Modomics - A Database of RNA Modifications

ms2i6A
The molecule is shown in a ball-and-stick representation with the following colors for atoms :
⬤ Hydrogen (H): white ⬤ Carbon (C): gray ⬤ Oxygen (O): red ⬤ Phosphorus (P): orange ⬤ Nitrogen (N): blue ⬤ Selenium (Se): gold ⬤ Sulfur (S): yellow

Summary

Full name2-methylthio-N6-isopentenyladenosine
IUPAC name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)-2-methylsulfanylpurin-9-yl]oxolane-3,4-diol
Short namems2i6A
MODOMICS code new2000002161A
MODOMICS code2161A
Synonyms
20859-00-1
23743-97-7
2374-61-0
2-Methylthio-N6-(.delta.2-isopentenyl)adenosine
2-Methylthio-N6-(delta2-isopentenyl)adenosine
2-methylthio-N(6)-(Delta(2)-isopentenyl)adenosine
2-methylthio-n6-dimethylallyladenosine
2-Methylthio-N6-(.gamma.,.gamma.-dimethylallyl)adenosine
2-Methylthio-N-6-isopentenyladenosine
2-Methylthio-N6-isopentenyladenosine
2-Methylthio-N(6)-isopentenyladenosine
2-Methyl-thio-N-6-isopentyladenosine
2MSA
2-Mtia
(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-((3-methylbut-2-en-1-yl)amino)-2-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)-2-methylsulfanylpurin-9-yl]oxolane-3,4-diol
AC1L4P8M
AC1Q4XZ5
Adenosine, N-(3-methyl-2-butenyl)-2-(methylthio)-
AR-1H6608
AR-1H6609
CHEBI:62875
CID161337
DTXSID30943113
ms2i6A
N-(3-Methyl-2-butenyl)-2-(methylthio)adenosine
N-(3-Methylbut-2-en-1-yl)-2-(methylsulfanyl)-9-pentofuranosyl-9H-purin-6-amine
N-(3-methylbut-2-en-1-yl)-2-(methylsulfanyl)adenosine
N6-(.delta.2-Isopentenyl)-2-methylthioadenosine
N(6)-(delta(2)-Isopentenyl)-2-methylthioadenosine
N6-Isopentenyl-2-thiomethyladenosine
Q27132248
Ribosyl-2-methylthio-cis-zeatin
SCHEMBL18171845
VZQXUWKZDSEQRR-SDBHATRESA-N
Nature of the modified residueNatural
RNAMods code*
Residue unique ID51
Found in RNAYes
Related nucleotides240
Enzymes MiaB (Escherichia coli)
MiaB (Bacillus subtilis)
MiaB (Thermotoga maritima)
Found in phylogenyEubacteria
Found naturally in RNA typestRNA

Chemical information

Sum formulaC16H23N5O4S
Type of moietynucleoside
Degeneracynot applicable
PubChem ID161337
SMILESCC(C)=CCNc1nc(SC)nc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP0.6108
TPSA150.85
Number of atoms26
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)10
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand ZIR
HMDB (Human Metabolome Database) no exact match, link to the most similar ligand None
InChIInChI=1S/C16H23N5O4S/c1-8(2)4-5-17-13-10-14(20-16(19-13)26-3)21(7-18-10)15-12(24)11(23)9(6-22)25-15/h4,7,9,11-12,15,22-24H,5-6H2,1-3H3,(H,17,19,20)/t9-,11-,12-,15-/m1/s1
InChIKeyVZQXUWKZDSEQRR-SDBHATRESA-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
CC(C)=CCNc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O tautomer #0
CC(C)=CCNc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O tautomer #1
CC(C)=CCN=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O tautomer #2
CC(C)=CCN=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O tautomer #3
CC(C)=CCN=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O tautomer #4
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ms2i6A ms2i6A ms2i6A

* 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 mass381.1471
Average mass381.45
[M+H]+382.1549
Product ions250
Normalized LC elution time *3,54 (Kellner 2014)
LC elution order/characteristicsafter m6A (Kellner 2014)

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


LC-MS Publications

Title Authors Journal Details PubMed Id DOI
Profiling of RNA modifications by multiplexed stable isotope labelling. Kellner S, Neumann J, Rosenkranz D, Lebedeva S, Ketting RF, Zischler H, Schneider D, Helm M. Chem Commun (Camb). [details] 24567952 -

Chemical groups contained

TypeSubtype
heavy atomthiomethyl
otherisopentenyl

Reactions producing 2-methylthio-N6-isopentenyladenosine

Name
i6A:ms2i6A

Reactions starting from 2-methylthio-N6-isopentenyladenosine

Name
ms2i6A:ms2io6A

Last modification of this entry: Sept. 22, 2023