MiMeDB: Showing metabocard for Methylsuccinic acid (MMDBc0000392)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:45 UTC

Update Date

2024-04-30 19:32:06 UTC

Metabolite ID

MMDBc0000392

Metabolite Identification

Common Name

Methylsuccinic acid

Description

Methylsuccinic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Methylbutanedioic acid	ChEBI
(S)-2-Methylbutanedioate	Generator
Methylsuccinate	Generator
(S)-Methylsuccinate	HMDB
(-)-(2S)-Methylbutanedioic acid	HMDB
(-)-(S)-alpha-Methylsuccinic acid	HMDB
(-)-(S)-Α-methylsuccinic acid	HMDB
(-)-2-Methylsuccinic acid	HMDB
(-)-Methylsuccinic acid	HMDB
(-)-alpha-Methylsuccinic acid	HMDB
(-)-Α-methylsuccinic acid	HMDB
(2S)-2-Methylbutanedioic acid	HMDB
(2S)-Methylbutanedioic acid	HMDB
(S)-(-)-2-Methylsuccinic acid	HMDB
(S)-(-)-Methylsuccinic acid	HMDB
(S)-2-Methylsuccinic acid	HMDB
(S)-Methylsuccinic acid	HMDB
(S)-alpha-Methylsuccinic acid	HMDB
(S)-Α-methylsuccinic acid	HMDB
1,2-Propanedicarboxylic acid	HMDB
2-Methylbutane-1,4-dioic acid	HMDB
2-Methylbutanedioic acid	HMDB
2-Methylsuccinic acid	HMDB
Methylbutanedioic acid	HMDB
Pyrotartaric acid	HMDB
alpha-Methylsuccinic acid	HMDB
Α-methylsuccinic acid	HMDB
Methylsuccinic acid	HMDB

Molecular Formula

C₅H₈O₄

Average Mass

132.115

Monoisotopic Mass

132.042258738

IUPAC Name

(2S)-2-methylbutanedioic acid

Traditional Name

(2S)-2-methylbutanedioic acid

CAS Registry Number

Not Available

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.14	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.11 m³·mol⁻¹	ChemAxon
Polarizability	11.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0910000000-b99795b0e5069d573c2d	2020-03-17	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0920000000-c96774045667ea1804df	2020-03-17	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-b99795b0e5069d573c2d	2020-03-17	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9400000000-f709b1c905420a006038	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0019-9400000000-40a1055d8102e323a077	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9400000000-f709b1c905420a006038	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0019-9400000000-40a1055d8102e323a077	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-3900000000-4afd6f9cd1309a7a392b	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-9600000000-e212a368f465b41cc1fa	2020-03-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0l0i-9200000000-c712b36382fde51f3ae5	2020-03-17	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9300000000-ae74d9b2b9c67b6b2c03	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-752373f081439a3a1c1d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b7e72688d4147a54e2f1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-9400000000-75023a5f402842660292	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-6b61132784740ec74558	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-99524f95f29b02f6a676	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0077-9000000000-1bd08b69cec7f9966cb2	2020-03-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2020-03-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2020-03-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)		2020-03-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2020-03-17	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008656	Methyl-Succinyl Coenzyme A	Methylsuccinic acid	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Ethylmalonic encephalopathy	Increased	Association	Human Urine	HMDB	16828325
Isovaleric acidemia		Association	Human Urine	HMDB	19343532
Medium chain acyl-coa dehydrogenase deficiency		Association	Human Urine	HMDB	6616873
Refsum's disease		Association	Human Urine	HMDB	6186413
Short chain acyl-coa dehydrogenase deficiency	Increased	Association	Human Urine	HMDB	3571488
Short chain acyl-coa dehydrogenase deficiency	Increased	Association	Human Urine	HMDB	7776094
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	2	Human ; Human mucosa; Human saliva; Human feces; Human sputum; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	2	Human ; Human stool; Human feces; Human saliva; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	7.2				umol/mmol creatinine	Children (1-13 years old)	Male	Ethylmalonic encephalopathy	HMDB	16828325
Human Urine	Detected and Quantified			0.900	16.700	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified			1.100	5.900	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified			11.400	17.300	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified			5.200	62.500	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified			3	9	umol/mmol creatinine	Children (1 - 13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	6616873
Human Urine	Detected and Quantified	1.9		1.3	2.5	umol/mmol creatinine	Adult (>18 years old)	Both	Refsum's disease	HMDB	6186413
Human Urine	Detected and Quantified			22.612	101.754	umol/mmol creatinine	Newborn (0-30 days old)	Female	Short Chain Acyl-Coa Dehydrogenase Deficiency	HMDB	3571488
Human Urine	Detected and Quantified			22.612	101.754	umol/mmol creatinine	Infant (0-1 year old)	Female	Short chain acyl-CoA dehydrogenase deficiency (SCAD)	HMDB	3571488
Human Urine	Detected and Quantified			6	630	umol/mmol creatinine	Infant (0-1 year old)	Both	Short chain acyl-CoA Dehydrogenase deficiency (SCAD)	HMDB	7776094
Human Urine	Detected and Quantified	2				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	2.6				umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	2.7				umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	2.8				umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	4.8				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			2	3	umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	6616873
Human Urine	Detected and Quantified	<2.0				umol/mmol creatinine	Children (1-13 years old)	Male	Normal	HMDB	16828325
Human Urine	Detected and Quantified	<3.392				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	3571488
Human Urine	Detected and Quantified	<3.392				umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	3571488
Human Urine	Detected and Quantified			0	1.9	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	3.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	3.1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	5.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0.53	0.85	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.69	1.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.56	1.12			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9439441
Human Feces	Detected and Quantified	151.384	209.666			nmol/g wet feces	Not Specified	Not Specified	Normal	HMDB	20669995
Human Urine	Detected and Quantified	2.3		0.8	10.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6186413
Human Urine	Detected and Quantified	3.2		0.7	9.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	4.7		1.1	6.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	5	3			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	7776094
Human Urine	Detected and Quantified	5.06	0.99			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	10731506
Human Feces	Detected and Quantified	81.520	46.853			nmol/g wet feces	Not Specified	Not Specified	Normal	HMDB	19573517
Human Urine	Detected and Quantified	25.309	83.321			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.467	5.597			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.065	0.863			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	4.899	3.586			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<3.89				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified	0.900	0.800			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.900	0.700			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	8.04	0.4			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9439441
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022704

KNApSAcK ID

C00052350

Chemspider ID

5323413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Methylsuccinic acid

METLIN ID

Not Available

PubChem Compound

6950476

PDB ID

Not Available

ChEBI ID

91316

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0022-3476(95)70207-5. [PubMed:7776094 ]
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 ]
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. doi: 10.1016/s0026-0495(98)90122-6. [PubMed:9667231 ]
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. doi: 10.1007/s00415-002-0880-4. [PubMed:12382164 ]
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. doi: 10.1016/j.tox.2004.08.023. [PubMed:15596249 ]

Showing metabocard for Methylsuccinic acid (MMDBc0000392)

MOL for #<Metabolite:0x00007fdaf61f7538>

3D MOL for #<Metabolite:0x00007fdaf61f7538>

3D SDF for #<Metabolite:0x00007fdaf61f7538>

3D-SDF for #<Metabolite:0x00007fdaf61f7538>

PDB for #<Metabolite:0x00007fdaf61f7538>

3D PDB for #<Metabolite:0x00007fdaf61f7538>

SMILES for #<Metabolite:0x00007fdaf61f7538>

INCHI for #<Metabolite:0x00007fdaf61f7538>

Structure for #<Metabolite:0x00007fdaf61f7538>

3D Structure for #<Metabolite:0x00007fdaf61f7538>