OBI-3424   Click here for help

GtoPdb Ligand ID: 12770

Synonyms: OBI3424 | TH-3424 | TH3424
PDB Ligand
Compound class: Synthetic organic
Comment: OBI-3424 is a prodrug that is converted (activated) by aldo-keto reductase family 1 member C3 (AKR1C3) into an intermediary metabolite that spontaneously hydrolyses to generate a thiotepa-related DNA alkylating (cross-linking) agent [1]. It was designed as a chemotherapeutic agent, and has demonstrated efficacy in preclinical models of T-cell acute lymphoblastic leukemia (T-ALL).
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.

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Canonical SMILES C[C@H](C1=CC=C(C(=C1)OC2=CC(=CC=C2)C(=O)N(C)C)[N+](=O)[O-])OP(=O)(N3CC3)N4CC4
Isomeric SMILES C[C@H](C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
InChI InChI=1S/C21H25N4O6P/c1-15(31-32(29,23-9-10-23)24-11-12-24)16-7-8-19(25(27)28)20(14-16)30-18-6-4-5-17(13-18)21(26)22(2)3/h4-8,13-15H,9-12H2,1-3H3/t15-/m1/s1
InChI Key NWGZZGNICQFUHV-OAHLLOKOSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-[5-[(1R)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
Synonyms Click here for help
OBI3424 | TH-3424 | TH3424
Database Links Click here for help
CAS Registry No. 2097713-68-1 (source: PubChem)
ChEMBL Ligand CHEMBL4297474
GtoPdb PubChem SID 483123318
PubChem CID 126961329
RCSB PDB Ligand 6LG
Search Google for chemical match using the InChIKey NWGZZGNICQFUHV-OAHLLOKOSA-N
Search Google for chemicals with the same backbone NWGZZGNICQFUHV
UniChem Compound Search for chemical match using the InChIKey NWGZZGNICQFUHV-OAHLLOKOSA-N
UniChem Connectivity Search for chemical match using the InChIKey NWGZZGNICQFUHV-OAHLLOKOSA-N