PRD_000203
Summary
| Name: | Chloroorienticin A |
| Formula: | C73 H88 Cl2 N10 O26 |
| Fomular weight: | 1592.437 |
| Component type: | peptide-like |
| Polymer sequences: | MLU, OMZ, ASN, GHP, GHP, OMY, 3FG |
| Non-polymer components: | |
| BIRD class: | Antibiotic |
| Represented as: | polymer |
| Compound Details: | CHLOROORIENTICIN A IS A TRICYCLIC GLYCOPEPTIDE, A MEMBER OF THE VANCOMYCIN FAMILY. THE SCAFFOLD IS A HEPTAPEPTIDE WITH THE CONFIGURATION D-D-L-D-D-L-L. IT IS FURTHER GLYCOSYLATED BY ONE DISACCHARIDE AND ONE MONOSACCHARIDE HERE, CHLOROORIENTICIN A IS REPRESENTED BY GROUPING TOGETHER THE SEQUENCE (SEQRES) AND THE THREE LIGANDS (HET) BGC AND TWO RER. |
| Description: | CHLOROORIENTICIN A IS A TRICYCLIC GLYCOPEPTIDE, GLYCOSYLATED BY ONE DISACCHARIDE ON RESIDUE 4 AND ONE MONOSACCHARIDE ON RESIDUE 6. |
| Families: | FAM_000087 |
| Program | Version | Name |
| ACDLabs | 12.01 | (1S,2R,18R,19R,22S,25R,28R,40S)-2-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-22-(2-amino-2-oxoethyl)-5,15-dichloro-18,32,35,37-tetrahydroxy-19-{[(2R)-4-methyl-2-(methylamino)pentanoyl]amino}-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2~3,6~.2~14,17~.1~8,12~.1~29,33~.0~10,25~.0~34,39~]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid (non-preferred name) |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=C3NC(C(=O)O)c1cc(O)cc(O)c1c2c(O)ccc(c2)C%10C(=O)NC3C(OC4OC(C(O)C(N)(C4)C)C)c%11ccc(Oc9c(OC6OC(CO)C(O)C(O)C6OC5OC(C)C(O)C(N)(C)C5)c8Oc7ccc(cc7Cl)C(O)C(NC(=O)C(NC)CC(C)C)C(=O)NC(C(=O)NC(c(c8)c9)C(=O)N%10)CC(=O)N)c(Cl)c%11 |
| InChI | InChI | 1.03 | InChI=1S/C73H88Cl2N10O26/c1-26(2)14-38(79-7)64(96)84-54-56(91)30-9-12-42(36(74)16-30)106-44-18-32-19-45(60(44)111-71-61(58(93)57(92)46(25-86)108-71)110-49-24-73(6,78)63(95)28(4)105-49)107-43-13-10-31(17-37(43)75)59(109-48-23-72(5,77)62(94)27(3)104-48)55-69(101)83-53(70(102)103)35-20-33(87)21-41(89)50(35)34-15-29(8-11-40(34)88)51(66(98)85-55)82-67(99)52(32)81-65(97)39(22-47(76)90)80-68(54)100/h8-13,15-21,26-28,38-39,46,48-49,51-59,61-63,71,79,86-89,91-95H,14,22-25,77-78H2,1-7H3,(H2,76,90)(H,80,100)(H,81,97)(H,82,99)(H,83,101)(H,84,96)(H,85,98)(H,102,103)/t27-,28-,38+,39-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1 |
| InChIKey | InChI | 1.03 | XJHXLMVKYIVZTE-LOALFDMRSA-N |
| SMILES_CANONICAL | CACTVS | 3.370 | CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O[C@H]6C[C@](C)(N)[C@@H](O)[C@H](C)O6)[C@@H]7NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c8ccc(O)c(c8)c9c(O)cc(O)cc9[C@H](NC7=O)C(O)=O)c3O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%10O[C@H]%11C[C@](C)(N)[C@@H](O)[C@H](C)O%11)c(Cl)c2 |
| SMILES | CACTVS | 3.370 | CN[CH](CC(C)C)C(=O)N[CH]1[CH](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[CH](O[CH]6C[C](C)(N)[CH](O)[CH](C)O6)[CH]7NC(=O)[CH](NC(=O)[CH]4NC(=O)[CH](CC(N)=O)NC1=O)c8ccc(O)c(c8)c9c(O)cc(O)cc9[CH](NC7=O)C(O)=O)c3O[CH]%10O[CH](CO)[CH](O)[CH](O)[CH]%10O[CH]%11C[C](C)(N)[CH](O)[CH](C)O%11)c(Cl)c2 |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | C[C@H]1[C@@H]([C@@](C[C@@H](O1)O[C@@H]2c3ccc(c(c3)Cl)Oc4cc5cc(c4O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7C[C@]([C@H]([C@@H](O7)C)O)(C)N)Oc8ccc(cc8Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]9c1ccc(c(c1)-c1c(cc(cc1O)O)[C@H](NC(=O)[C@H]2NC9=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)(C)N)O |
| SMILES | OpenEye OEToolkits | 1.7.6 | CC1C(C(CC(O1)OC2c3ccc(c(c3)Cl)Oc4cc5cc(c4OC6C(C(C(C(O6)CO)O)O)OC7CC(C(C(O7)C)O)(C)N)Oc8ccc(cc8Cl)C(C(C(=O)NC(C(=O)NC5C(=O)NC9c1ccc(c(c1)-c1c(cc(cc1O)O)C(NC(=O)C2NC9=O)C(=O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)(C)N)O |
