BIRD-PRD_000186: EFRAPEPTIN C

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000186
• Status: Status: REF ONLY
• Name: EFRAPEPTIN C

BIRD information

• Type: Polypeptide / Antimicrobial

Details

• EFRAPEPTIN C IS A MEMBER OF CLOSELY RELATED LINEAR AMPHIPHILIC PEPTIDE ANTIBIOTICS. MEMBERS OF THIS FAMILY HAVE AN ACETYLATED PIPECOLIC AT THE N-TERM AND AT THE C-TERM A MODIFIED LEUCINE WITH AN ATTACHED HETEROCYCLIC RING STRUCTURE. HERE, EFRAPEPTIN C IS REPRESENTED BY THE SEQUENCE (SEQRES)
• EFRAPEPTIN C IS A LINEAR PEPTIDE, WITH ACETYLATED (ACE) PIPECOLIC ACID (YCP) AT THE N-TERMINUS AND A MODIFIED LEUCINE AT THE C-TERM (TLX)

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• 14-[N-[1-[(2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium-1-yl)methyl]-3-methylbutyl]-2-methylalaninamide]-, (S)- (SciFinder)
• EFRAPEPTIN (PDB)
• Efrapeptin C (9CI) (SciFinder)
• Efrapeptin D (SciFinder)
• Pyrrolo[1,2-a]pyrimidine, efrapeptin D deriv. (SciFinder)

Annotation

• Function: inhibits both ATP synthesis and hydrolysis by binding to the F1 catalytic domain of F1F0-ATP synthase / Info source: PubMed: 8790345

Source

• Tolypocladium niveum, :

External info

• CAS: 138145-54-7
• [MESH_Unique_ID] MESH: C012953

Family

EFRAPEPTIN

EFRAPEPTIN C

Chemical information

Composition

Formula: C₈₀H₁₃₈N₁₈O₁₆ / Formula weight: 1608.063

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(N1CCCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCC(=O)NCC(=O)NC(C(=O)NC(C(=O)N2CCCCC2C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(CC(C)C)CN4CCCN3CCCC34)(C)C)CC(C)C)(C)C)(C)C)(C)C)CC(C)C)(C)C)(C)C)C(NC(=O)C5N(C(=O)C)CCCC5)(C)C
• CACTVS 3.370: CC(C)C[CH](CN1CCCN2CCC[CH]12)NC(=O)C(C)(C)NC(=O)[CH](CC(C)C)NC(=O)CNC(=O)C(C)(C)NC(=O)[CH]3CCCCN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)CCNC(=O)[CH](CC(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)[CH]4CCCCN4C(=O)C(C)(C)NC(=O)[CH]5CCCCN5C(C)=O
• OpenEye OEToolkits 1.7.6: CC(C)CC(CN1CCCN2C1CCC2)NC(=O)C(C)(C)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(C)(C)NC(=O)C3CCCCN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)CCNC(=O)C(CC(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C4CCCCN4C(=O)C(C)(C)NC(=O)C5CCCCN5C(=O)C

SMILES CANONICAL

• CACTVS 3.370: CC(C)C[C@@H](CN1CCCN2CCC[C@@H]12)NC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H]3CCCCN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)CCNC(=O)[C@H](CC(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)[C@@H]4CCCCN4C(=O)C(C)(C)NC(=O)[C@@H]5CCCCN5C(C)=O
• OpenEye OEToolkits 1.7.6: CC(C)C[C@@H](CN1CCCN2[C@H]1CCC2)NC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H]3CCCCN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)CCNC(=O)[C@H](CC(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)[C@@H]4CCCCN4C(=O)C(C)(C)NC(=O)[C@@H]5CCCCN5C(=O)C

InChI

• InChI 1.03: InChI=1S/C80H138N18O16/c1-48(2)42-52(47-95-38-29-37-94-36-28-33-61(94)95)84-68(109)75(10,11)88-63(104)54(44-50(5)6)85-59(101)45-83-67(108)74(8,9)89-65(106)56-31-24-27-41-98(56)73(114)80(20,21)93-70(111)77(14,15)87-60(102)46-82-58(100)34-35-81-62(103)53(43-49(3)4)86-69(110)76(12,13)92-71(112)78(16,17)90-66(107)57-32-23-26-40-97(57)72(113)79(18,19)91-64(105)55-30-22-25-39-96(55)51(7)99/h48-50,52-57,61H,22-47H2,1-21H3,(H,81,103)(H,82,100)(H,83,108)(H,84,109)(H,85,101)(H,86,110)(H,87,102)(H,88,104)(H,89,106)(H,90,107)(H,91,105)(H,92,112)(H,93,111)

InChIKey

• InChI 1.03: GTIBOEWQVGCNQF-UHFFFAOYSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: There are more than 8 acyclic senior suffix groups!
• OpenEye OEToolkits 1.7.6: (2S)-N-[1-[(2S)-2-[[1-[[1-[[(2S)-1-[[3-[[2-[[1-[[1-[(2S)-2-[[1-[[2-[[(2S)-1-[[1-[[(2S)-1-[(8aR)-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[1,2-a]pyrimidin-1-yl]-4-methyl-pentan-2-yl]amino]-2-methyl-1-oxidanylidene-propan-2-yl]amino]-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-2-oxidanylidene-ethyl]amino]-2-methyl-1-oxidanylidene-propan-2-yl]carbamoyl]piperidin-1-yl]-2-methyl-1-oxidanylidene-propan-2-yl]amino]-2-methyl-1-oxidanylidene-propan-2-yl]amino]-2-oxidanylidene-ethyl]amino]-3-oxidanylidene-propyl]amino]-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-2-methyl-1-oxidanylidene-propan-2-yl]amino]-2-methyl-1-oxidanylidene-propan-2-yl]carbamoyl]piperidin-1-yl]-2-methyl-1-oxidanylidene-propan-2-yl]-1-ethanoyl-piperidine-2-carboxamide

PDB entries

Showing all 1 items

PDB-1efr:
BOVINE MITOCHONDRIAL F1-ATPASE COMPLEXED WITH THE PEPTIDE ANTIBIOTIC EFRAPEPTIN