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Showing metabocard for Ethylmalonic acid (HMDB0000622)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:59 UTC
HMDB IDHMDB0000622
Secondary Accession Numbers
  • HMDB00622
Metabolite Identification
Common NameEthylmalonic acid
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000622 (Ethylmalonic acid)

  Mrv1652303162022072D          

  9  8  0  0  0  0            999 V2000
   -0.7145    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  8  9  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
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3D MOL for HMDB0000622 (Ethylmalonic acid)

HMDB0000622
     RDKit          3D
Ethylmalonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1034    0.5785   -0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0448   -0.4024   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2054   -0.2623    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096   -1.2478   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427   -2.0303   -1.2147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -1.3146    0.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0639    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    1.9697   -0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    1.3573    0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067    0.1303   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9682    0.8067    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    1.4958   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.4254   -0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -0.3659   -1.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -0.4941    1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129   -2.0834    0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1824    2.2241    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0000622 (Ethylmalonic acid)

  Mrv1652303162022072D          

  9  8  0  0  0  0            999 V2000
   -0.7145    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  8  9  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000622

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)

> <INCHI_KEY>
UKFXDFUAPNAMPJ-UHFFFAOYSA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.1146

> <EXACT_MASS>
132.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.976514317112754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethylpropanedioic acid

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.6564376749999998

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.580590600104313

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.495963643151088

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.1633

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethylmalonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000622 (Ethylmalonic acid)

HMDB0000622
     RDKit          3D
Ethylmalonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1034    0.5785   -0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0448   -0.4024   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2054   -0.2623    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096   -1.2478   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427   -2.0303   -1.2147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -1.3146    0.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0639    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    1.9697   -0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    1.3573    0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067    0.1303   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9682    0.8067    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    1.4958   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.4254   -0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -0.3659   -1.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -0.4941    1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129   -2.0834    0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1824    2.2241    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0000622 (Ethylmalonic acid)

HEADER    PROTEIN                                 16-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    6    7                                                  
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    9    2                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000622 (Ethylmalonic acid)

COMPND    HMDB0000622
HETATM    1  C1  UNL     1       2.103   0.579  -0.162  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.045  -0.402  -0.604  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.205  -0.262   0.205  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.210  -1.248  -0.270  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.943  -2.030  -1.215  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.461  -1.315   0.328  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.806   1.064   0.156  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.274   1.970  -0.525  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.961   1.357   0.846  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.107   0.130  -0.358  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.968   0.807   0.915  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.002   1.496  -0.761  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.463  -1.425  -0.379  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.887  -0.366  -1.691  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.080  -0.494   1.273  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.613  -2.083   0.965  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.182   2.224   1.276  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    7   15
CONECT    4    5    5    6
CONECT    6   16
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for HMDB0000622 (Ethylmalonic acid)

CCC(C(O)=O)C(O)=O
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INCHI for HMDB0000622 (Ethylmalonic acid)

InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,1-Propanedicarboxylic acidChEBI
2-Ethylmalonic acidChEBI
alpha-Carboxybutyric acidChEBI
1,1-PropanedicarboxylateGenerator
2-EthylmalonateGenerator
a-CarboxybutyrateGenerator
a-Carboxybutyric acidGenerator
alpha-CarboxybutyrateGenerator
Α-carboxybutyrateGenerator
Α-carboxybutyric acidGenerator
EthylmalonateGenerator
Ethyl-malonic acidHMDB
2-Ethylpropanedioic acidHMDB
Ethylmalonic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
IUPAC Name2-ethylpropanedioic acid
Traditional Nameethylmalonic acid
CAS Registry Number601-75-2
SMILES
CCC(C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyUKFXDFUAPNAMPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial applicationIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point112 - 114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility712 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Placenta
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Malonyl-Coa decarboxylase deficiency
  1. Yano S, Sweetman L, Thorburn DR, Mofidi S, Williams JC: A new case of malonyl coenzyme A decarboxylase deficiency presenting with cardiomyopathy. Eur J Pediatr. 1997 May;156(5):382-3. [PubMed:9177981 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Ethylmalonic encephalopathy
  1. Di Rocco M, Caruso U, Briem E, Rossi A, Allegri AE, Buzzi D, Tiranti V: A case of ethylmalonic encephalopathy with atypical clinical and biochemical presentation. Mol Genet Metab. 2006 Dec;89(4):395-7. Epub 2006 Jul 7. [PubMed:16828325 ]
Short Chain Acyl-Coa Dehydrogenase Deficiency
  1. Amendt BA, Greene C, Sweetman L, Cloherty J, Shih V, Moon A, Teel L, Rhead WJ: Short-chain acyl-coenzyme A dehydrogenase deficiency. Clinical and biochemical studies in two patients. J Clin Invest. 1987 May;79(5):1303-9. [PubMed:3571488 ]
  2. Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
  3. Oglesbee D, He M, Majumder N, Vockley J, Ahmad A, Angle B, Burton B, Charrow J, Ensenauer R, Ficicioglu CH, Keppen LD, Marsden D, Tortorelli S, Hahn SH, Matern D: Development of a newborn screening follow-up algorithm for the diagnosis of isobutyryl-CoA dehydrogenase deficiency. Genet Med. 2007 Feb;9(2):108-16. doi: 10.1097GIM.0b013e31802f78d6. [PubMed:17304052 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Gregersen N, Kolvraa S, Rasmussen K, Mortensen PB, Divry P, David M, Hobolth N: General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases. Clin Chim Acta. 1983 Aug 15;132(2):181-91. [PubMed:6616873 ]
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Thompson GN, Hsu BY, Pitt JJ, Treacy E, Stanley CA: Fasting hypoketotic coma in a child with deficiency of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. N Engl J Med. 1997 Oct 23;337(17):1203-7. doi: 10.1056/NEJM199710233371704. [PubMed:9337379 ]
Isobutyryl-CoA Dehydrogenase Deficiency
  1. Oglesbee D, He M, Majumder N, Vockley J, Ahmad A, Angle B, Burton B, Charrow J, Ensenauer R, Ficicioglu CH, Keppen LD, Marsden D, Tortorelli S, Hahn SH, Matern D: Development of a newborn screening follow-up algorithm for the diagnosis of isobutyryl-CoA dehydrogenase deficiency. Genet Med. 2007 Feb;9(2):108-16. doi: 10.1097GIM.0b013e31802f78d6. [PubMed:17304052 ]
Associated OMIM IDs
  • 606788 (Anorexia nervosa)
  • 248360 (Malonyl-Coa decarboxylase deficiency)
  • 610247 (Eosinophilic esophagitis)
  • 602473 (Ethylmalonic encephalopathy)
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
  • 611283 (Isobutyryl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022147
KNApSAcK IDC00052274
Chemspider ID11263
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4180
PubChem Compound11756
PDB IDNot Available
ChEBI ID741548
Food Biomarker OntologyNot Available
VMH IDETHMALAC
MarkerDB IDMDB00000204
Good Scents IDrw1246381
References
Synthesis ReferenceZakharova, T. V.; Ternovaya, T. V.; Pirkes, S. B.; Kostromina, N. A. Study of complexing in the neodymium-ethylmalonic acid system by a spectrographic method. Zhurnal Neorganicheskoi Khimii (1979), 24(7), 1827-31.
Material Safety Data Sheet (MSDS)Not Available
General References