Summary

Full nameN6-methyl-N6-threonylcarbamoyladenosine
IUPAC name(2S,3R)-2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]carbamoylamino]-3-hydroxybutanoic acid
Short namem6t6A
MODOMICS code662A
Synonyms
24719-82-2
28874-45-5
28882-41-9
(2S,3R)-2-(3-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)ureido)-3-hydroxybutanoic acid
(2S,3R)-2-[({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}carbamoyl)amino]-3-hydroxybutanoic acid
(2S,3R)-2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]carbamoylamino]-3-hydroxybutanoic acid
(2s,3r)-2-[({9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9h-purin-6-yl}carbamoyl)amino]-3-hydroxybutanoic acid(non-preferred name)
3C55P4W4TB
((9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamoyl)-L-threonine
AC1L4PHC
AC1Q5QSL
Acaptma
AR-1A3389
AR-1A3390
C15-H26-N3-O.Br.Br-H
C15H26N3O.Br.BrH
CHEBI:21440
CID161466
DTXSID70947655
KST-1A3490
KST-1A3491
L-Threonine, N-(((9-beta-D-ribofuranosyl-9H-purin-6-yl)amino)carbonyl)-
N-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}adenosine
N6-[((1S,2R)-1-CARBOXY-2-HYDROXYBUTYLAMINO)CARBONYL]ADENOSINE SODIUM SALT
N6-Carbamoyl-L-threonyladenosine
N6-Carbamoylthreonyladenosine
n6-(n-threonylcarbonyl)adenosine
N(6)-(N-Threonylcarbonyl)adenosine
N6-Threoninocarbonyladenosine
N6-Threonylcarbamoyladenosine
N-[(9- -D-ribofuranosylpurin-6-yl)carbamoyl]threonine
N-[(9-beta-D-ribofuranosylpurin-6-yl)carbamoyl]-L-threonine
N-[(9-beta-D-ribofuranosylpurin-6-yl)carbamoyl]threonine
N-((9-beta-D-Ribofuranosylpurin-6-yl)-carbamoyl)threonine
N(epsilon-Aminocaproyl)-p-aminophenyltrimethylammonium
N-{Hydroxy[(9-pentofuranosyl-9H-purin-6-yl)amino]methylidene}threonine
N-(Purin-6-ylcarbamoyl)-L-threonine riboside
Q15632802
SCHEMBL63155
t(6)a
T6a
UNII-3C55P4W4TB
ZINC31474771

Nature of the modified residueNatural
RNAMods codeE
Residue unique ID16
Found in RNAYes
Related nucleotides231
Enzymes TRMO (Homo sapiens)
TrmO (Escherichia coli)
Found in phylogenyEubacteria
Found naturally in RNA typestRNA

Chemical information

Sum formulaC15H20N6O8
Type of moietynucleoside
Degeneracynot applicable
SMILESC[C@H]([C@@H](C(=O)O)NC(Nc1c2c([n]([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)cn2)ncn1)=O)O
logP-2.1428
TPSA212.18
Number of atoms29
Number of Hydrogen Bond Acceptors 1 (HBA1)13
Number of Hydrogen Bond Acceptors 2 (HBA2)14
Number of Hydrogen Bond Donors (HBD)7
PDB no exac match , link to the most similar ligand AET
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0041623
InChIInChI=1S/C15H20N6O8/c1-5(23)7(14(26)27)19-15(28)20-11-8-12(17-3-16-11)21(4-18-8)13-10(25)9(24)6(2-22)29-13/h3-7,9-10,13,22-25H,2H2,1H3,(H,26,27)(H2,16,17,19,20,28)/t5-,6-,7+,9-,10-,13-/m1/s1
InChIKeyUNUYMBPXEFMLNW-DWVDDHQFSA-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(C(O)=O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #0
CC(C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)=O tautomer #1
CC(C(C(O)O)=NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #2
CC(C(C(O)=O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #3
CC(C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)=O tautomer #4
CC(C(C(O)O)=NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #5
C=C(C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #6
C=C(C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #7
CC(=C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #8
CC(=C(C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #9
CC(C(C(O)=O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)O tautomer #10
CC(C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)=O tautomer #11
CC(C(C(O)O)=NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)O tautomer #12
CC(C(C(O)=O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)O tautomer #13
CC(C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)=O tautomer #14
CC(C(C(O)O)=NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)O tautomer #15
CC(C(=C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #16
CC(C(=C(O)O)NC(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)=O)O tautomer #17
CC(C(C(O)=O)N=C(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #18
CC(C(C(O)=O)N=C(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #19
CC(C(C(O)=O)NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #20
CC(C(C(O)O)NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)=O tautomer #21
CC(C(C(O)O)=NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #22
C=C(C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)O tautomer #23
C=C(C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)O tautomer #24
CC(C(C(O)=O)NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)O tautomer #25
CC(C(C(O)O)NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)=O tautomer #26
CC(C(C(O)O)=NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)O tautomer #27
CC(=C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)O tautomer #28
CC(=C(C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)O tautomer #29
C=C(C(C(O)O)NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #30
CC(=C(C(O)O)NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #31
C=C(C(C(O)O)NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)O tautomer #32
CC(C(=C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)=O)O tautomer #33
CC(C(=C(O)O)NC(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)=O)O tautomer #34
CC(C(C(O)=O)N=C(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)O)O tautomer #35
CC(C(C(O)=O)N=C(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)O)O tautomer #36
CC(=C(C(O)O)NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)O tautomer #37
CC(C(=C(O)O)N=C(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #38
CC(C(=C(O)O)N=C(Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #39
CC(C(=C(O)O)NC(=Nc1c2c(n(C3C(O)C(O)C(CO)O3)cn2)ncn1)O)O tautomer #40
CC(C(=C(O)O)NC(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)=O)O tautomer #41
CC(C(C(O)=O)N=C(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)O)O tautomer #42
CC(C(=C(O)O)N=C(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)[nH]cn1)O)O tautomer #43
CC(C(=C(O)O)N=C(N=c1c2c(n(C3C(O)C(O)C(CO)O3)cn2)nc[nH]1)O)O tautomer #44
CC(C(=C(O)O)N=C(N=C1C2C(N(C3C(O)C(O)C(CO)O3)C=N2)=NC=N1)O)O tautomer #45

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m6t6A m6t6A m6t6A

* 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 mass426.1499
Average mass412.355
[M+H]+427.1577
Product ions295
Normalized LC elution time *1,93 (Kellner 2014)
LC elution order/characteristicsbetween A and 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
aminoacyl groupthreonyl
methyl groupmethyl at other N
othercarbamoyl

Reactions producing N6-methyl-N6-threonylcarbamoyladenosine

Name
t6A:m6t6A

Last modification of this entry: Sept. 29, 2021


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