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Details

Stereochemistry RACEMIC
Molecular Formula C5H8O5
Molecular Weight 148.114
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRAMALIC ACID

SMILES

CC(O)(CC(O)=O)C(O)=O

InChI

InChIKey=XFTRTWQBIOMVPK-UHFFFAOYSA-N
InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula C5H8O5
Molecular Weight 148.114
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolic flux analysis of the mixotrophic metabolisms in the green sulfur bacterium Chlorobaculum tepidum.
2010-12-10
A systems biology approach uncovers cellular strategies used by Methylobacterium extorquens AM1 during the switch from multi- to single-carbon growth.
2010-11-24
Metabolic response of Geobacter sulfurreducens towards electron donor/acceptor variation.
2010-11-22
Carbon flow of heliobacteria is related more to clostridia than to the green sulfur bacteria.
2010-11-05
The aconitate hydratase family from Citrus.
2010-10-19
Mild reductions in cytosolic NADP-dependent isocitrate dehydrogenase activity result in lower amino acid contents and pigmentation without impacting growth.
2010-10
Alternative isoleucine synthesis pathway in cyanobacterial species.
2010-02
The path to next generation biofuels: successes and challenges in the era of synthetic biology.
2010-01-20
Mild reductions in mitochondrial NAD-dependent isocitrate dehydrogenase activity result in altered nitrate assimilation and pigmentation but do not impact growth.
2010-01
Bridging the gap between fluxomics and industrial biotechnology.
2010
Synthetic biology guides biofuel production.
2010
1-methylmalate from camu-camu (Myrciaria dubia) suppressed D-galactosamine-induced liver injury in rats.
2010
Carbohydrate metabolism and carbon fixation in Roseobacter denitrificans OCh114.
2009-10-01
Features of structural organization and expression regulation of malate dehydrogenase isoforms from Rhodobacter sphaeroides strain 2R.
2009-07
[Enzymes of the citramalate cycle in Rhodospirillum rubrum].
2009-04-02
Dimethyl carbonate as potential reactant in non-catalytic biodiesel production by supercritical method.
2009-03
A versatile chiral selector for determination of enantiomeric composition of fluorescent and nonfluorescent chiral molecules using steady-state fluorescence spectroscopy.
2009-02
Applications of genome-scale metabolic reconstructions.
2009
Metabolic responses to salt stress of barley (Hordeum vulgare L.) cultivars, Sahara and Clipper, which differ in salinity tolerance.
2009
Metabolic characterization of loci affecting sensory attributes in tomato allows an assessment of the influence of the levels of primary metabolites and volatile organic contents.
2009
Molecular basis of the substrate specificity and the catalytic mechanism of citramalate synthase from Leptospira interrogans.
2008-10-01
Metabolism of halophilic archaea.
2008-03
The complete genome sequence and analysis of the epsilonproteobacterium Arcobacter butzleri.
2007-12-26
MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis.
2007-05
A comprehensive survey on isoleucine biosynthesis pathways in seven epidemic Leptospira interrogans reference strains of China.
2007-04
[The mechanism of acetate assimilation in purple nonsulfur bacteria lacking the glyoxylate pathway: enzymes of the citramalate cycle in Rhodobacter sphaeroides].
2005-08-27
[The mechanism of acetate assimilation in purple nonsulfur bacteria lacking the glyoxylate pathway: acetate assimilation in Rhodobacter sphaeroides cells].
2005-08-27
Inhibition of acetate and propionate assimilation by itaconate via propionyl-CoA carboxylase in isocitrate lyase-negative purple bacterium Rhodospirillum rubrum.
2002-10-29
A bicyclic autotrophic CO2 fixation pathway in Chloroflexus aurantiacus.
2002-06-07
Significance of two distinct types of tryptophan synthase beta chain in Bacteria, Archaea and higher plants.
2002
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 22:09:17 GMT 2025
Edited
by admin
on Mon Mar 31 22:09:17 GMT 2025
Record UNII
FGC721P65H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-80648
Preferred Name English
CITRAMALIC ACID
MI  
Systematic Name English
CITRAMALIC ACID [MI]
Common Name English
(±)-CITRAMALIC ACID
Systematic Name English
(±)-.ALPHA.-METHYLMALIC ACID
Common Name English
2-HYDROXY-2-METHYLBUTANEDIOIC ACID
Systematic Name English
(±)-2-METHYLMALIC ACID
Systematic Name English
CITRAMALIC ACID, (±)-
Common Name English
DL-CITRAMALIC ACID
Common Name English
BUTANEDIOIC ACID, 2-HYDROXY-2-METHYL-
Systematic Name English
2-DEOXY-3-C-METHYLTETRARIC ACID
Common Name English
Code System Code Type Description
FDA UNII
FGC721P65H
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID40862265
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
PUBCHEM
1081
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-901-5
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
CAS
597-44-4
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
MERCK INDEX
m3592
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY Merck Index
NSC
80648
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY
CHEBI
15584
Created by admin on Mon Mar 31 22:09:17 GMT 2025 , Edited by admin on Mon Mar 31 22:09:17 GMT 2025
PRIMARY