Summary

Full namehydroxywybutosine
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-hydroxy-2-(methoxycarbonylamino)butanoate
Short nameOHyW
MODOMICS code34830G
Synonyms
2-(Methoxycarbonylamino)-3-hydroxy-4-(3-beta-D-ribofuranosyl-4,6-dimethyl-9-oxo-3,4-dihydro-9H-imidazo[1,2-a]purine-7-yl)butanoic acid methyl ester

Nature of the modified residueNatural
RNAMods code
Residue unique ID97
Found in RNAYes
Related nucleotides418

Chemical information

Sum formulaC21H28N6O10
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(O)C(NC(OC)=O)C(OC)=O
logP-2.5055
TPSA211.9
Number of atoms37
Number of Hydrogen Bond Acceptors 1 (HBA1)13
Number of Hydrogen Bond Acceptors 2 (HBA2)16
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/C21H28N6O10/c1-8-9(5-10(29)12(19(33)35-3)24-21(34)36-4)27-17(32)13-16(25(2)20(27)23-8)26(7-22-13)18-15(31)14(30)11(6-28)37-18/h7,10-12,14-15,18,28-31H,5-6H2,1-4H3,(H,24,34)/t10?,11-,12?,14-,15-,18-/m1/s1
InChIKeyOBCAXUIWCCSJPT-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(=O)C(NC(OC)=O)C(OC)O tautomer #0
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)C(=NC(OC)=O)C(OC)O tautomer #1
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)C(NC(OC)=O)C(OC)=O tautomer #2
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4C=C(O)C(NC(OC)=O)C(OC)O tautomer #3
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)C(NC(OC)=O)=C(OC)O tautomer #4
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)=C(NC(OC)=O)C(OC)O tautomer #5
CN1c2c(ncn2C3OC(CO)C(O)C3O)C(=O)N4C1=NC(C)C4=CC(=O)C(NC(OC)=O)C(OC)O tautomer #6
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)C(N=C(OC)O)C(OC)=O tautomer #7
Cn1c2c(ncn2C3OC(CO)C(O)C3O)c(=O)n4c1nc(C)c4CC(O)C(N=C(OC)O)=C(OC)O tautomer #8

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
OHyW OHyW OHyW

* 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 mass524.1867
Average mass524.481
[M+H]+525.1945
Product ions393
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.

Chemical groups contained

TypeSubtype
aminoacyl groupglutamyl
otheracetylamide
otherhydroxyl
othermethylester
ring modificationwyosine

Reactions producing hydroxywybutosine

Name
OHyWy:OHyW

Reactions starting from hydroxywybutosine

Name
OHyW:o2yW

Last modification of this entry: Sept. 29, 2021


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