Modomics - A Database of RNA Modifications

i6A
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
See the molecule on the similarity map

Summary

Full nameN6-isopentenyladenosine
IUPAC name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
Short namei6A
MODOMICS code new2000000061A
MODOMICS code61A
Synonyms
2058AC
2365-40-4
2iP Riboside
2-IPA
2iPA
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(3-methylbut-2-enylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
33156-15-9
6-(3,3- paragraph signthorn(1/4)x>>uI(c)+/-u>>u degrees +/->>u)aNssE masculineEUO
6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine
6-(3,3-Dimethylallylamino)-9-(beta-D-ribofuranosyl)purine
6-(3,3-Dimethylallylamino)-9-(beta-D-ribofuranosyl)purine, 98% - 25MG 25mg
6-(3-Methyl-2-butenylamino)purine riboside
6-(.gamma.,.gamma.-Dimethylallylamino)purine riboside
6-(gamma,gamma-Dimethylallylamino)purine riboside
6-N-((3-Methyl-2-butenyl)amino)-9-beta-D-ribofuranosyl-9H-purine
6-N-((3-Methyl-2-butenyl)amino)-9-.beta.-D-ribofuranosyl-9H-purine
6-N-((3-Methyl-2-butenyl)amino)-9.beta.-D-ribofuranosylpurine
6-N-((3-Methyl-2-butenyl)amino)-9beta-D-ribofuranosylpurine
724G767
7724-76-7
8EU82FAZ5J
9.beta.-D-Ribofuranosyl-9H-purine, N-(3-methyl-2-butenylamino)-
9beta-D-Ribofuranosyl-9H-purine, N-(3-methyl-2-butenylamino)-
AC1L2NEW
ADENOSINE, N-(3-METHYL-2-BUTENYL)-
AJ-09596
AKOS016009606
Au(2) IUUO
C15-H21-N5-O4
C15H21N5O4
C16427
CAS-7724-76-7
CHEBI:62881
CHEMBL452867
CID24405
CS-W011925
D05726
DB11933
Dimethylallyladenosine
DS-5147
DSSTox_CID_31617
DSSTox_GSID_57828
DSSTox_RID_97501
DTXSID1057828
EBD80372
EINECS 231-771-3
i6a
ipa
Isopentenyl adenine riboside
Isopentenyl adenosine
Isopentenyladenosine
Isopentenyladenosine riboside
LS-15154
MFCD00005741
N-(3-Methyl-2-butenyl)adenosine
N-(3-methylbut-2-en-1-yl)adenosine
N-(3-methylbut-2-enyl)adenosine
N(6)-(2-isopentenyl)adenosine
N6-(2-Isopentenyl)adenosine
N6-(2-OiIiI(c)>>u)IUUO
N(6)-(3-methyl-2-butenyl)adenosine
N6-(3-Methyl-2-butenyl)adenosine
N6-(|A,|A- paragraph signthorn(1/4)x>>uI(c)+/-u>>u)IUUO
N6-(.DELTA.2-Isopentenyl)adenine riboside
N-6-(delta-2-Isopentenyl)adenosine
N6-(delta2-Isopentenyl)adenosine
N6-(.DELTA.2-Isopentenyl)adenosine
N(6)-(Delta(2)-isopentenyl)adenosine
N6-Dimethylallyladenosine
N6-(.gamma.,.gamma.-Dimethylallyl)adenosine
N6-Isopentenyladenine
N6-Isopentenyladenosine
N6-ISOPENTENYLADENOSINE-D6
NCGC00253650-01
N-Isopentenyladenosine
NS00037896
NSC 105546
NSC-105546
N(sup 6)-(2-Isopentenyl)adenosine
N(sup 6)-(delta(sup 2)-Isopentenyl)adenosine
N(sup 6)-Dimethylallyladenosine
N(sup 6)-Isopentenyladenosine
Q973089
Riboprin
Riboprina
Riboprina [INN-Spanish]
Riboprine
Riboprine (USAN/INN)
Riboprine [USAN:INN]
Riboprinum
Riboprinum [INN-Latin]
Ribosyl-deoxyzeatin
SB19217
SCHEMBL4599
SQ 22,558
SQ 22558
SR-01000883994
SR-01000883994-1
Tox21_113776
UNII-8EU82FAZ5J
USVMJSALORZVDV-SDBHATRESA-N
ZB001990
ZINC57125
ZIR
ZK 20 242
Nature of the modified residueNatural
RNAMods codeЧ
Residue unique ID56
Found in RNAYes
Related nucleotides253
Enzymes MiaA (Escherichia coli)
Mod5 (Saccharomyces cerevisiae)
Mod5 (Arabidopsis thaliana)
Mod5 (Homo sapiens)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC15H21N5O4
Type of moietynucleoside
Degeneracynot applicable
PubChem ID266767
ChEBI ID62881
CAS Registry Number7724-76-7
Reaxys Registry Number629507
SMILESCC(C)=CCNc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-0.1111
TPSA125.55
Number of atoms24
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
InChIInChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
InChIKeyUSVMJSALORZVDV-SDBHATRESA-N
Search the molecule in external databases ChEMBL  ChemAgora  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
8167815
14900019
29291476
47205724
47207387
49865122
57331696
57394611
78719788
103590441
104359861
126522890
129415601
135268870
135685507
162092682
163848518
163883871
170466472
175267107
179293602
223435363
223456059
223520354
226396566
241145216
250042075
252366704
252469406
255436967
255533163
275414349
275916385
297451252
300405780
310271989
312242592
315686148
316892507
316970942
319079543
321935077
321947307
329857546
340586333
341106025
341192239
341845564
342526852
347659363
347828260
348352524
349307660
355189941
355206239
363602844
373859701
374090770
375197713
375300403
375664678
376127092
378134810
381006330
381343820
381943907
383452077
385018319
385639495
386633707
387161596
403572053
404634097
404757794
404828194
405043690
405113193
406527754
419562373
434695877
438811058
439432506
441561228
442067933
442077650
442835331

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)

QM Data:

Dipole Magnitude [D]:4.595636445
Energy [Eh]:-1158.51144581621
HOMO [eV]:-8.6382
LUMO [eV]:1.0502
Gap [eV]:9.6884

Download QM Data:

Cube   .cube
Charges   charge.txt

Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
CC(C)=CCNc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #0
CC(C)=CCNc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #1
CC(C)=CCN=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O tautomer #2
CC(C)=CCN=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O tautomer #3
CC(C)=CCN=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O tautomer #4
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
i6A i6A i6A

* 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 mass335.1594
Average mass335.358
[M+H]+336.1672
Product ions204/136/148
Normalized LC elution time *3,24 (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 -
Quantitative analysis of ribonucleoside modifications in tRNA by HPLC-coupled mass spectrometry. Su D, Chan CT, Gu C, Lim KS, Chionh YH, McBee ME, Russell BS, Babu IR, Begley TJ, Dedon PC... Nat Protoc [details] 24625781 -

Chemical groups contained

TypeSubtype
otherisopentenyl

Reactions producing N6-isopentenyladenosine

Name
A:i6A

Reactions starting from N6-isopentenyladenosine

Name
i6A:io6A
i6A:ms2i6A

Last modification of this entry: Sept. 15, 2025