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2D Structure
Also known as: Obi-3424, X6sh5t8h76, Th-3424, 2097713-68-1, 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide, Unii-x6sh5t8h76
Molecular Formula
C21H25N4O6P
Molecular Weight
460.4  g/mol
InChI Key
NWGZZGNICQFUHV-OAHLLOKOSA-N
FDA UNII
X6SH5T8H76

AKR1C3-activated Prodrug OBI-3424 is a small-molecule nitro-benzene, aldo-keto reductase 1C3 (AKR1C3)-activated prodrug of N,N'-bisethylenephosphoramidate, a DNA bis-alkylating agent, with potential antineoplastic activity. Upon intravenous administration, AKR1C3-activated prodrug OBI-3424 is converted to its active form by AKR1C3, which is upregulated in certain tumor cell types while not expressed in normal healthy cells. The active metabolite selectively binds to and alkylates DNA in AKR1C3-overexpressing tumor cells, resulting in DNA base pair mismatching, interstrand crosslinking and inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis. As the expression of AKR1C3 is restricted to tumors, OBI-3424 is selectively converted to its active metabolite in tumor cells only while its conversion in normal, healthy tissue is absent; this allows for an increased cytotoxic effect of the alkylating agent in tumor cells while decreasing its toxicity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[5-[(1R)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
2.1.2 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
2.1.3 InChI Key
NWGZZGNICQFUHV-OAHLLOKOSA-N
2.1.4 Canonical SMILES
CC(C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
2.1.5 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
2.2 Other Identifiers
2.2.1 UNII
X6SH5T8H76
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Obi-3424

2. X6sh5t8h76

3. Th-3424

4. 2097713-68-1

5. 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide

6. Unii-x6sh5t8h76

7. Chembl4297474

8. Schembl20870529

9. Obi3424

10. Obi-3424 [who-dd]

11. Hy-124573

12. Cs-0086947

2.4 Create Date
2017-05-06
3 Chemical and Physical Properties
Molecular Weight 460.4 g/mol
Molecular Formula C21H25N4O6P
XLogP32.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass460.15117153 g/mol
Monoisotopic Mass460.15117153 g/mol
Topological Polar Surface Area108 Ų
Heavy Atom Count32
Formal Charge0
Complexity737
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1