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ramoplanin A2   Click here for help

GtoPdb Ligand ID: 14348

Synonyms: A-16686A2 | MDL 62,198
Compound class: Peptide
Comment: Ramoplanin is a glycolipodepsipeptide antibacterial with Gram-positive activity, originally isolated from the culture broth of Actinoplanes strain ATCC 33076 as a mixture of three components (ramoplanin A1, A2, and A3) [1,3].
We show the structure for ramoplanin A2 which is the major component. Note that the INN describes the mixture. As with other natural products, there is ambiguity in the precise stereochemisrty presented across web resources e.g., CHEMBL3989605 shows an alternate structure.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(C)C/C=C/C=C\C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H]1[C@@H](C(=O)N)OC(=O)[C@H](C2=CC=C(C(=C2)Cl)O)NC(=O)[C@@H](C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C3=CC=C(C=C3)O)NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@H](C4=CC=C(C=C4)O[C@@H]5[C@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@@H]6[C@H]([C@H]([C@@H]([C@@H](CO)O6)O)O)O)NC(=O)[C@@H](CCCN)NC(=O)[C@H](CC7=CC=CC=C7)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@@H](C8=CC=C(C=C8)O)NC(=O)[C@H](C9=CC=C(C=C9)O)NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@@H](CCCN)NC(=O)[C@@H](C%10=CC=C(C=C%10)O)NC1=O
Isomeric SMILES C[C@@H]1C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)CC(C)C)C2=CC=C(C=C2)O)[C@@H](C)O)C3=CC=C(C=C3)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CCCN)CC6=CC=CC=C6)[C@H](C)O)C7=CC=C(C=C7)O)C8=CC=C(C=C8)O)[C@@H](C)O)CCCN)C9=CC=C(C=C9)O)NC(=O)[C@H](CC(=O)N)NC(=O)/C=C\C=C\CC(C)C)C(=O)N)C%10=CC(=C(C=C%10)O)Cl
InChI InChI=1S/C119H154ClN21O40/c1-54(2)17-11-9-14-22-82(153)127-77(50-81(123)152)107(166)141-93-99(101(124)160)180-117(176)92(66-33-44-78(151)72(120)49-66)140-102(161)56(5)126-105(164)75(47-55(3)4)128-83(154)51-125-108(167)87(61-23-34-67(147)35-24-61)136-111(170)86(59(8)146)134-113(172)89(65-31-42-71(43-32-65)177-119-100(97(158)95(156)80(53-143)179-119)181-118-98(159)96(157)94(155)79(52-142)178-118)135-104(163)73(20-15-45-121)129-106(165)76(48-60-18-12-10-13-19-60)131-109(168)84(57(6)144)133-114(173)90(63-27-38-69(149)39-28-63)138-115(174)91(64-29-40-70(150)41-30-64)137-110(169)85(58(7)145)132-103(162)74(21-16-46-122)130-112(171)88(139-116(93)175)62-25-36-68(148)37-26-62/h9-14,18-19,22-44,49,54-59,73-77,79-80,84-100,118-119,142-151,155-159H,15-17,20-21,45-48,50-53,121-122H2,1-8H3,(H2,123,152)(H2,124,160)(H,125,167)(H,126,164)(H,127,153)(H,128,154)(H,129,165)(H,130,171)(H,131,168)(H,132,162)(H,133,173)(H,134,172)(H,135,163)(H,136,170)(H,137,169)(H,138,174)(H,139,175)(H,140,161)(H,141,166)/b11-9+,22-14-/t56-,57+,58-,59-,73-,74-,75+,76+,77+,79-,80-,84+,85-,86-,87+,88-,89+,90-,91+,92+,93+,94-,95-,96+,97+,98+,99+,100+,118-,119+/m1/s1
InChI Key KGZHFKDNSAEOJX-WIFQYKSHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Peptide
International Nonproprietary Names Click here for help
INN number INN
6115 ramoplanin
Synonyms Click here for help
A-16686A2 | MDL 62,198
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ramoplanin
Other databases
CAS Registry No. 81988-88-7 (source: Scifinder)
ChEBI CHEBI:29670
DrugBank Ligand DB04952
GtoPdb PubChem SID 523352140
PubChem CID 16129628
Search Google for chemical match using the InChIKey KGZHFKDNSAEOJX-WIFQYKSHSA-N
Search Google for chemicals with the same backbone KGZHFKDNSAEOJX
Search PubMed clinical trials ramoplanin
Search PubMed titles ramoplanin
Search PubMed titles/abstracts ramoplanin
UniChem Compound Search for chemical match using the InChIKey KGZHFKDNSAEOJX-WIFQYKSHSA-N
UniChem Connectivity Search for chemical match using the InChIKey KGZHFKDNSAEOJX-WIFQYKSHSA-N