PRD_000217
Summary
| Name: | Daptomycin |
| Formula: | C72 H101 N17 O26 |
| Fomular weight: | 1620.671 |
| Component type: | peptide-like |
| Polymer sequences: | TRP, DSG, ASP, THR, GLY, ORN, ASP, DAL, ASP, GLY, DSN, LME, KYN |
| Non-polymer components: | |
| BIRD class: | Antibiotic |
| Represented as: | polymer |
| Compound Details: | DAPTOMYCIN IS A CYCLIC TRIDECAMER LIPOPETIDE. HERE, DAPTOMYCIN IS REPRESENTED BY GROUPING TOGETHER THE SEQUENCE (SEQRES) AND ONE LIGAND (HET) DKA. |
| Description: | DAPTOMYCIN IS AN ACIDIC CYCLIC LIPOPEPTIDE. THE SCAFFOLD IS MADE OF TWO PARTS: (1) THREE RESIDUES N-TERM EXOCYCLIC PART (2) A DECAPEPTIDE LACTONE RING DERIVED FROM CYCLISATION OF THR3 SIDE CHAIN ONTO THE C-TER CARBOXYL GROUP THE N-DECANOYL FATTY ACID IS LINKED TO THE MAIN BODY OF THE MOLECULE VIA N-TERM ACYLATION. |
| Program | Version | Name |
| ACDLabs | 12.01 | N-decanoyl-L-tryptophyl-L-asparaginyl-N-[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]-L-alpha-asparagine |
| OpenEye OEToolkits | 1.7.6 | (3S)-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxidanylidene-ethyl]-24-(3-azanylpropyl)-9-(hydroxymethyl)-15,21-bis(2-hydroxy-2-oxoethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decakis(oxidanylidene)-6-[(2R)-4-oxidanyl-4-oxidanylidene-butan-2-yl]-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-3-[[(2S)-4-azanyl-2-[[(2S)-2-(decanoylamino)-3-(1H-indol-3-yl)propanoyl]amino]-4-oxidanylidene-butanoyl]amino]-4-oxidanylidene-butanoic acid |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=C(NC(C(=O)NC(C(=O)NC(C(=O)NC1C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)OC1C)CC(=O)c2ccccc2N)C(C)CC(=O)O)CO)CC(=O)O)C)CC(=O)O)CCCN)CC(=O)O)CC(=O)N)Cc3cnc4ccccc34)CCCCCCCCC |
| InChI | InChI | 1.03 | InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1 |
| InChIKey | InChI | 1.03 | DOAKLVKFURWEDJ-RWDRXURGSA-N |
| SMILES_CANONICAL | CACTVS | 3.370 | CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H]3[C@@H](C)OC(=O)[C@H](CC(=O)c4ccccc4N)NC(=O)[C@@H](NC(=O)[C@@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN)NC(=O)CNC3=O)[C@H](C)CC(O)=O |
| SMILES | CACTVS | 3.370 | CCCCCCCCCC(=O)N[CH](Cc1c[nH]c2ccccc12)C(=O)N[CH](CC(N)=O)C(=O)N[CH](CC(O)=O)C(=O)N[CH]3[CH](C)OC(=O)[CH](CC(=O)c4ccccc4N)NC(=O)[CH](NC(=O)[CH](CO)NC(=O)CNC(=O)[CH](CC(O)=O)NC(=O)[CH](C)NC(=O)[CH](CC(O)=O)NC(=O)[CH](CCCN)NC(=O)CNC3=O)[CH](C)CC(O)=O |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]3[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)c4ccccc4N)C |
| SMILES | OpenEye OEToolkits | 1.7.6 | CCCCCCCCCC(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)c4ccccc4N)C |
