Modomics - A Database of RNA Modifications

The molecule is shown in a ball-and-stick representation with the following colors for atoms :
Hydrogen (H): white Carbon (C): gray Oxygen (O): red Phosphorus (P): orange Nitrogen (N): blue Selenium (Se): gold Sulfur (S): yellow

Summary

Full name3-(3-amino-3-carboxypropyl)methyluridine
Short nameacp3Um
MODOMICS code new
MODOMICS code15U
Nature of the modified residueNatural
RNAMods code
Residue unique ID53

Chemical information

Sum formulaC14H21N3O8
Type of moietynucleoside
SMILESCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1c(=O)n(CCC(C(=O)O)N)c(=O)cc1
logP-2.2221
TPSA166.24
Number of atoms25
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)11
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand URI
HMDB (Human Metabolome Database) no exact match, link to the most similar ligand None
InChIInChI=1S/C14H21N3O8/c1-24-11-10(20)8(6-18)25-12(11)17-5-3-9(19)16(14(17)23)4-2-7(15)13(21)22/h3,5,7-8,10-12,18,20H,2,4,6,15H2,1H3,(H,21,22)/t7?,8-,10-,11-,12-/m1/s1
InChIKeyXIDMMDKYGHCYDT-BYVZJJQMSA-N
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

Tautomers SMILES
COC1C(O)C(CO)OC1n2c(=O)n(CCC(C(=O)O)N)c(=O)cc2 acp3Um tautomer #0
COC1C(O)C(CO)OC1n2c(=O)n(CCC(C(O)O)=N)c(=O)cc2 acp3Um tautomer #1
COC1C(O)C(CO)OC1n2c(=O)n(CC=C(C(O)O)N)c(=O)cc2 acp3Um tautomer #2
COC1C(O)C(CO)OC1n2c(=O)n(CCC(=C(O)O)N)c(=O)cc2 acp3Um tautomer #3
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
acp3Um acp3Um acp3Um

* 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 mass359.1329
Average mass359.332
[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.

Chemical groups contained

TypeSubtype
aminoacyl groupaspartyl
methyl groupmethyl at O2

Reactions producing 3-(3-amino-3-carboxypropyl)methyluridine

Name
acp3U:acp3Um

Last modification of this entry: July 27, 2023