Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:50:36 UTC
Update Date2022-08-31 17:38:39 UTC
Metabolite IDMMDBc0030011
Metabolite Identification
Common Name4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol
Description4-(cytidine 5'-diphospho)-2-c-methyl-D-erythritol is a member of the chemical class known as Pyrimidine Ribonucleoside Diphosphates. These are pyrimidine ribobucleotides with diphosphate group linked to the ribose moiety. CDP-ME is an intermediate in the mevalonate-independent pathway for isoprenoid biosynthesis in a number of prokaryotic organisms, algae, the plant plastids and the malaria parasite. (PMID 11427897 ) In the MEP pathway, 4-diphosphocytidyl-2-C-methyl-D-erythritol is formed from 2-C-methyl-D-erythritol 4-phosphate (MEP) and CTP in a reaction catalyzed by a 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (IspD). (PMID 17921290 ) Diphosphocytidyl-methylerythritol (DPCME) synthetase is involved in the mevalonate-independent pathway of isoprenoid biosynthesis, where it catalyses the formation of 4-diphosphocytidyl-2-C-methyl-D-erythritol from 2-C-methyl-D-erythritol 4-phosphate and CTP. (PMID 11468415 )
Structure
Synonyms
ValueSource
4-CDP-2-C-Methyl-D-erythritolChEBI
4-CDP-2-C-Methyl-D-erythritol dianionChEBI
5'-O-{[({[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl]oxy}phosphinato)oxy]phosphinato}cytidineChEBI
4-DPCMEMeSH
4-Diphosphocytidyl-2-C-methylerythritolMeSH
4-Diphosphocytidyl-2C-methyl-D-erythritolMeSH
Molecular FormulaC14H23N3O14P2
Average Mass519.294
Monoisotopic Mass519.066623588
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[(2R,3S)-2,3,4-trihydroxy-3-methylbutoxy]phosphoryl phosphono}oxy)methyl]oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate
Traditional Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy((2R,3S)-2,3,4-trihydroxy-3-methylbutoxy)phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-4-iminopyrimidin-2-olate
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COP(O)(=O)OP([O-])(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])O)[C@@](C)(O)CO
InChI Identifier
InChI=1S/C14H25N3O14P2/c1-14(23,6-18)8(19)5-29-33(26,27)31-32(24,25)28-4-7-10(20)11(21)12(30-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21,23H,4-6H2,1H3,(H,24,25)(H,26,27)(H2,15,16,22)/p-2/t7-,8-,10-,11-,12-,14+/m1/s1
InChI KeyYFAUKWZNPVBCFF-XHIBXCGHSA-L