Summary

Full nameadenosine
IUPAC name(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Short nameA
MODOMICS codeA
Nature of the modified residueNatural
RNAMods codeA
Residue unique ID109
Found in RNAYes
Related nucleotides444
Enzymes ALKBH5 (Homo sapiens)
FTO (Homo sapiens)
Found in phylogenyArchaea, Eubacteria, Eukaryota

Chemical information

Sum formulaC10H13N5O4
Type of moietynucleoside
Degeneracynot applicable
PubChem ID60961
SMILESNc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-1.3988
TPSA139.54
Number of atoms19
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand ADN
PDB exact match , link to the most similar ligand ADN
HMDB (Human Metabolome Database) exact match HMDB0000050
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000050
InChIInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
2103
3512
584484
584490
585862
586357
597013
819854
821994
823447
825728
826920
828107
828519
829493
830178
830391
833174
833907
836875
837192
855078
855932
3136392
7847113
7885717
7978645
8023217
8024149
8027268
8143428
8187141
10318629
11110168
11120317
11120805
11121293
11371396
11484930
11489073
11490104
11532406
11532673
11537606
14716094
14774851
14799162
22394812
24277685
24698217
24875177
24890739
26611593
26679885
26703421
26718521
26746554
26751564
29196283
29196284
30894316
43118274
46392770
46394143
46394193
46394457
46484664
46508728
47170007
47885198
48415518
49655269
49655272
49833639
49865053
50104175
50104176
50104177
53776935
53789432
56436529
56462979
56479554
57314201
57410855
76747733
81044335
81044589
81060289
81061992
81067306
81067308
85164908
85747823
85856093
87235637
87235640
87235942
87561839
88881212
89449259
90341699
92092948
92123937
92297858
92307323
92708890
93578298
99205913
99206458
99213397
99213399
99344330
103059163
103168984
104234127
104322053
113585170
117358470
117529572
121360335
124511102
124636671
124801154
124807074
124807076
125011540
125317120
126531873
126610610
126617407
126648007
127710303
128808466
128814610
131349748
134419356
134419362
134465061
134465064
135017562
135023145
135363564
135651426
135697784
136905477
141402135
144074868
144087463
144187457
144204442
144220196
144223831
152028013
152146256
152165809
152199007
152199380
152199382
152213583
152246918
152255846
160644256
160644269
160644360
160644365
160654810
160661732
160800495
160963315
160963985
162010594
162010596
162164611
162164615
162164620
162164624
162175872
162546793
163309936
163309940
163309946
163309951
163309956
163309961
163309965
163309968
163309992
163632141
163632144
163632148
163632159
163805454
164187596
165235234
166223213
170465447
170481835
170482051
170482052
172088298
172096945
172097241
172818588
172818589
174476339
174560556
174560557
174861394
175267213
175442864
176484723
177900177
179116545
186014033
188627610
191112141
196679231
196679566
202542071
203105347
203105348
203355603
204380690
204938556
208011837
223399178
223448740
223448741
223448742
223493278
223543191
223704315
223755620
226393686
241102165
241107868
247624603
249828367
250014044
250204756
252091259
252157410
252165751
252166360
252214665
252300428
252344734
252344987
252400620
252401514
252403306
252452542
252824089
252824132
253663270
254761250
254761332
254801280
255386300
256401226
268734441
274086925
274951514
303072568
310262719
310262720
310263432
310265846
310265851
312225583
312523915
312695155
313076412
313080027
315668832
315668992
315673253
316392295
316892278
316892387
316892465
316892485
316900015
316905706
316919279
316920853
318151261
318151333
318160125
318172011
318344231
318464677
319102634
319102635
319102636
319459022
319886569
321934527
321949256
329591786
329731594
329747369
329748939
329770589
329823158
329824924
329829826
329847636
329847645
329847648
329973333
332875215
333494164
335039484
335990978
336285802
336285814
336286130
336295724
336943743
336943750
340081489
340088020
340098021
340470201
340471899
340515918
340555819
341139553
341199320
342526847
342580114
342582262
346400971
346693934
347758307
347831535
347912820
348274216
348355314
348355335
348355337
348438242
348479486
349140889
349980556
350088991
354266903
354302978
354332844
354349517
354349522
354349561
354349918
354350051
354702003
354702835
354974439
355159480
355199160
363321572
363593955
363900507
374017305
374168415
374364854
374403762
375079260
375134796
375136880
375555980
375573931
375573940
375574172
375635747
375684060
375983892
375984679
376011197
376152558
376163210
376171060
376171061
376171062
376171063
376195395
376219337
376227683
376353068
376860644
381000614
381007165
381025204
381117629
381119384
381119394
381119410
381133238
381327550
381364967
381647123
382372209
383147010
383470907
383861765
384256138
384405291
384568019
384571763
384653561
385147651
385153749
385645894
385793543
385980684
386045133
386187122
386294462
386466681
386482264
387021983
387060785
387133616
402316079
403033267
404418611
404721170
404748957
404758245
404827251
405041252
405057369
405057460
405231790
405558447
406183991
406514612
406800471
406800478
406842608
419507710
433774918
433776075
433776350
433776728
433776963
433777176
433777177
433777178
433777767
433780475
434131521
434139460
434293470
434295111
434482682
438444695
438474521
438474522
438505462
438568470
438630681
438652168
439442453
439593665
439641179
440064758
440076373
440787271
440790669
441087793
441119028
441294525
441562671
441579649
441654170
441657075
441657697
443507703
443534131
443534133
443548334
443623779

* 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
Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #0
Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #1
N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O tautomer #2
N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O tautomer #3
N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
A A A

* 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 mass267.0968
Average mass267.241
[M+H]+268.1046
Product ions136
Normalized LC elution time *1.43
LC elution order/characteristics not available

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

Reactions producing adenosine

Name
m6A:A

Reactions starting from adenosine

Name
A:t6A
A:hn6A
A:I
A:m6A
A:m1A
A:g6A
A:i6A
A:Am
A:m2A
A:Ar(p)
A:m8A

Last modification of this entry: Sept. 29, 2021


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