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Showing metabocard for Methylsuccinic acid (HMDB0001844)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-02 11:25:17 UTC
Update Date2023-02-21 17:15:49 UTC
HMDB IDHMDB0001844
Secondary Accession Numbers
  • HMDB01844
Metabolite Identification
Common NameMethylsuccinic acid
DescriptionMethylsuccinic acid (CAS: 498-21-5) is a normal metabolite found in human fluids. Increased urinary levels of methylsuccinic acid (together with ethylmalonic acid) are the main biochemical measurable features in ethylmalonic encephalopathy (OMIM: 602473 ), a rare metabolic disorder with an autosomal recessive mode of inheritance that is clinically characterized by neuromotor delay, hyperlactic acidemia, recurrent petechiae, orthostatic acrocyanosis, and chronic diarrhea (PMID:12382164 ). The underlying biochemical defect involves isoleucine catabolism (PMID:9667231 ). Methylsuccinic acid levels were found to have decreased in the urine of animals under D-serine-induced nephrotoxicity (D-serine causes selective necrosis of the proximal straight tubules in the rat kidney) (PMID:15596249 ). Moreover, methylsuccinic acid is found to be associated with ethylmalonic encephalopathy, isovaleric acidemia, and medium-chain acyl-CoA dehydrogenase deficiency, which are also inborn errors of metabolism.
Structure
Data?1676999749
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001844 (Methylsuccinic acid)


  Mrv1652303172016322D          

  9  8  0  0  1  0            999 V2000
    1.7069   -0.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -0.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778   -0.0228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4366   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    0.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511   -0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for HMDB0001844 (Methylsuccinic acid)

HMDB0001844
     RDKit          3D
Methylsuccinic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.9049   -0.8327   -0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4240    0.4564    0.0334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9668    0.2498    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9147   -0.1302   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.7916   -1.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -1.4387   -0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818    0.7655    1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    0.8438    2.2975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7169    0.9564    0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727   -1.7283   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112   -0.9222   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -0.8798   -1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    1.2222   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    1.2152    1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665   -0.5182    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1390   -1.6380   -1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    1.5873    0.0660 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
  2  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  6
  3 14  1  0
  3 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0001844 (Methylsuccinic acid)


  Mrv1652303172016322D          

  9  8  0  0  1  0            999 V2000
    1.7069   -0.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -0.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778   -0.0228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4366   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    0.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511   -0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001844

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/t3-/m0/s1

> <INCHI_KEY>
WXUAQHNMJWJLTG-VKHMYHEASA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.115

> <EXACT_MASS>
132.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.866190114358801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-methylbutanedioic acid

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.14450331100000002

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.578119667709393

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9897992068502925

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.1115

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-methylbutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001844 (Methylsuccinic acid)

HMDB0001844
     RDKit          3D
Methylsuccinic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.9049   -0.8327   -0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4240    0.4564    0.0334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9668    0.2498    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9147   -0.1302   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.7916   -1.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -1.4387   -0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818    0.7655    1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    0.8438    2.2975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7169    0.9564    0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727   -1.7283   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112   -0.9222   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -0.8798   -1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    1.2222   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    1.2152    1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665   -0.5182    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1390   -1.6380   -1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    1.5873    0.0660 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
  2  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  6
  3 14  1  0
  3 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0001844 (Methylsuccinic acid)

HEADER    PROTEIN                                 17-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAR-20         0                                  
HETATM    1  O   UNK     0       3.186  -0.043   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -3.483  -0.813   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.852  -2.353   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.149   1.497   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.519  -0.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.815  -0.813   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.519   1.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.852  -0.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.149  -0.043   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    8                                                            
CONECT    4    9                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9                                                       
CONECT    7    5                                                            
CONECT    8    1    3    5                                                  
CONECT    9    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0001844 (Methylsuccinic acid)

COMPND    HMDB0001844
HETATM    1  C1  UNL     1       0.905  -0.833  -0.617  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.424   0.456   0.033  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.967   0.250   0.604  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.915  -0.130  -0.469  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.366   0.792  -1.230  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.323  -1.439  -0.673  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.382   0.765   1.129  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.965   0.844   2.297  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.717   0.956   0.800  1.00  0.00           O  
HETATM   10  H1  UNL     1       0.473  -1.728  -0.111  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.011  -0.922  -0.542  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.661  -0.880  -1.700  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.427   1.222  -0.764  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.314   1.215   1.007  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.967  -0.518   1.398  1.00  0.00           H  
HETATM   16  H7  UNL     1      -3.139  -1.638  -1.229  1.00  0.00           H  
HETATM   17  H8  UNL     1       3.025   1.587   0.066  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    7   13
CONECT    3    4   14   15
CONECT    4    5    5    6
CONECT    6   16
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for HMDB0001844 (Methylsuccinic acid)

C[C@@H](CC(O)=O)C(O)=O
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INCHI for HMDB0001844 (Methylsuccinic acid)

InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-Methylbutanedioic acidChEBI
(S)-2-MethylbutanedioateGenerator
MethylsuccinateGenerator
(S)-MethylsuccinateHMDB
(-)-(2S)-Methylbutanedioic acidHMDB
(-)-(S)-alpha-Methylsuccinic acidHMDB
(-)-(S)-Α-methylsuccinic acidHMDB
(-)-2-Methylsuccinic acidHMDB
(-)-Methylsuccinic acidHMDB
(-)-alpha-Methylsuccinic acidHMDB
(-)-Α-methylsuccinic acidHMDB
(2S)-2-Methylbutanedioic acidHMDB
(2S)-Methylbutanedioic acidHMDB
(S)-(-)-2-Methylsuccinic acidHMDB
(S)-(-)-Methylsuccinic acidHMDB
(S)-2-Methylsuccinic acidHMDB
(S)-Methylsuccinic acidHMDB
(S)-alpha-Methylsuccinic acidHMDB
(S)-Α-methylsuccinic acidHMDB
1,2-Propanedicarboxylic acidHMDB
2-Methylbutane-1,4-dioic acidHMDB
2-Methylbutanedioic acidHMDB
2-Methylsuccinic acidHMDB
Methylbutanedioic acidHMDB
Pyrotartaric acidHMDB
alpha-Methylsuccinic acidHMDB
Α-methylsuccinic acidHMDB
Methylsuccinic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.115
Monoisotopic Molecular Weight132.042258738
IUPAC Name(2S)-2-methylbutanedioic acid
Traditional Name(2S)-2-methylbutanedioic acid
CAS Registry Number2174-58-5
SMILES
C[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/t3-/m0/s1
InChI KeyWXUAQHNMJWJLTG-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • 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 DescriptorsNot Available
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility516.5 mg/mLHuman Metabolome Project
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker124.330932474
[M-H]-Not Available124.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00001894
Predicted Molecular Properties
PropertyValueSource
Water Solubility103 g/LALOGPS
logP0.13ALOGPS
logP0.14ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.11 m³·mol⁻¹ChemAxon
Polarizability11.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+123.91130932474
DeepCCS[M-H]-120.04430932474
DeepCCS[M-2H]-157.55830932474
DeepCCS[M+Na]+132.87630932474
AllCCS[M+H]+131.032859911
AllCCS[M+H-H2O]+126.932859911
AllCCS[M+NH4]+134.932859911
AllCCS[M+Na]+136.032859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-128.632859911
AllCCS[M+HCOO]-131.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.73 minutes32390414
Predicted by Siyang on May 30, 20229.4645 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.83 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid224.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid970.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid337.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid65.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid199.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid59.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid269.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid290.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)174.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid605.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid175.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid832.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid209.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid247.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate632.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA249.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water368.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methylsuccinic acidC[C@@H](CC(O)=O)C(O)=O1992.6Standard polar33892256
Methylsuccinic acidC[C@@H](CC(O)=O)C(O)=O991.4Standard non polar33892256
Methylsuccinic acidC[C@@H](CC(O)=O)C(O)=O1261.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylsuccinic acid,1TMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C)C(=O)O1252.5Semi standard non polar33892256
Methylsuccinic acid,1TMS,isomer #2C[C@@H](CC(=O)O)C(=O)O[Si](C)(C)C1224.5Semi standard non polar33892256
Methylsuccinic acid,2TMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1340.9Semi standard non polar33892256
Methylsuccinic acid,1TBDMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1493.5Semi standard non polar33892256
Methylsuccinic acid,1TBDMS,isomer #2C[C@@H](CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1472.4Semi standard non polar33892256
Methylsuccinic acid,2TBDMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1762.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methylsuccinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0910000000-b99795b0e5069d573c2d2020-03-17HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylsuccinic acid EI-B (Non-derivatized)splash10-0002-0920000000-c96774045667ea1804df2020-03-17HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylsuccinic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-b99795b0e5069d573c2d2020-03-17HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylsuccinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0077-9000000000-1bd08b69cec7f9966cb22020-03-17Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-3900000000-4afd6f9cd1309a7a392b2020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kr-9600000000-e212a368f465b41cc1fa2020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0l0i-9200000000-c712b36382fde51f3ae52020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-9400000000-f709b1c905420a0060382020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0019-9400000000-40a1055d8102e323a0772020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-9400000000-f709b1c905420a0060382020-03-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylsuccinic acid LC-ESI-QTOF , negative-QTOFsplash10-0019-9400000000-40a1055d8102e323a0772020-03-17HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 10V, Negative-QTOFsplash10-000i-9300000000-ae74d9b2b9c67b6b2c032021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 20V, Negative-QTOFsplash10-000i-9000000000-752373f081439a3a1c1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 40V, Negative-QTOFsplash10-0006-9000000000-b7e72688d4147a54e2f12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 10V, Positive-QTOFsplash10-014r-9400000000-75023a5f4028426602922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 20V, Positive-QTOFsplash10-00kf-9000000000-6b61132784740ec745582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylsuccinic acid 40V, Positive-QTOFsplash10-0006-9000000000-99524f95f29b02f6a6762021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2020-03-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-03-17Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified151.384 +/- 209.666 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified81.520 +/- 46.853 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified8.04 +/- 0.4 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified0.900 +/- 0.800 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified5 +/- 3 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2-3 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified<3.392 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.899 +/- 3.586 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified<2.0 umol/mmol creatinineChildren (1-13 years old)MaleNormal details
UrineDetected and Quantified1.900 +/- 0.700 umol/mmol creatinineChildren (1 - 13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified<3.392 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0-1.9 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified0-3.0 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified0-3.1 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified0-5.3 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.8 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2.8 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2.6 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.3 (0.8-10.8) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.06 +/- 0.99 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified4.7 (1.1-6.2) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.2 (0.7-9.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.53-0.85 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.56 +/- 1.12 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified2.7 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified1.065 +/- 0.863 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified<3.89 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0.69-1.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified1.100-5.900 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
isovaleric acidemia		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified22.612-101.754 umol/mmol creatinineNewborn (0-30 days old)FemaleShort Chain Acyl-Coa Dehydrogenase Deficiency details
UrineDetected and Quantified6-630 umol/mmol creatinineInfant (0-1 year old)Both
Short chain acyl-CoA Dehydrogenase deficiency (SCAD)		 details
UrineDetected and Quantified5.200-62.500 umol/mmol creatinineInfant (0-1 year old)Not Specified
isovaleric acidemia		 details
UrineDetected and Quantified3-9 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected and Quantified22.612-101.754 umol/mmol creatinineInfant (0-1 year old)Female
Short chain acyl-CoA dehydrogenase deficiency (SCAD)		 details
UrineDetected and Quantified11.400-17.300 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
isovaleric acidemia		 details
UrineDetected and Quantified1.9 (1.3-2.5) umol/mmol creatinineAdult (>18 years old)BothRefsum's disease details
UrineDetected and Quantified0.900-16.700 umol/mmol creatinineInfant (0-1 year old)Not Specified
isovaleric acidemia		 details
UrineDetected and Quantified7.2 umol/mmol creatinineChildren (1-13 years old)MaleEthylmalonic encephalopathy details
UrineDetected and Quantified1.628 +/- 1.644 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected and Quantified25.309 +/- 83.321 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified6.467 +/- 5.597 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified2.81 +/- 0.57 umol/mmol creatinineChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Refsum's disease
  1. Greter J, Lindstedt S, Steen G: 2,6-Dimethyloctanedioic acid--a metabolite of phytanic acid in Refsum's disease. Clin Chem. 1983 Mar;29(3):434-7. [PubMed:6186413 ]
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 ]
Isovaleric acidemia
  1. Loots DT: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. J Inherit Metab Dis. 2009 Jun;32(3):403-11. doi: 10.1007/s10545-009-1071-6. Epub 2009 Apr 5. [PubMed:19343532 ]
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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022704
KNApSAcK IDC00052350
Chemspider ID5323413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylsuccinic acid
METLIN IDNot Available
PubChem Compound6950476
PDB IDNot Available
ChEBI ID91316
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000343
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  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. Grosso S, Mostardini R, Farnetani MA, Molinelli M, Berardi R, Dionisi-Vici C, Rizzo C, Morgese G, Balestri P: Ethylmalonic encephalopathy: further clinical and neuroradiological characterization. J Neurol. 2002 Oct;249(10):1446-50. [PubMed:12382164 ]
  4. Nowaczyk MJ, Lehotay DC, Platt BA, Fisher L, Tan R, Phillips H, Clarke JT: Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism. 1998 Jul;47(7):836-9. [PubMed:9667231 ]
  5. Williams RE, Major H, Lock EA, Lenz EM, Wilson ID: D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach. Toxicology. 2005 Feb 14;207(2):179-90. [PubMed:15596249 ]