Summary

Full namearchaeosine
IUPAC name2-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
Short nameG+
MODOMICS code103G
Synonyms
148608-52-0
1H-Pyrrolo(2,3-d)pyrimidine-5-carboximidamide, 2-amino-4,7-dihydro-4-oxo-7-beta-D-ribofuranosyl-
2-amino-4,7-dihydro-4-oxo-7-beta-d-ribofuranosyl-1h-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
2-Amino-4,7-dihydro-4-oxo-7-beta-D-ribofuranosyl-1H-pyrrolo(2,3-d)pyrimidine-5-carboximidamide
2-amino-4-oxo-7-(beta-D-ribofuranosyl)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
2-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-1H-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
7-formamidino-7-deazaguanosine
AC1L31O3
Archaeosine
CHEBI:73271
CID132841
G*
Q632302

Nature of the modified residueNatural
RNAMods code(
Residue unique ID99
Found in RNAYes
Related nucleotides412
Enzymes ArcS (Methanocaldococcus jannaschii)
Found naturally in RNA typestRNA

Chemical information

Sum formulaC12H16N6O5
Type of moietynucleoside
Degeneracynot applicable
SMILESNc1[nH]c(=O)c2c(c[n]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)C(N)=N
logP-1.4164
TPSA196.49
Number of atoms23
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)10
Number of Hydrogen Bond Donors (HBD)7
PDB no exac match , link to the most similar ligand PQ1
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0011596
InChIInChI=1S/C12H16N6O5/c13-8(14)3-1-18(9-5(3)10(22)17-12(15)16-9)11-7(21)6(20)4(2-19)23-11/h1,4,6-7,11,19-21H,2H2,(H3,13,14)(H3,15,16,17,22)/t4-,6-,7-,11-/m1/s1
InChIKeyPEMQXWCOMFJRLS-RPKMEZRRSA-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
N=c1[nH]c(=O)c2c(cn(C3OC(CO)C(O)C3O)c2[nH]1)C(N)=N tautomer #0
Nc1nc(O)c2c(cn(C3OC(CO)C(O)C3O)c2n1)C(N)=N tautomer #1
Nc1nc(=O)c2c(cn(C3OC(CO)C(O)C3O)c2[nH]1)C(N)=N tautomer #2
Nc1[nH]c(=O)c2c(cn(C3OC(CO)C(O)C3O)c2n1)C(N)=N tautomer #3
N=c1[nH]c(O)c2c(cn(C3OC(CO)C(O)C3O)c2n1)C(N)=N tautomer #4
N=C1NC(=O)C2C(=CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #5
N=C1NC(=O)C2=C(CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #6
Nc1nc(O)c2c(cn(C3OC(CO)C(O)C3O)c2n1)C(N)=N tautomer #7
NC1=NC(=O)C2C(=CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #8
NC1=NC(=O)C2=C(CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #9
N=c1nc(O)c2c(cn(C3OC(CO)C(O)C3O)c2[nH]1)C(N)=N tautomer #10
N=C1N=C(O)C2C(=CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #11
N=C1N=C(O)C2=C(CN(C3OC(CO)C(O)C3O)C2=N1)C(N)=N tautomer #12

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
G+ G+ G+

* 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 mass324.1182
Average mass324.293
[M+H]+325.1255
Product ions193
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.

Comments

Positively charged under physiological pH. Alternative abbreviation: fa7d7G.

Reactions producing archaeosine

Name
preQ0:G+

Last modification of this entry: Sept. 29, 2021


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