BIRD-PRD_000768: CYCLOSPORIN A, 8 mutation

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000768
• Status: Status: REF ONLY
• Name: CYCLOSPORIN A, 8 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 A MOLECULE WAS MODIFIED AT POSITION 8 TO BE N-METHYL-ISOLEUCINE

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• 4 MEILE CYCLOSPORIN (PDB)

Annotation

• Function: Inhibitor of PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A, EC: 5.2.1.8EC: Inhibitor of PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A, EC: 5.2.1.8 / Info source: PubMed: 9769216

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: C₆₂H₁₁₁N₁₁O₁₂ / Formula weight: 1202.611

• 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)CC(C)C)CC(C)C)C)C)CC(C)C)C)C(C)C)C(C)CC
• CACTVS 3.370: CC[CH](C)[CH]1N(C)C(=O)CN(C)C(=O)[CH](CC)NC(=O)[CH]([CH](O)[CH](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](NC1=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)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)C(C)CC)C)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@@H]1N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=O)[C@H]([C@H](O)[C@H](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](NC1=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@H](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)[C@@H](C)CC)C)C

InChI

• InChI 1.03: InChI=1S/C62H111N11O12/c1-25-28-29-40(15)52(75)51-56(79)65-43(27-3)58(81)67(18)33-47(74)71(22)50(39(14)26-2)55(78)66-48(37(10)11)61(84)68(19)44(30-34(4)5)54(77)63-41(16)53(76)64-42(17)57(80)69(20)45(31-35(6)7)59(82)70(21)46(32-36(8)9)60(83)72(23)49(38(12)13)62(85)73(51)24/h25,28,34-46,48-52,75H,26-27,29-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b28-25-/t39-,40-,41+,42+,43+,44+,45+,46-,48-,49+,50+,51-,52+/m0/s1

InChIKey

• InChI 1.03: RPJPZDVUUKWPGT-DXQKFWBWSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (3R,6S,9R,12R,15R,18R,21S,24R,30R,33S)-24-[(2S)-butan-2-yl]-30-ethyl-33-[(1R,2S,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18-tris(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)-24-[(2S)-butan-2-yl]-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-33-[(E,1R,2R)-2-methyl-1-oxidanyl-hex-4-enyl]-6,9,18-tris(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 1 items

PDB-1cwm:
HUMAN CYCLOPHILIN A COMPLEXED WITH 4 MEILE CYCLOSPORIN