GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

ubonodin   Click here for help

GtoPdb Ligand ID: 14235

Compound class: Peptide
Comment: Ubonodin is an antimicrobial lasso peptide discovered using genome mining in Burkholderia ubonensis [1]. It inhibits bacterial RNA polymerase in vitro and has activity against B. multivorans and B. cepacia, opportunistic bacterial pathogens that can cause lung infections in cystic fibrosis patients.
2D Structure
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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/)

✖
Canonical SMILES CC[C@H](C)[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)NCC(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N1)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC5=CNC=N5)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC6=CNC=N6)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC7=CNC8=C7C=CC=C8)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC9=CC=C(C=C9)O)C(=O)N[C@@H](CC%10=CC=C(C=C%10)O)C(=O)NCC(=O)O
Isomeric SMILES CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)CO)CC(=O)O)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC5=CNC=N5)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC6=CNC=N6)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC9=CC=C(C=C9)O)C(=O)N[C@@H](CC%10=CC=C(C=C%10)O)C(=O)NCC(=O)O)C
InChI InChI=1S/C143H196N38O43S2/c1-10-71(4)117-139(221)159-74(7)120(202)163-88(39-41-108(189)152-62-109(190)153-63-110(191)161-100(56-113(194)195)122(204)154-65-112(193)162-104(68-183)137(219)180-117)124(206)169-95(51-78-30-36-84(186)37-31-78)129(211)170-94(48-75-20-14-13-15-21-75)130(212)173-99(55-107(145)188)133(215)167-91(24-18-44-150-143(146)147)142(224)181-45-19-25-105(181)138(220)165-89(42-46-225-8)125(207)172-98(54-81-61-149-70-158-81)136(218)179-119(73(6)12-3)141(223)176-97(53-80-60-148-69-157-80)132(214)175-101(57-114(196)197)134(216)171-96(52-79-59-151-86-23-17-16-22-85(79)86)131(213)164-87(38-40-106(144)187)127(209)178-118(72(5)11-2)140(222)166-90(43-47-226-9)126(208)174-102(58-115(198)199)135(217)177-103(67-182)123(205)155-64-111(192)160-93(50-77-28-34-83(185)35-29-77)128(210)168-92(121(203)156-66-116(200)201)49-76-26-32-82(184)33-27-76/h13-17,20-23,26-37,59-61,69-74,87-105,117-119,151,182-186H,10-12,18-19,24-25,38-58,62-68H2,1-9H3,(H2,144,187)(H2,145,188)(H,148,157)(H,149,158)(H,152,189)(H,153,190)(H,154,204)(H,155,205)(H,156,203)(H,159,221)(H,160,192)(H,161,191)(H,162,193)(H,163,202)(H,164,213)(H,165,220)(H,166,222)(H,167,215)(H,168,210)(H,169,206)(H,170,211)(H,171,216)(H,172,207)(H,173,212)(H,174,208)(H,175,214)(H,176,223)(H,177,217)(H,178,209)(H,179,218)(H,180,219)(H,194,195)(H,196,197)(H,198,199)(H,200,201)(H4,146,147,150)/t71-,72-,73-,74-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,117-,118-,119-/m0/s1
InChI Key AELLOIFPDIOLRK-KHQMEOLFSA-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
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ubonodin
Other databases
ChEMBL Ligand CHEMBL5439950
PubChem CID 172470956
Search Google for chemical match using the InChIKey AELLOIFPDIOLRK-KHQMEOLFSA-N
Search Google for chemicals with the same backbone AELLOIFPDIOLRK
UniChem Compound Search for chemical match using the InChIKey AELLOIFPDIOLRK-KHQMEOLFSA-N
UniChem Connectivity Search for chemical match using the InChIKey AELLOIFPDIOLRK-KHQMEOLFSA-N