PRD_000195
Summary
| Name: | Cinnamycin |
| Formula: | C89 H127 N25 O25 S3 |
| Fomular weight: | 2043.308 |
| Component type: | peptide-like |
| Polymer sequences: | CYS, ARG, GLN, DAL, CYS, SER, PHE, GLY, PRO, PHE, DBB, PHE, VAL, CYS, BH2, GLY, ASN, DBB, LYS |
| Non-polymer components: | |
| BIRD class: | Lantibiotic |
| Represented as: | polymer |
| Compound Details: | CINNAMYCIN IS A GLOBULAR TYPE B LANTIBIOTIC. THE LANTIBIOTICS ARE CHARACTERIZED BY THIOESTER AMINO ACIDS LANTHIONINE AND/OR METHYLLANTHIONINE. HERE, CINNAMYCIN IS REPRESENTED BY THE SEQUENCE (SEQRES) |
| Description: | CINNAMYCIN IS A TETRACYCLIC PEPTIDE. POST TRANSLATIONAL MATURATION OF LANTIBIOTICS INVOLVES THE ENZYMIC CONVERSION OF THR AND SER INTO DEHYDRATED AMINO ACIDS AND THE FORMATION OF THIOETHER BONDS WITH CYSTEINE. THE 14-19 BETA-METHYLLANTHIONINE THIOETHER BOND IS OXIDIZED TO A SULFOXIDE. THE THIOETHER BONDS WITH CYSTEINE RESULT IN THREE RING STRUCTURES, CROSSLINK BETWEEN SER AND LYS RESULT IN THE FOURTH RING. THIS IS FOLLOWED BY MEMBRANE TRANSLOCATION AND CLEAVAGE OF THE MODIFIED PRECURSOR. |
| Families: | FAM_000084 |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| InChI | InChI | 1.03 | InChI=1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/p+2/t44-,45-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59-,60-,61-,66-,67+,68+,69-,70+/m0/s1 |
| InChIKey | InChI | 1.03 | QJDWKBINWOWJNZ-OURZNGJWSA-P |
| SMILES_CANONICAL | CACTVS | 3.370 | CC(C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]3NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H]5CCCN5C(=O)CNC(=O)[C@H](Cc6ccccc6)NC(=O)[C@@H]7C[NH2+]CCCC[C@H](NC(=O)[C@@H]8NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H](N)CS[C@H]8C)C(=O)N[C@@H](CS[C@H]3C)C(=O)N7)NC1=O)[C@@H](O)C(O)=O)C(O)=O |
| SMILES | CACTVS | 3.370 | CC(C)[CH]1NC(=O)[CH](Cc2ccccc2)NC(=O)[CH]3NC(=O)[CH](Cc4ccccc4)NC(=O)[CH]5CCCN5C(=O)CNC(=O)[CH](Cc6ccccc6)NC(=O)[CH]7C[NH2+]CCCC[CH](NC(=O)[CH]8NC(=O)[CH](CC(N)=O)NC(=O)CNC(=O)[CH](NC(=O)[CH](CSC[CH](NC(=O)[CH](CCC(N)=O)NC(=O)[CH](CCCNC(N)=[NH2+])NC(=O)[CH](N)CS[CH]8C)C(=O)N[CH](CS[CH]3C)C(=O)N7)NC1=O)[CH](O)C(O)=O)C(O)=O |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | CC1[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H]3CSC[C@@H]4C(=O)N[C@@H](CS1)C(=O)N[C@@H](C[NH2+]CCCC[C@H](NC(=O)[C@@H](C(SC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4)CCC(=O)N)CCCNC(=[NH2+])N)N)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC3=O)[C@H](C(=O)O)O)CC(=O)N)C(=O)O)C(=O)N[C@H](C(=O)NCC(=O)N5CCC[C@H]5C(=O)N[C@H](C(=O)N2)Cc6ccccc6)Cc7ccccc7)C(C)C)Cc8ccccc8 |
| SMILES | OpenEye OEToolkits | 1.7.6 | CC1C2C(=O)NC(C(=O)NC(C(=O)NC3CSCC4C(=O)NC(CS1)C(=O)NC(C[NH2+]CCCCC(NC(=O)C(C(SCC(C(=O)NC(C(=O)NC(C(=O)N4)CCC(=O)N)CCCNC(=[NH2+])N)N)C)NC(=O)C(NC(=O)CNC(=O)C(NC3=O)C(C(=O)O)O)CC(=O)N)C(=O)O)C(=O)NC(C(=O)NCC(=O)N5CCCC5C(=O)NC(C(=O)N2)Cc6ccccc6)Cc7ccccc7)C(C)C)Cc8ccccc8 |
