Summary

Full name1-methyl-3-(3-amino-3-carboxypropyl)pseudouridine
IUPAC name2-amino-4-[5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-2,6-dioxopyrimidin-1-yl]butanoic acid
Short namem1acp3Y
MODOMICS code1309U
Synonyms
1(2H)-Pyrimidinebutanoic acid, alpha-amino-3,6-dihydro-3-methyl-2,6-dioxo-5-beta-D-ribofuranosyl-
1-methyl-3-(3-amino-3-carboxypropyl)pseudouridine
1-Methyl-3-(3-carboxy-3-aminopropyl)-5-(beta-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione
(1s)-1-[3-(3-amino-3-carboxypropyl)-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]-1,4-anhydro-d-ribitol
2-amino-4-[5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-2,6-dioxopyrimidin-1-yl]butanoic acid
3-(3-Amino-3-carboxypropyl)-1-methylpseudouridine
52777-29-4
56889-16-8
AC1L4X6W
AC1Q5S8C
Acpmpsu
AR-1A1392
CID193882
DTXSID20276725
KST-1A6118
SCHEMBL1067194
Nature of the modified residueNatural
RNAMods codeα
Residue unique ID8
Found in RNAYes
Related nucleotides343
Found naturally in RNA typesrRNA

Chemical information

Sum formulaC14H21N3O8
Type of moietynucleoside
Degeneracynot applicable
SMILESC[n]1c(=O)[n](CCC(C(=O)O)N)c(=O)c([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)c1
logP-2.7967
TPSA177.24
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)5
PDB no exac match , link to the most similar ligand B8N
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000767
InChIInChI=1S/C14H21N3O8/c1-16-4-6(11-10(20)9(19)8(5-18)25-11)12(21)17(14(16)24)3-2-7(15)13(22)23/h4,7-11,18-20H,2-3,5,15H2,1H3,(H,22,23)/t7?,8-,9-,10-,11+/m1/s1
InChIKeyCTPQMQZKRWLMRA-LYTXVXJPSA-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
Cn1c(=O)n(CCC(C(O)=O)N)c(=O)c(C2C(O)C(O)C(CO)O2)c1 tautomer #0
Cn1c(=O)n(CCC(C(O)O)=N)c(=O)c(C2C(O)C(O)C(CO)O2)c1 tautomer #1
Cn1c(=O)n(CC=C(C(O)O)N)c(=O)c(C2C(O)C(O)C(CO)O2)c1 tautomer #2
Cn1c(=O)n(CCC(=C(O)O)N)c(=O)c(C2C(O)C(O)C(CO)O2)c1 tautomer #3
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m1acp3Y m1acp3Y m1acp3Y

* 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]+360.1407
Product ions228
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 aromatic N

Reactions producing 1-methyl-3-(3-amino-3-carboxypropyl)pseudouridine

Name
m1Y:m1acp3Y

Last modification of this entry: Sept. 29, 2021


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