Summary

Full nameN6,2'-O-dimethyladenosine
IUPAC name(2R,3R,4R,5R)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol
Short namem6Am
MODOMICS code06A
Synonyms
(2R,3R,4R,5R)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol
3-Glucosaminoglycan sulfate
3GS
57817-83-1
57821-29-1
AC1O57LU
Adenosine, N-methyl-2'-O-methyl-
Aterina
C007858
C12-H17-N5-O4
CID6453528
DTXSID50206530
Glucuronyl glucosamine glycan sulfate
Glucuronyl glucosaminoglycan sulfate
Glucuronylglucosamine-glicane sulfate
Glucuronylglucosamineglicane sulfate
glucuronylglucosaminoglycan sulfate
Gluparin
KRX-101
LEV25J2GTV
Luzone
N,2'-O-Dimethyladenosine
n6,2'-O-dimethyladenosine
n6-methyl-2'-o-methyladenosine
N6,O2'-Dimethyladenosine
N(6),O(2)-Dimethyladenosine
Provenal
SCHEMBL665209
Sulodexide
Sulodexide [INN]
Sulodexido
Sulodexido [INN-Spanish]
Sulodexidum
Sulodexidum [INN-Latin]
Treparin
UNII-75HGV0062C
UNII-LEV25J2GTV
Vessel
Vessel 2F
Vessel Due F
ZLA0007
zlchem 6

Nature of the modified residueNatural
RNAMods codeχ
Residue unique ID82
Found in RNAYes
Related nucleotides430
Found naturally in RNA typessnRNA

Chemical information

Sum formulaC12H17N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2cnc3c2ncnc3NC)O[C@H](CO)[C@H]1O
logP-0.7934
TPSA114.55
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand 26A
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004044
InChIInChI=1S/C12H17N5O4/c1-13-10-7-11(15-4-14-10)17(5-16-7)12-9(20-2)8(19)6(3-18)21-12/h4-6,8-9,12,18-19H,3H2,1-2H3,(H,13,14,15)/t6-,8-,9-,12-/m1/s1
InChIKeyGRYSXUXXBDSYRT-WOUKDFQISA-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
COC1C(n2cnc3c2ncnc3NC)OC(CO)C1O tautomer #0
COC1C(n2cnc3c2ncnc3NC)OC(CO)C1O tautomer #1
COC1C(n2cnc3c2[nH]cnc3=NC)OC(CO)C1O tautomer #2
COC1C(n2cnc3c2nc[nH]c3=NC)OC(CO)C1O tautomer #3
COC1C(N2C=NC3C2=NC=NC3=NC)OC(CO)C1O tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m6Am m6Am m6Am

* 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 mass295.1281
Average mass295.294
[M+H]+296.1359
Product ions150
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 O2
methyl groupmethyl at other N

Reactions producing N6,2'-O-dimethyladenosine

Name
m6A:m6Am
Am:m6Am

Reactions starting from N6,2'-O-dimethyladenosine

Name
m6Am:m6,6Am

Last modification of this entry: Sept. 29, 2021


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