afabicin   Click here for help

GtoPdb Ligand ID: 10754

Synonyms: AFN-1720 | Debio 1450 | Debio1450
Compound class: Synthetic organic
Comment: Afabicin (DEBIO 1450) is an inhibitor of bacterial Fabl, the NADH-dependent enoyl reductase from the type II bacterial fatty acid biosynthesis pathway (FAS-II) [3]. This is a prodrug whose active metabolite is DEBIO 1452 (previously AFN-1252; PubChem CID: 10407120) [1].
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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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 143.22
Molecular weight 485.14
XLogP 0.53
No. Lipinski's rules broken 0
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.

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Canonical SMILES O=C(N(Cc1oc2c(c1C)cccc2)C)/C=C/c1cnc2c(c1)CCC(=O)N2COP(=O)(O)O
Isomeric SMILES O=C(N(Cc1oc2c(c1C)cccc2)C)/C=C/c1cnc2c(c1)CCC(=O)N2COP(=O)(O)O
InChI InChI=1S/C23H24N3O7P/c1-15-18-5-3-4-6-19(18)33-20(15)13-25(2)21(27)9-7-16-11-17-8-10-22(28)26(23(17)24-12-16)14-32-34(29,30)31/h3-7,9,11-12H,8,10,13-14H2,1-2H3,(H2,29,30,31)/b9-7+
InChI Key HFYMDQMXVPJNTH-VQHVLOKHSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form DEBIO 1452
IUPAC Name Click here for help
[6-[(E)-3-[methyl-[(3-methyl-1-benzofuran-2-yl)methyl]amino]-3-oxoprop-1-enyl]-2-oxo-3,4-dihydro-1,8-naphthyridin-1-yl]methyl dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
10413 afabicin
Synonyms Click here for help
AFN-1720 | Debio 1450 | Debio1450
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Afabicin dephosphono
Other databases
CAS Registry No. 1518800-35-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297501
GtoPdb PubChem SID 405560195
PubChem CID 72696796
Search Google for chemical match using the InChIKey HFYMDQMXVPJNTH-VQHVLOKHSA-N
Search Google for chemicals with the same backbone HFYMDQMXVPJNTH
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UniChem Compound Search for chemical match using the InChIKey HFYMDQMXVPJNTH-VQHVLOKHSA-N
UniChem Connectivity Search for chemical match using the InChIKey HFYMDQMXVPJNTH-VQHVLOKHSA-N