U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H14N4O4
Molecular Weight 230.2212
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KP-1212

SMILES

NC1=NC(=O)N(CN1)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

InChIKey=LAOLDMMWVYDDID-KVQBGUIXSA-N
InChI=1S/C8H14N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h4-6,13-14H,1-3H2,(H3,9,10,11,15)/t4-,5+,6+/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H14N4O4
Molecular Weight 230.2212
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 11:32:49 GMT 2023
Edited
by admin
on Sat Dec 16 11:32:49 GMT 2023
Record UNII
ZV3RS7MHH7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KP-1212
Code English
1,3,5-TRIAZIN-2(1H)-ONE, 4-AMINO-1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-3,6-DIHYDRO-
Systematic Name English
SN-1212
Code English
6-AMINO-3-((2R,4S,5R)-4-HYDROXY-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2-YL)-1,2-DIHYDRO-1,3,5-TRIAZIN-4-ONE
Systematic Name English
KP1212
Code English
4-AMINO-1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-3,6-DIHYDRO-1,3,5-TRIAZIN-2(1H)-ONE
Systematic Name English
DHDAC
Common Name English
2'-DEOXY-5,6-DIHYDRO-5-AZACYTIDINE
Common Name English
Code System Code Type Description
CAS
114522-16-6
Created by admin on Sat Dec 16 11:32:49 GMT 2023 , Edited by admin on Sat Dec 16 11:32:49 GMT 2023
PRIMARY
PUBCHEM
9859433
Created by admin on Sat Dec 16 11:32:49 GMT 2023 , Edited by admin on Sat Dec 16 11:32:49 GMT 2023
PRIMARY
FDA UNII
ZV3RS7MHH7
Created by admin on Sat Dec 16 11:32:49 GMT 2023 , Edited by admin on Sat Dec 16 11:32:49 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
This nucleoside (KP-1212) is not a chain terminator but exerts its antiviral effects via mutagenesis of the viral genome. Serial passaging of HIV in the presence of KP-1212 causes an increase in the mutation rate of the virus leading to viral ablation. HIV strains resistant to KP-1212 have not yet been isolated. Quite to the contrary, virus treated with KP-1212 exhibited an increased sensitivity not only to KP-1212 but also to another nucleoside reverse transcriptase inhibitor (NRTI), zidovudine.
ACTIVE MOIETY
Specifically, KP1212 is a mutagenic deoxycytidine analog that elevates the G to A mutations in viral genome shown by clinical studies. It was hypothesized that the mutation originates from the tautomerization of KP1212 from the canonical amino-keto form to the imino-keto form, which results in favorable base pairing to A.