Full name2- methylthiomethylenethio-N6-isopentenyl-adenosine-5'-monophosphate
Short namepmsms2i6A
MODOMICS code21161551A
Nature of the modified residueNatural
Residue unique ID372
Related nucleosides182
RCSB ligands

Chemical information

Sum formulaC17H24N5O7PS2
Type of moietynucleotide
Number of atoms32
Number of Hydrogen Bond Acceptors 1 (HBA1)11
Number of Hydrogen Bond Acceptors 2 (HBA2)14
Number of Hydrogen Bond Donors (HBD)3
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 

* 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 SMILES
CSCSc1nc(NCC=C(C)C)c2ncn(C3OC(COP(=O)([O-])[O-])C(O)C3O)c2n1 tautomer #0
CSCSc1nc(NCC=C(C)C)c2ncn(C3OC(COP(=O)([O-])[O-])C(O)C3O)c2n1 tautomer #1
CSCSc1nc(=NCC=C(C)C)c2ncn(C3OC(COP(=O)([O-])[O-])C(O)C3O)c2[nH]1 tautomer #2
CSCSc1[nH]c(=NCC=C(C)C)c2ncn(C3OC(COP(=O)([O-])[O-])C(O)C3O)c2n1 tautomer #3
CSCSC1=NC(=NCC=C(C)C)C2N=CN(C3OC(COP(=O)([O-])[O-])C(O)C3O)C2=N1 tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

pmsms2i6A pmsms2i6A pmsms2i6A

* 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 mass505.506
[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

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