Summary

Full nameisowyosine
IUPAC name3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7-dimethyl-5H-imidazo[1,2-a]purin-9-one
Short nameimG2
MODOMICS code42G
Synonyms
3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7-dimethyl-5H-imidazo[1,2-a]purin-9-one
imG2
isowyosine

Nature of the modified residueNatural
RNAMods code
Residue unique ID89
Found in RNAYes
Related nucleotides419
Enzymes Taw22 (Pyrococcus abyssi)

Chemical information

Sum formulaC14H17N5O5
Type of moietynucleoside
Degeneracynot applicable
SMILESCc1nc2[nH]c3c(c(=O)[n]2c1C)nc[n]3[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-1.3994
TPSA137.9
Number of atoms24
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand NOS
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000195
InChIInChI=1S/C14H17N5O5/c1-5-6(2)19-12(23)8-11(17-14(19)16-5)18(4-15-8)13-10(22)9(21)7(3-20)24-13/h4,7,9-10,13,20-22H,3H2,1-2H3,(H,16,17)/t7-,9-,10-,13-/m1/s1
InChIKeyBINGDNLMMYSZFR-QYVSTXNMSA-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
Cc1nc2[nH]c3c(c(=O)n2c1C)ncn3C4OC(CO)C(O)C4O tautomer #0
Cc1nc2nc3c(c(O)n2c1C)ncn3C4OC(CO)C(O)C4O tautomer #1
CC1=Nc2nc3c(c(=O)n2C1C)ncn3C4OC(CO)C(O)C4O tautomer #2
Cc1[nH]c2nc3c(c(=O)n2c1C)ncn3C4OC(CO)C(O)C4O tautomer #3
C=C1Nc2nc3c(c(=O)n2C1C)ncn3C4OC(CO)C(O)C4O tautomer #4
Cc1nc2N=C3C(C(=O)n2c1C)N=CN3C4OC(CO)C(O)C4O tautomer #5

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
imG2 imG2 imG2

* 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 mass335.123
Average mass335.315
[M+H]+336.1308
Product ions204
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
methyl groupmethyl at aromatic C
ring modificationwyosine

Reactions producing isowyosine

Name
imG-14:imG2

Reactions starting from isowyosine

Name
imG2:mimG

Last modification of this entry: Sept. 29, 2021


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