AFCDB: L-Malic acid (FDB001044)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:49 UTC

Update date

2019-11-26 02:55:50 UTC

Primary ID

FDB001044

Secondary Accession Numbers

FDB030170

Chemical Information

FooDB Name

L-Malic acid

Description

L-Malic acid, also known as malate or L-apple acid, 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. L-Malic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Malic acid exists in all eukaryotes, ranging from yeast to humans. L-Malic acid, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, colorectal cancer, eosinophilic esophagitis, and missing teeth; L-malic acid has also been linked to the inborn metabolic disorder 2-ketoglutarate dehydrogenase complex deficiency.

CAS Number

97-67-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C4H6O5

IUPAC name

(2S)-2-hydroxybutanedioic acid

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

Isomeric SMILES

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

Average Molecular Weight

134.0874

Monoisotopic Molecular Weight

134.021523302

Classification

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

Anoxia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Prostate

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 35.83%; H 4.51%; O 59.66%	DFC
Melting Point	Mp 104-105° (100°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa2 5.1	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -28.7 (c, 5.5 in Py) (>99.8% ee)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0076-9000000000-ad60ea592282d09e4bd8	2020-02-03	View Spectrum
GC-MS	L-Malic acid, 3 TMS, GC-MS Spectrum	splash10-000t-0940000000-142d6f5fc2efbf0d5109	Spectrum
GC-MS	L-Malic acid, 3 TMS, GC-MS Spectrum	splash10-0002-0920000000-505483ce10ee3c4c9d20	Spectrum
GC-MS	L-Malic acid, 3 TMS, GC-MS Spectrum	splash10-00di-9710000000-8f263d045d715ae9fe2b	Spectrum
GC-MS	L-Malic acid, non-derivatized, GC-MS Spectrum	splash10-000t-0940000000-142d6f5fc2efbf0d5109	Spectrum
GC-MS	L-Malic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0920000000-505483ce10ee3c4c9d20	Spectrum
GC-MS	L-Malic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9710000000-8f263d045d715ae9fe2b	Spectrum
GC-MS	L-Malic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-fadd80af55894555ea72	Spectrum
Predicted GC-MS	L-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9100000000-aba7652c885a434930ef	Spectrum
Predicted GC-MS	L-Malic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02j9-7191000000-b78c78194b39deee0ca4	Spectrum
Predicted GC-MS	L-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Malic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

193317

ChEMBL ID

Not Available

KEGG Compound ID

C00149

Pubchem Compound ID

222656

Pubchem Substance ID

Not Available

ChEBI ID

15589

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00156

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1030861

SuperScent ID

Not Available

Wikipedia ID

Malic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Fumarate hydratase, mitochondrial	FH	P07954

Pathways

Name	SMPDB Link	KEGG Link
Citric Acid Cycle	SMP00057	map00020
Pyruvate Metabolism	SMP00060	map00620
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Malic acid (FDB001044)

Structure for FDB001044 (L-Malic acid)