C(=O)N(C)C(C(=O)NC(C(=O)N(C)C1)CC)C(O)C(C)(C)C\C=C/C)C(C)C)CC(C)C)CC(C)C)C)C)CC(C)C)C)C(C)C)CC(C)C
• CACTVS 3.370: CC[CH]1NC(=O)[CH]([CH](O)C(C)(C)CC=CC)N(C)C(=O)[CH](C(C)C)N(C)C(=O)[CH](CC(C)C)N(C)C(=O)[CH](CC(C)C)N(C)C(=O)[CH](C)NC(=O)[CH](C)NC(=O)[CH](CC(C)C)N(C)C(=O)[CH](NC(=O)[CH](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
• OpenEye OEToolkits 1.7.6: CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@@H]1NC(=O)[C@H]([C@H](O)C(C)(C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
• OpenEye OEToolkits 1.7.6: CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H](C(C)(C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

InChI

• InChI 1.03: InChI=1S/C63H113N11O12/c1-26-28-29-63(17,18)52(76)51-56(80)66-43(27-2)58(82)68(19)34-48(75)69(20)44(30-35(3)4)55(79)67-49(39(11)12)61(85)70(21)45(31-36(5)6)54(78)64-41(15)53(77)65-42(16)57(81)71(22)46(32-37(7)8)59(83)72(23)47(33-38(9)10)60(84)73(24)50(40(13)14)62(86)74(51)25/h26,28,35-47,49-52,76H,27,29-34H2,1-25H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b28-26-/t41-,42-,43-,44-,45-,46-,47+,49+,50-,51+,52+/m1/s1

InChIKey

• InChI 1.03: RGIOCYRKFMXZGI-JGHWQVNISA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (3R,6S,9R,12R,15R,18R,21S,24R,30R,33S)-30-ethyl-33-[(1R,4E)-1-hydroxy-2,2-dimethylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• OpenEye OEToolkits 1.7.6: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R)-2,2-dimethyl-1-oxidanyl-hex-4-enyl]-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone

PDB entries

Showing all 2 items

PDB-1cwb:
THE X-RAY STRUCTURE OF (MEBM2T)1-CYCLOSPORIN COMPLEXED WITH CYCLOPHILIN A PROVIDES AN EXPLANATION FOR ITS ANOMALOUSLY HIGH IMMUNOSUPPRESSIVE ACTIVITY

PDB-2rmb:
Crystal structures of cyclophilin A complexed with cyclosporin A and N-methyl-4-[(E)-2-butenyl]-4,4-dimethylthreonine cyclosporin A