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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:01 UTC

HMDB ID

HMDB0000156

Secondary Accession Numbers

HMDB0000744
HMDB00156
HMDB00744

Metabolite Identification

Common Name

Malic acid

Description

Malic acid (CAS: 6915-15-7) is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness (Wikipedia ). In its ionized form, malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats, it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production. Malic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-L-Malic acid	ChEBI
(S)-(-)-Hydroxysuccinic acid	ChEBI
L-2-Hydroxybutanedioic acid	ChEBI
L-Apple acid	ChEBI
Malate	ChEBI
Malic acid	ChEBI
S-2-Hydroxybutanedioic acid	ChEBI
L-Malate	Kegg
(-)-L-Malate	Generator
(S)-(-)-Hydroxysuccinate	Generator
L-2-Hydroxybutanedioate	Generator
S-2-Hydroxybutanedioate	Generator
(-)-(S)-Malate	HMDB
(-)-(S)-Malic acid	HMDB
(-)-Hydroxysuccinate	HMDB
(-)-Hydroxysuccinic acid	HMDB
(-)-Malic acid	HMDB
(2S)-2-Hydroxybutanedioate	HMDB
(2S)-2-Hydroxybutanedioic acid	HMDB
(S)-Hydroxy-butanedioate	HMDB
(S)-Hydroxy-butanedioic acid	HMDB
(S)-Hydroxybutanedioate	HMDB
(S)-Hydroxybutanedioic acid	HMDB
(S)-Malic acid	HMDB
Apple acid	HMDB
L-(-)-Malic acid	HMDB
L-Hydroxybutanedioate	HMDB
L-Hydroxybutanedioic acid	HMDB
L-Hydroxysuccinate	HMDB
L-Hydroxysuccinic acid	HMDB
S-(-)-Malate	HMDB
S-(-)-Malic acid	HMDB
(S)-Malate	HMDB
L-Malic acid	ChEBI
(2S)-2-Hydroxysuccinic acid	HMDB
(2S)-Malic acid	HMDB
(S)-2-Hydroxysuccinic acid	HMDB
2-Hydroxybutanedioic acid	HMDB
2-Hydroxyethane-1,2-dicarboxylic acid	HMDB
2-Hydroxysuccinic acid	HMDB
Deoxytetraric acid	HMDB
Hydroxybutanedioic acid	HMDB
Hydroxysuccinic acid	HMDB
Monohydroxybutanedioic acid	HMDB
alpha-Hydroxysuccinic acid	HMDB
α-Hydroxysuccinic acid	HMDB

Chemical Formula

C₄H₆O₅

Average Molecular Weight

134.0874

Monoisotopic Molecular Weight

134.021523302

IUPAC Name

(2S)-2-hydroxybutanedioic acid

Traditional Name

(-)-malic acid

CAS Registry Number

97-67-6

SMILES

O[C@@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

InChI Key

BJEPYKJPYRNKOW-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

malic acid (CHEBI:30797 )

Ontology

Exogenous (FooDB: )

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	107 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	116.3	30932474
[M-H]-	Not Available	117.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001763

Predicted Molecular Properties

Property	Value	Source
Water Solubility	218 g/L	ALOGPS
logP	-0.87	ALOGPS
logP	-1.1	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.88 m³·mol⁻¹	ChemAxon
Polarizability	10.93 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.159	31661259
DarkChem	[M-H]-	121.812	31661259
AllCCS	[M+H]+	131.873	32859911
AllCCS	[M-H]-	122.689	32859911
DeepCCS	[M+H]+	122.754	30932474
DeepCCS	[M-H]-	118.888	30932474
DeepCCS	[M-2H]-	156.466	30932474
DeepCCS	[M+Na]+	131.713	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	122.7	32859911
AllCCS	[M+Na-2H]-	125.3	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Malic acid	O[C@@H](CC(O)=O)C(O)=O	2199.2	Standard polar	33892256
Malic acid	O[C@@H](CC(O)=O)C(O)=O	1008.0	Standard non polar	33892256
Malic acid	O[C@@H](CC(O)=O)C(O)=O	1328.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Malic acid,1TMS,isomer #1	C[Si](C)(C)O[C@@H](CC(=O)O)C(=O)O	1317.5	Semi standard non polar	33892256
Malic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C[C@H](O)C(=O)O	1311.4	Semi standard non polar	33892256
Malic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](O)CC(=O)O	1279.0	Semi standard non polar	33892256
Malic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C[C@H](O[Si](C)(C)C)C(=O)O	1404.0	Semi standard non polar	33892256
Malic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC(=O)O)O[Si](C)(C)C	1376.6	Semi standard non polar	33892256
Malic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C[C@H](O)C(=O)O[Si](C)(C)C	1382.5	Semi standard non polar	33892256
Malic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1498.5	Semi standard non polar	33892256
Malic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](CC(=O)O)C(=O)O	1572.3	Semi standard non polar	33892256
Malic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O)C(=O)O	1571.3	Semi standard non polar	33892256
Malic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)CC(=O)O	1555.1	Semi standard non polar	33892256
Malic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1851.7	Semi standard non polar	33892256
Malic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	1836.9	Semi standard non polar	33892256
Malic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1825.4	Semi standard non polar	33892256
Malic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2116.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000t-0940000000-142d6f5fc2efbf0d5109	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0002-0920000000-505483ce10ee3c4c9d20	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9710000000-8f263d045d715ae9fe2b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Non-derivatized)	splash10-000t-0940000000-142d6f5fc2efbf0d5109	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-505483ce10ee3c4c9d20	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9710000000-8f263d045d715ae9fe2b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Malic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-fadd80af55894555ea72	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-aba7652c885a434930ef	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (3 TMS) - 70eV, Positive	splash10-02j9-7191000000-b78c78194b39deee0ca4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0076-9000000000-ad60ea592282d09e4bd8	2020-02-03	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-9300000000-acd7d0159b8bb70b80fd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0096-9000000000-7359292556d9d393d8f4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0097-9000000000-a111335688b3219c1fc1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00lr-0942120000-9504700a82dcf5dc3adb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0900000000-45e58d8a75d957cc5c41	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-03di-0900000000-4ec56105367de7bf0027	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-001i-0900000000-1decf12f117200e0f28d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-03di-4900000000-86fd329658581c81c0ec	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-00di-9100000000-82ffef2aa053f77cdbc5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-00di-9000000000-424bd54bc81a9db65a55	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-9000000000-a916941735427ee3c48d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-1decf12f117200e0f28d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ , negative-QTOF	splash10-03di-4900000000-86fd329658581c81c0ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ , negative-QTOF	splash10-00di-9100000000-82ffef2aa053f77cdbc5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-424bd54bc81a9db65a55	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-a916941735427ee3c48d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid LC-ESI-ITFT , negative-QTOF	splash10-03di-0900000000-afdfdad3edeeb90cb3e4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid , negative-QTOF	splash10-01b9-4900000000-01b3a756de8f5a3ae6de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malic acid 35V, Negative-QTOF	splash10-01b9-4900000000-5fc3f0befc374a6fcdd6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 10V, Positive-QTOF	splash10-00kr-7900000000-2a07c36db6acea9015af	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 20V, Positive-QTOF	splash10-00rj-9200000000-316c7803efd1dfb76523	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 40V, Positive-QTOF	splash10-00dl-9000000000-a442bcaaacb6f4eec14d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 10V, Negative-QTOF	splash10-001r-9800000000-03bfaee5de56f72ed927	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 20V, Negative-QTOF	splash10-0079-9200000000-26a075efe73adc63a189	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malic acid 40V, Negative-QTOF	splash10-059f-9000000000-a3281a79477ac14e2eae	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Malate-Aspartate Shuttle		Not Available
Citric Acid Cycle
Gluconeogenesis
Pyruvate metabolism	Not Available
Transfer of Acetyl Groups into Mitochondria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	12.0 (0.0-21.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	3.2 +/- 0.9 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Cellular Cytoplasm	Detected and Quantified	3200 (2800-3600) uM	Adult (>18 years old)	Both	Normal	8579834	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3 uM	Children (1-13 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.0 +/- 3.0 uM	Adult (>18 years old)	Both	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected and Quantified	22.448 +/- 19.987 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected and Quantified	542.929 +/- 378.857 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Saliva	Detected and Quantified	5.22 +/- 3.49 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	6.35 +/- 3.56 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	1.87 +/- 1.06 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	6.45 +/- 2.84 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	3.79 +/- 1.80 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	6.45 +/- 2.09 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	4.15 +/- 6.21 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	4.15 +/- 6.21 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	20.45 +/- 10.87 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	4.53 +/- 2.22 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	18.669 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0-1.1 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Great Plains Labo...	details
Urine	Detected and Quantified	<8 umol/mmol creatinine	Not Specified	Not Specified	Normal	1640293	details
Urine	Detected and Quantified	0-0.1 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0-0.7 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-1.1 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-1.8 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0.57-0.81 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.63 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	2.0 (0.7-5.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.41-0.65 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.46 +/- 0.79 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected and Quantified	64.79 (32.94-109.83) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	116.959 +/- 45.313 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	36.1(12.4-121.6) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	38.9 (25.5-93.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	9.0 (2.2-19.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	8.3 (2.8-30.1) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Cellular Cytoplasm	Detected and Quantified	480 (470-490) uM	Adult (>18 years old)	Both	Anoxia	8579834	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected and Quantified	5.36 +/- 2.50 uM	Adult (>18 years old)	Both	Temporomandibular joint disorder (TMD)	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected and Quantified	22.27 +/- 14.67 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	18.70 +/- 15.26 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	24.13 +/- 19.54 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Sweat	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	screen-positive CF	Adriana Nori...	details
Urine	Detected and Quantified	110 umol/mmol creatinine	Newborn (0-30 days old)	Female	Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome	17994565	details
Urine	Detected and Quantified	33.616 +/- 24.099 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	7-194 umol/mmol creatinine	Infant (0-1 year old)	Male	2-Ketoglutarate dehydrogenase complex deficiency	1640293	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected and Quantified	65.119 +/- 40.319 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	187.187 +/- 183.405 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] 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 ] 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 ] 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 ]
Schizophrenia
Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Anoxia
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Temporomandibular joint disorder
(). Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles. . .
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Cystic fibrosis
Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
2-Ketoglutarate dehydrogenase complex deficiency
Bonnefont JP, Chretien D, Rustin P, Robinson B, Vassault A, Aupetit J, Charpentier C, Rabier D, Saudubray JM, Munnich A: Alpha-ketoglutarate dehydrogenase deficiency presenting as congenital lactic acidosis. J Pediatr. 1992 Aug;121(2):255-8. [PubMed:1640293 ]
Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome
James AW, Miranda SG, Culver K, Hall BD, Golabi M: DOOR syndrome: clinical report, literature review and discussion of natural history. Am J Med Genet A. 2007 Dec 1;143A(23):2821-31. doi: 10.1002/ajmg.a.32054. [PubMed:17994565 ]

Associated OMIM IDs

114500 (Colorectal cancer)
181500 (Schizophrenia)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)
219700 (Cystic fibrosis)
610247 (Eosinophilic esophagitis)
203740 (2-Ketoglutarate dehydrogenase complex deficiency)
220500 (Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

222656

PDB ID

Not Available

ChEBI ID

30797

Food Biomarker Ontology

Not Available

VMH ID

MAL_L

MarkerDB ID

MDB00000075

Good Scents ID

Not Available

References

Synthesis Reference

McKenzie, Alex.; Plenderleith, H. J.; Walker, Nellie. Optical activation of racemic acid by d-malic acid. Journal of the Chemical Society, Transactions (1923), 123 2875-80.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
Fang TJ, Dalmasso JP: Antimicrobial activity of sulfur dioxide to certain lactic acid bacteria isolated from wines. Zhonghua Min Guo Wei Sheng Wu Ji Mian Yi Xue Za Zhi. 1993 Aug;26(3):116-31. [PubMed:7982367 ]
Splittstoesser DF, McLellan MR, Churey JJ: Heat resistance of Escherichia coli O157:H7 in apple juice. J Food Prot. 1996 Mar;59(3):226-9. [PubMed:10463437 ]
Denayrolles M, Aigle M, Lonvaud-Funel A: Cloning and sequence analysis of the gene encoding Lactococcus lactis malolactic enzyme: relationships with malic enzymes. FEMS Microbiol Lett. 1994 Feb 1;116(1):79-86. [PubMed:8132158 ]
Hem SL: Elimination of aluminum adjuvants. Vaccine. 2002 May 31;20 Suppl 3:S40-3. [PubMed:12184363 ]
Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
Anneroth G, Nordenram G, Bengtsson S: Effect of saliva stimulants (Hybrin and malic acid) on cervical root surfaces in vitro. Scand J Dent Res. 1980 Jun;88(3):214-8. [PubMed:6932087 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. NADP-dependent malic enzyme

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ME1
Uniprot ID:: P48163
Molecular weight:: 64149.075

Reactions

Malic acid + NADP → Pyruvic acid + CO(2) + NADPH	details
Malic acid + NADP → Pyruvic acid + Carbon dioxide + NADPH + Hydrogen Ion	details

Enzyme Details

2. Malate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: MDH2
Uniprot ID:: P40926
Molecular weight:: 35502.935

Reactions

Malic acid + NAD → Oxalacetic acid + NADH	details
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

3. NADP-dependent malic enzyme, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ME3
Uniprot ID:: Q16798
Molecular weight:: 67067.875

Reactions

Malic acid + NADP → Pyruvic acid + CO(2) + NADPH	details
Malic acid + NADP → Pyruvic acid + Carbon dioxide + NADPH + Hydrogen Ion	details

Enzyme Details

4. Malate dehydrogenase, cytoplasmic

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: MDH1
Uniprot ID:: P40925
Molecular weight:: 38627.255

Reactions

Malic acid + NAD → Oxalacetic acid + NADH	details
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

5. Fumarate hydratase, mitochondrial

General function:: Involved in fumarate hydratase activity
Specific function:: Also acts as a tumor suppressor.
Gene Name:: FH
Uniprot ID:: P07954
Molecular weight:: 54636.585

Reactions

Malic acid → Fumaric acid + Water	details

Enzyme Details

6. NAD-dependent malic enzyme, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ME2
Uniprot ID:: P23368
Molecular weight:: 53585.73

Reactions

Malic acid + NAD → Pyruvic acid + CO(2) + NADH	details
Malic acid + NAD → Pyruvic acid + Carbon dioxide + NADH + Hydrogen Ion	details

Enzyme Details

7. Fumarate hydratase

General function:: Involved in fumarate hydratase activity
Specific function:: Not Available
Gene Name:: FH
Uniprot ID:: B1ANK7
Molecular weight:: 54636.6

Showing metabocard for Malic acid (HMDB0000156)

MOL for HMDB0000156 (Malic acid)

3D MOL for HMDB0000156 (Malic acid)

3D SDF for HMDB0000156 (Malic acid)

3D-SDF for HMDB0000156 (Malic acid)

PDB for HMDB0000156 (Malic acid)

3D PDB for HMDB0000156 (Malic acid)

SMILES for HMDB0000156 (Malic acid)

INCHI for HMDB0000156 (Malic acid)

Structure for HMDB0000156 (Malic acid)

3D Structure for HMDB0000156 (Malic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions