Modomics - A Database of RNA Modifications

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-threonylcarbamoyladenosine
IUPAC name2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-methylsulfanylpurin-6-yl]carbamoylamino]-3-hydroxybutanoic acid
Short namems2t6A
MODOMICS code new2000002162A
MODOMICS code2162A
Synonyms
N-[(1-Carboxy-2-hydroxypropyl)carbamoyl]-2-(methylthio)adenosine
SCHEMBL63913
Nature of the modified residueNatural
RNAMods code[
Residue unique ID55
Found in RNAYes
Related nucleotides378
Enzymes MtaB (Bacillus subtilis)
MtaB (Mus musculus)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC16H22N6O8S
Type of moietynucleoside
Degeneracynot applicable
SMILESCC(O)C(NC(Nc1nc(SC)nc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)=O)C(O)=O
logP-1.4209
TPSA237.48
Number of atoms31
Number of Hydrogen Bond Acceptors 1 (HBA1)14
Number of Hydrogen Bond Acceptors 2 (HBA2)15
Number of Hydrogen Bond Donors (HBD)7
PDB no exac match , link to the most similar ligand 12A
HMDB (Human Metabolome Database) no exact match, link to the most similar ligand None
InChIInChI=1S/C16H22N6O8S/c1-5(24)7(14(27)28)18-15(29)19-11-8-12(21-16(20-11)31-2)22(4-17-8)13-10(26)9(25)6(3-23)30-13/h4-7,9-10,13,23-26H,3H2,1-2H3,(H,27,28)(H2,18,19,20,21,29)/t5?,6-,7?,9-,10-,13-/m1/s1
InChIKeyMMNYGKPAZBIRKN-HZPYULPISA-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(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)O tautomer #0
CC(=O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #1
CC(O)C(=NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #2
CC(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)O tautomer #3
CC(=O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #4
CC(O)C(=NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #5
C=C(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #6
CC(O)=C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #7
CC(O)C(NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)O tautomer #8
CC(=O)C(NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #9
CC(O)C(=NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #10
C=C(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #11
CC(O)=C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #12
CC(O)C(NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)O tautomer #13
CC(=O)C(NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #14
CC(O)C(=NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #15
CC(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)O tautomer #16
CC(O)C(N=C(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #17
C=C(O)C(NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #18
CC(O)=C(NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #19
CC(O)C(NC(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)O tautomer #20
CC(O)C(N=C(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #21
CC(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #22
CC(=O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #23
CC(O)C(=NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #24
C=C(O)C(NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #25
CC(O)=C(NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #26
CC(O)C(NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(=O)O tautomer #27
CC(=O)C(NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #28
CC(O)C(=NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #29
CC(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #30
CC(=O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #31
CC(O)C(=NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #32
CC(O)C(NC(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)O tautomer #33
CC(O)C(N=C(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #34
C=C(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #35
CC(O)=C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #36
CC(O)C(NC(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)O tautomer #37
CC(O)C(N=C(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #38
C=C(O)C(NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #39
CC(O)=C(NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)O tautomer #40
C=C(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #41
CC(O)=C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)O tautomer #42
CC(O)C(N=C(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #43
CC(O)C(N=C(Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #44
CC(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #45
CC(O)C(NC(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)=O)=C(O)O tautomer #46
CC(O)C(N=C(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)O)C(=O)O tautomer #47
CC(O)C(NC(=Nc1nc(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #48
CC(O)C(N=C(N=c1nc(SC)[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #49
CC(O)C(N=C(N=c1[nH]c(SC)nc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #50
CC(O)C(N=C(N=C1N=C(SC)N=C2C1N=CN2C3OC(CO)C(O)C3O)O)=C(O)O tautomer #51
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ms2t6A ms2t6A ms2t6A

* 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 mass458.122
Average mass458.446
[M+H]+459.1298
Product ions327
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 groupthreonyl
heavy atomthiomethyl
othercarbamoyl

Reactions producing 2-methylthio-N6-threonylcarbamoyladenosine

Name
t6A:ms2t6A

Last modification of this entry: Sept. 22, 2023