Summary

Full nameinosine
IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
Short nameI
MODOMICS code9A
Synonyms
1,9-dihydro-9-b-D-ribofuranosyl-6H-Purin-6-one
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one
1a4m
2ada
2fqw
(2R,3R,4S,5R)-2-(6-Hydroxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol
3h-inosine
58-63-9
5A614L51CT
6H-Purin-6-one, 1,9-dihydro-9-beta-D-ribofuranosyl-
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purin-6-one
9-[(2S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
9-(3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1,9-DIHYDRO-PURIN-6-ONE
9-b-D-ribofuranosyl-Hypoxanthine
9-b-D-Ribofuranosylhypoxanthine
9-beta-delta-ribofuranosyl-Hypoxanthine
9-beta-delta-Ribofuranosylhypoxanthine
9beta-delta-Ribofuranosylhypoxanthine
9-beta-D-Ribofuranosyl-1,9-dihydro-6H-purin-6-one (Inosine)
9-beta-D-ribofuranosyl-9H-purin-6-ol
9-(beta-D-ribofuranosyl)-9H-purin-6-ol
9-beta-D-ribofuranosyl-Hypoxanthine
9-beta-D-Ribofuranosylhypoxanthine
9.beta.-D-Ribofuranosylhypoxanthine
9-.beta.-D-Ribofuranosylhypoxanthine
9beta-D-Ribofuranosylhypoxanthine
A-8687
AB0066076
AB1000320
AC1L1LMO
AC1Q77T9
AC89F8E4-FD89-45EE-8B41-94DFC07AB42F
AI3-52241
AKOS015969695
AKOS015995607
AKOS024462561
AM83935
AMY30713
AN-889
ANW-33000
ARONIS24558
AS-11754
Atorel
Atorel; HXR; Hypoxanthine D-riboside
B3677
BDBM22104
BDBM50366815
beta-delta-Ribofuranoside hypoxanthine-9
.beta.-D-Ribofuranoside, hypoxanthine-9
beta-D-Ribofuranoside hypoxanthine-9
beta-D-Ribofuranoside, hypoxanthine-9
.beta.-Inosine
beta-Inosine
bmse000098
bmse000888
bmse000978
BRD-K79612754-001-21-7
C00294
C10-H12-N4-O5
C10H12N4O5
CAS-58-63-9
Catacol
CCG-267127
CHEBI:17596
CHEMBL1556
CID 5274258
cid_6021
CID6021
CJ-13587
cMAP_000084
CS-5845
CTK1G9965
D00054
D007288
DB-029916
DB04335
D-Inosine
DSSTox_CID_25993
DSSTox_GSID_45993
DSSTox_RID_81278
DTXSID2045993
EINECS 200-390-4
ERK5-6N10
GTPL4554
HMS2235I17
HXR
HY-N0092
Hypoxanthine 9-|A-D-ribofuranoside
Hypoxanthine 9-beta-delta-ribofuranoside
Hypoxanthine 9-beta-D-ribofuranoside
Hypoxanthine, 9-beta-D-ribofuranosyl-
Hypoxanthine, 9-.beta.-D-ribofuranosyl-
Hypoxanthine arabinoside
Hypoxanthine D-riboside
Hypoxanthine nucleoside
Hypoxanthine ribonucleoside
Hypoxanthine riboside
hypoxanthine-9 beta-delta-Ribofuranoside
hypoxanthine-9 beta-D-Ribofuranoside
Hypoxanthine-9-beta-delta-ribofuranoside
Hypoxanthine-9-beta-D-ribofuranoside
Hypoxanthine-9-delta-ribofuranoside
Hypoxanthine-9-D-ribofuranoside
hypoxanthine-ribose
Hypoxanthosine
I0037
InChI=1/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s
INDOLE-3-CARBOXALDEHYDE
INO
INO 495
INO-1001
Inosie
inosin-
Inosin
Inosina
Inosina [INN-Spanish]
inosine
(-)-Inosine
Inosine-
Inosine (8CI,9CI)
Inosine, 99%
Inosine, 99% - 100G 100g
Inosine 99% for biochemistry 5gm
Inosine, >=99% (HPLC)
Inosine [INN:JAN]
Inosine (JAN/INN)
Inosine (<lt/> 100 microg/ml) in methanol
Inosine,(S)
Inosinum
Inosinum [INN-Latin]
Inotin (TN)
iso-prinosine
J10406
KBio2_002560
KBio2_005128
KBio2_007696
KBio3_003038
KBioGR_002560
KBioSS_002569
KSC269S6L
LS-84000
MCULE-3095132846
MFCD00066770
MLS000028518
NCGC00095787-01
NCGC00095787-05
NCGC00096119-02
NCGC00096119-03
NOS
NS00010210
NSC 20262
NSC-20262
NSC20262
Opera_ID_1628
Oxiamin
Panholic-L
Pantholic-L
PubChem14189
Q422564
Ribonosine
riboxine
RTR-037177
s2442
SCHEMBL15804
Selfer
SMP1_000165
SMR000058316
SR-01000721862
SR-01000721862-2
SR-01000721862-3
Tox21_111522
Tox21_111522_1
TR-037177
Trophicardyl
UGQMRVRMYYASKQ-KQYNXXCUSA-N
UNII-5A614L51CT
ZINC8855117

Nature of the modified residueNatural
RNAMods codeI
Residue unique ID113
Found in RNAYes
Related nucleotides217
Enzymes Tad1 (Saccharomyces cerevisiae)
Tad1 (Homo sapiens)
Tad2 (Saccharomyces cerevisiae)
Tad3 (Saccharomyces cerevisiae)
TadA (Escherichia coli)
TadA (Arabidopsis thaliana)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC10H12N4O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID6021
SMILESOC[C@@H]1[C@@H](O)[C@@H](O)[C@H]([n]2c3nc[nH]c(=O)c3nc2)O1
logP-2.2689
TPSA133.49
Number of atoms19
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)8
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand NOS
PDB exact match , link to the most similar ligand NOS
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000195
InChIInChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChIKeyUGQMRVRMYYASKQ-KQYNXXCUSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
2827
3588
603219
831627
841594
855079
3133546
7847122
7889457
8012950
8027801
8139984
8144594
10318627
10528369
11364968
11367530
11370092
11373131
11375692
11378263
14774889
14799194
14947343
15197267
16072360
22390403
24896051
26702299
29204274
29225035
46391392
46393791
46394141
47794633
48259418
49661631
49845920
49985030
57323122
80900400
85164937
85747831
87326006
87571444
87895528
88782647
92298201
92469745
104310893
117613648
123094743
124801235
126497004
126497007
127898273
129365654
131269405
134224896
134228455
134419359
134419365
134971803
135724906
136067793
137756472
142878044
143491612
144080979
144205075
152109114
152135026
152242386
160649913
160800501
160843981
160845917
162096388
162102976
162173203
162547171
163805494
163884603
166223214
170465655
172088299
175426857
178101275
179150391
179236110
186017463
198971754
202549456
204370950
204940360
223399183
223498941
223674793
223749297
226406087
241381394
250014984
250225220
252400669
252401768
252403307
254761333
255470538
258709505
273066889
274953597
275952058
277309445
297479652
300404234
310275244
312225660
312695156
313081167
315681612
316396486
316604596
316935171
318154709
318162915
318474039
318478038
319064020
319489152
319554079
321934529
321946662
333473487
336179682
340080835
340509514
340520033
341141025
341164145
341274377
341326364
342526854
342583821
346693598
347759127
347913638
348274309
349141148
350089685
354266180
354302981
355036838
363603042
363676579
366185987
371630121
374037466
375135025
375162909
375293292
375683031
376034294
376125360
376166383
376166384
376166385
376166386
376197833
376386860
376659274
381001594
381011670
381118607
381338258
381364953
381623061
383231705
383516332
384252527
384653586
385219140
385219153
385784961
386621875
387061456
387159226
403379854
404332229
404738483
404769253
404827255
405133431
405559132
406183998
406729582
425208283
433775077
433776083
433776367
433776729
433776964
433777422
433777423
433777975
433837503
434132662
434296574
434697691
438458960
438515036
440065760
441074115
441119467
441238804
441296926
441556219
441579651
442115219
443508591
443548643

* 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
OCC1C(O)C(O)C(n2c3ncnc(O)c3nc2)O1 tautomer #0
OCC1C(O)C(O)C(n2c3[nH]cnc(=O)c3nc2)O1 tautomer #1
OCC1C(O)C(O)C(n2c3nc[nH]c(=O)c3nc2)O1 tautomer #2
OCC1C(O)C(O)C(n2c3ncnc(O)c3nc2)O1 tautomer #3
OCC1C(O)C(O)C(N2C3=NC=NC(=O)C3N=C2)O1 tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
I I I

* 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 mass268.0808
Average mass268.226
[M+H]+269.0886
Product ions137
Normalized LC elution time *0,95 (Kellner 2014, Kellner 2014)
LC elution order/characteristicsbetween U and G (Kellner 2014, 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 -
Absolute and relative quantification of RNA modifications via biosynthetic isotopomers. Kellner S, Ochel A, Thuring K, Spenkuch F, Neumann J, Sharma S, Entian KD, Schneider D, Helm M... Nucleic Acids Res [details] 25129236 -

Chemical groups contained

TypeSubtype
otherketo

Reactions producing inosine

Name
A:I

Reactions starting from inosine

Name
I:m1I
I:Im

Last modification of this entry: Sept. 29, 2021


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