Summary

Full nameperoxywybutosine
IUPAC namemethyl 4-[3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6-dimethyl-9-oxoimidazo[1,2-a]purin-7-yl]-3-hydroperoxy-2-(methoxycarbonylamino)butanoate
Short nameo2yW
MODOMICS code34832G
Synonyms
2-(Methoxycarbonylamino)-3-hydroperoxy-4-[3-(beta-D-ribofuranosyl)-4,6-dimethyl-9-oxo-4,9-dihydro-3H-imidazo[1,2-a]purine-7-yl]butyric acid methyl ester
3H-Imidazo(1,2-a)purine-7-butanoic acid, 4,9-dihydro-beta-hydroperoxy-alpha-((methoxycarbonyl)amino)-4,6-dimethyl-9-oxo-3-beta-D-ribofuranosyl-, methyl ester
7-(2-Hydroperoxy-3-{[hydroxy(methoxy)methylidene]amino}-4-methoxy-4-oxobutyl)-4,6-dimethyl-3-pentofuranosyl-3,4-dihydro-9H-imidazo[1,2-a]purin-9-one
78355-49-4
AC1L4TTN
CID192142
DTXSID50999697
methyl 4-[3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6-dimethyl-9-oxoimidazo[1,2-a]purin-7-yl]-3-hydroperoxy-2-(methoxycarbonylamino)butanoate
Peroxy Y nucleoside

Nature of the modified residueNatural
RNAMods codeW
Residue unique ID121
Found in RNAYes
Related nucleotides422
Found naturally in RNA typestRNA

Chemical information

Sum formulaC21H28N6O11
Type of moietynucleoside
Degeneracynot applicable
SMILESC[n]1c2c(nc[n]2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[n]2c1nc(C)c2CC(OO)C(NC(OC)=O)C(OC)=O
logP-2.0082
TPSA221.13
Number of atoms38
Number of Hydrogen Bond Acceptors 1 (HBA1)14
Number of Hydrogen Bond Acceptors 2 (HBA2)17
Number of Hydrogen Bond Donors (HBD)5
PDB no exac match , link to the most similar ligand YG
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0039126
InChIInChI=1S/C21H28N6O11/c1-8-9(5-10(38-34)12(19(32)35-3)24-21(33)36-4)27-17(31)13-16(25(2)20(27)23-8)26(7-22-13)18-15(30)14(29)11(6-28)37-18/h7,10-12,14-15,18,28-30,34H,5-6H2,1-4H3,(H,24,33)/t10?,11-,12?,14-,15-,18-/m1/s1
InChIKeyWCNMEQDMUYVWMJ-HSRLSWODSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)C(=NC(OC)=O)C(OC)O tautomer #0
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)C(NC(OC)=O)C(OC)=O tautomer #1
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)=C(NC(OC)=O)C(OC)O tautomer #2
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)C(NC(OC)=O)=C(OC)O tautomer #3
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)C(N=C(OC)O)C(OC)=O tautomer #4
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(OO)C(N=C(OC)O)=C(OC)O tautomer #5

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
o2yW o2yW o2yW

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic mass540.1816
Average mass540.481
[M+H]+541.1894
Product ions409
Normalized LC elution time * not available
LC elution order/characteristics not available

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.

Comments

Putative.

Chemical groups contained

TypeSubtype
aminoacyl groupglutamyl
otheracetylamide
othermethylester
otherperoxy
ring modificationwyosine

Reactions producing peroxywybutosine

Name
OHyW:o2yW

Last modification of this entry: Sept. 29, 2021


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