Summary

Full nameadenosine-5'-monophosphate
IUPAC name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Short namepA
MODOMICS code551A
Synonyms
2gmk
2q8m
2qrk
[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-2-oxolanyl]methyl phosphate
2vfk
3dhv
3tdh
4g0y
5'-adenosine monophosphate
5'-adenylic acid
5'-AMP
5'-O-phosphonatoadenosine
6042-43-9
61-19-8
A833090
adenosine 5'-monophosphate
adenosine 5'-monophosphate dianion
adenosine 5'-monophosphate(2-)
adenosine 5'-phosphate
Adenosine-5-monophosphate
Adenosine-5-monophosphate dianion
Adenosine-5-monophosphate(2-)
adenosine-monophosphate
adenylate
adenylic acid
AMP
AMP dianion
AMP(2-)
BDBM50192453
CHEBI:456215
CID15938965
CJ-10834
LDHA Inhibitor, 6
nchembio867-comp5
Q27225747
TL8003885
VIDARABINE PHOSPHATE

Nature of the modified residueNatural
Residue unique ID444
Related nucleosides109
RCSB ligands

Chemical information

Sum formulaC10H12N5O7P
Type of moietynucleotide
SMILESNc1c2c([n]([C@H]3[C@H](O)[C@H](O)[C@@H](COP(=O)([O-])[O-])O3)cn2)ncn1
logP-0.4054
TPSA201.54
Number of atoms23
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)12
Number of Hydrogen Bond Donors (HBD)3
InChIInChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1
InChIKeyUDMBCSSLTHHNCD-KQYNXXCUSA-L
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
Nc1c2c(n(C3C(O)C(O)C(COP(=O)([O-])[O-])O3)cn2)ncn1 tautomer #0
Nc1c2c(n(C3C(O)C(O)C(COP(=O)([O-])[O-])O3)cn2)ncn1 tautomer #1
N=c1c2c(n(C3C(O)C(O)C(COP(=O)([O-])[O-])O3)cn2)[nH]cn1 tautomer #2
N=c1c2c(n(C3C(O)C(O)C(COP(=O)([O-])[O-])O3)cn2)nc[nH]1 tautomer #3
N=C1C2C(N(C3C(O)C(O)C(COP(=O)([O-])[O-])O3)C=N2)=NC=N1 tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
pA pA pA

* 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 massNone
Average mass345.205
[M+H]+ not available
Product ions not available
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.

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca