PRD_000199
Summary
| Name: | Mersacidin |
| Formula: | C80 H120 N20 O21 S4 |
| Fomular weight: | 1826.19 |
| Component type: | peptide-like |
| Polymer sequences: | CYS, DBB, PHE, DBB, LEU, PRO, GLY, GLY, GLY, GLY, VAL, CYS, DBB, LEU, DBB, DHA, GLU, CYS, ILE, TEE |
| Non-polymer components: | |
| BIRD class: | Antibiotic |
| Represented as: | polymer |
| Compound Details: | MERSACIDIN IS A GLOBULAR TYPE B LANTIBIOTIC. THE LANTIBIOTICS ARE CHARACTERIZED BY THIOETHER AMINO ACIDS LANTHIONINE AND/OR METHYLLANTHIONINE. HERE, MERSACIDIN IS REPRESENTED BY THE SEQUENCE (SEQRES) |
| Description: | MERSACIDIN IS A TETRACYCLIC PEPTIDE. POST TRANSLATIONAL MATURATION OF LANTIBIOTICS INVOLVES THE ENZYMIC CONVERSION OF THR, AND SER INTO DEHYDRATED AA AND THE FORMATION OF THIOETHER BONDS WITH CYSTEINE. THE CARBOXY-TERMINAL BETA-METHYLLANTHIONINE UNDERGOES DECARBOXYLATION. THIOETHER BONDS WITH CYSTEINE RESULT IN FOUR RINGS. THIS IS FOLLOWED BY MEMBRANE TRANSLOCATION AND CLEAVAGE OF THE MODIFIED PRECURSOR. |
| Families: | FAM_000084 |
| Program | Version | Name |
| ACDLabs | 12.01 | 3-[(1R,4S,7S,8S,11R,14S,17Z,20R,26S)-7-({[(15R,18R,21R,22R,25R,30aS)-22-[(N-{[(2S,3S,6R)-6-amino-2-methyl-5-oxo-1,4-thiazepan-3-yl]carbonyl}-L-phenylalanyl)amino]-21-methyl-25-(2-methylpropyl)-1,4,7,10,13,16,23,26-octaoxo-15-(propan-2-yl)octacosahydro-1H-pyrrolo[2,1-u][1,4,7,10,13,16,19,22,25]thiaoctaazacyclooctacosin-18-yl]carbonyl}amino)-14-[(2R)-butan-2-yl]-8,20-dimethyl-23-methylidene-4-(2-methylpropyl)-3,6,12,15,21,24,27-heptaoxo-9,19-dithia-2,5,13,16,22,25,28-heptaazabicyclo[9.9.8]octacos-17-en-26-yl]propanoic acid |
| OpenEye OEToolkits | 1.7.6 | 3-[(1R,4S,7Z,11S,14S,17S,23S)-17-[[(3S,6S,10R,13S,28S)-6-[[(2S)-2-[[(3S,6R)-6-azanyl-2-methyl-5-oxidanylidene-1,4-thiazepan-3-yl]carbonylamino]-3-phenyl-propanoyl]amino]-7-methyl-3-(2-methylpropyl)-2,5,12,15,18,21,24,27-octakis(oxidanylidene)-13-propan-2-yl-8-thia-1,4,11,14,17,20,23,26-octazabicyclo[26.3.0]hentriacontan-10-yl]carbonylamino]-4-[(2S)-butan-2-yl]-10,18-dimethyl-26-methylidene-14-(2-methylpropyl)-2,5,13,16,22,25,28-heptakis(oxidanylidene)-9,19-dithia-3,6,12,15,21,24,27-heptazabicyclo[9.9.8]octacos-7-en-23-yl]propanoic acid |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=C6NC(C(=O)N1CCCC1C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)NC3C(=O)NC(C(=O)NC2C(=O)NC(/C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC=CSC2C)C(C)CC)CSC3C)CCC(=O)O)=C)CC(C)C)CSC(C)C6NC(=O)C(NC(=O)C4NC(=O)C(N)CSC4C)Cc5ccccc5)C(C)C)CC(C)C |
| InChI | InChI | 1.03 | InChI=1S/C80H120N20O21S4/c1-14-40(8)61-74(115)82-24-26-122-42(10)62-76(117)87-41(9)66(107)88-48(22-23-59(105)106)68(109)92-52(71(112)95-61)35-124-44(12)64(78(119)89-49(27-37(2)3)69(110)97-62)99-72(113)53-36-125-45(13)65(98-70(111)50(29-46-19-16-15-17-20-46)90-77(118)63-43(11)123-34-47(81)67(108)96-63)79(120)91-51(28-38(4)5)80(121)100-25-18-21-54(100)73(114)86-32-57(103)84-30-55(101)83-31-56(102)85-33-58(104)94-60(39(6)7)75(116)93-53/h15-17,19-20,24,26,37-40,42-45,47-54,60-65H,9,14,18,21-23,25,27-36,81H2,1-8,10-13H3,(H,82,115)(H,83,101)(H,84,103)(H,85,102)(H,86,114)(H,87,117)(H,88,107)(H,89,119)(H,90,118)(H,91,120)(H,92,109)(H,93,116)(H,94,104)(H,95,112)(H,96,108)(H,97,110)(H,98,111)(H,99,113)(H,105,106)/b26-24+/t40-,42?,43+,44+,45-,47+,48+,49+,50+,51-,52+,53+,54+,60+,61+,62+,63-,64-,65-/m1/s1 |
| InChIKey | InChI | 1.03 | JSWKNDSDVHJUKY-HJEDKZKVSA-N |
| SMILES_CANONICAL | CACTVS | 3.370 | CC[C@H](C)[C@@H]1NC(=O)[C@@H]2CS[C@@H](C)[C@@H](NC(=O)[C@@H]3CS[C@@H](C)[C@@H](NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H]5NC(=O)[C@@H](N)CS[C@H]5C)C(=O)N[C@@H](CC(C)C)C(=O)N6CCC[C@H]6C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N3)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]([C@H](C)S\C=C/NC1=O)C(=O)NC(=C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2 |
| SMILES | CACTVS | 3.370 | CC[CH](C)[CH]1NC(=O)[CH]2CS[CH](C)[CH](NC(=O)[CH]3CS[CH](C)[CH](NC(=O)[CH](Cc4ccccc4)NC(=O)[CH]5NC(=O)[CH](N)CS[CH]5C)C(=O)N[CH](CC(C)C)C(=O)N6CCC[CH]6C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[CH](C(C)C)C(=O)N3)C(=O)N[CH](CC(C)C)C(=O)N[CH]([CH](C)SC=CNC1=O)C(=O)NC(=C)C(=O)N[CH](CCC(O)=O)C(=O)N2 |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | CC[C@H](C)[C@H]1C(=O)N/C=C\SC([C@@H]2C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@@H](CSC([C@H](C(=O)N[C@H](C(=O)N2)CC(C)C)NC(=O)[C@@H]3CSC([C@H](C(=O)N[C@H](C(=O)N4CCC[C@H]4C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)N3)C(C)C)CC(C)C)NC(=O)[C@H](Cc5ccccc5)NC(=O)[C@H]6C(SC[C@@H](C(=O)N6)N)C)C)C)C(=O)N1)CCC(=O)O)C |
| SMILES | OpenEye OEToolkits | 1.7.6 | CCC(C)C1C(=O)NC=CSC(C2C(=O)NC(=C)C(=O)NC(C(=O)NC(CSC(C(C(=O)NC(C(=O)N2)CC(C)C)NC(=O)C3CSC(C(C(=O)NC(C(=O)N4CCCC4C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)NC(C(=O)N3)C(C)C)CC(C)C)NC(=O)C(Cc5ccccc5)NC(=O)C6C(SCC(C(=O)N6)N)C)C)C)C(=O)N1)CCC(=O)O)C |
