Omphalotin-A
General
Type : Peptide || Natural || Macrolide || Antibiotic
Chemical_Nomenclature : (3S,6S,9S,12S,15S,21S,24S,30S,33S)-9,21,30-tris[(2S)-butan-2-yl]-15-(1H-indol-3-ylmethyl)-1,4,7,13,19,22,28,31,34-nonamethyl-3,6,12,24,33-penta(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31,34-dodecazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
Canonical SMILES : CCC(C)C1C(=O)N(C(C(=O)N(C(C(=O)N(CC(=O)N(C(C(=O)N(C(C(=O)N(CC(=O)NC(C(=O)N(C(C(=O)N(CC(=O)NC(C(=O)N(C(C(=O)N1)C(C)C)C)CC2=CNC3 =CC=CC=C32)C)C(C)CC)C)C(C)C)C)C(C)CC)C)C(C)C)C)C)C(C)C)C)C(C)C)C
InChI : InChI=1S\/C69H115N13O12\/c1-26-43(14)54-64(89)79(22)58(42(12)13)69(94)80(23)56(40(8)9)65(90)76(19)37-52(85)77(20)57(41(10)11)68(93)82(25)60(45(16)28-3) 67(92)75(18)36-51(84)72-53(38(4)5)63(88)81(24)59(44(15)27-2)66(91)74(17)35-50(83)71-49(33-46-34-70-48-32-30-29-31-47(46)48)62(87)78(21)55(39(6)7)61(86) 73-54\/h29-32,34,38-45,49,53-60,70H,26-28,33,35-37H2,1-25H3,(H,71,83)(H,72,84)(H,73,86)\/t43-,44-,45-,49-,53-,54-,55-,56-,57-,58-,59-,60-\/m0\/s1
InChIKey : RPRXGEAIZUOLRT-SNXGSGAFSA-N
Other name(s) : Omphalotin, Omphalotin A, CHEMBL4212984, cyclo[Sar-Trp-N(Me)Val-Ile-N(Me)Val-N(Me)Val-Sar-N(Me)Val-N(Me)Ile-Sar-Val-N(Me)Ile], cyclo[sarcosyl-L-tryptophyl-N-methyl-L-valyl-L-isoleucyl-N-methyl-L-valyl-N-methyl-L-valyl-sarcosyl-N-methyl-L-valyl-N-methyl-L-isoleucyl-sarcosyl-L-valyl-N-methyl-L-isoleucyl]
Target
Families : S9N_PPCE_Peptidase_S9
References (3)
| Title : Identification, heterologous production and bioactivity of lentinulin A and dendrothelin A, two natural variants of backbone N-methylated peptide macrocycle omphalotin A - Matabaro_2021_Sci.Rep_11_3541 |
| Author(s) : Matabaro E , Kaspar H , Dahlin P , Bader DLV , Murar CE , Staubli F , Field CM , Bode JW , Kunzler M |
| Ref : Sci Rep , 11 :3541 , 2021 |
| Abstract : Matabaro_2021_Sci.Rep_11_3541 |
| ESTHER : Matabaro_2021_Sci.Rep_11_3541 |
| PubMedSearch : Matabaro_2021_Sci.Rep_11_3541 |
| PubMedID: 33574430 |
| Gene_locus related to this paper: ompol-OphP |
| Title : Expanding the Structural Space of Ribosomal Peptides: Autocatalytic N-Methylation in Omphalotin Biosynthesis - Aldemir_2017_Angew.Chem.Int.Ed.Engl_56_13570 |
| Author(s) : Aldemir H , Gulder TAM |
| Ref : Angew Chem Int Ed Engl , 56 :13570 , 2017 |
| Abstract : Aldemir_2017_Angew.Chem.Int.Ed.Engl_56_13570 |
| ESTHER : Aldemir_2017_Angew.Chem.Int.Ed.Engl_56_13570 |
| PubMedSearch : Aldemir_2017_Angew.Chem.Int.Ed.Engl_56_13570 |
| PubMedID: 28949431 |
| Title : A Self-Sacrificing N-Methyltransferase Is the Precursor of the Fungal Natural Product Omphalotin - Ramm_2017_Angew.Chem.Int.Ed.Engl_56_9994 |
| Author(s) : Ramm S , Krawczyk B , Muhlenweg A , Poch A , Mosker E , Sussmuth RD |
| Ref : Angew Chem Int Ed Engl , 56 :9994 , 2017 |
| Abstract : Ramm_2017_Angew.Chem.Int.Ed.Engl_56_9994 |
| ESTHER : Ramm_2017_Angew.Chem.Int.Ed.Engl_56_9994 |
| PubMedSearch : Ramm_2017_Angew.Chem.Int.Ed.Engl_56_9994 |
| PubMedID: 28715095 |
| Gene_locus related to this paper: ompol-OphP |