Cannabis Compound Database: Showing Compound Card for Malic acid (CDB006173)

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Record Information

Version

1.0

Created at

2020-03-18 23:22:30 UTC

Updated at

2022-12-13 23:36:27 UTC

CannabisDB ID

CDB006173

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Malic acid

Description

Malic acid is odorless and 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. Indeed, malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. 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. Malic acid is an extremely weak acidic compound (based on its pKa). Malic acid exists in all living organisms, ranging from bacteria to humans. 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 is abundant in many fruits and is the main acid found in apricots, blackberries, blueberries, cherries, mirabelles, peaches, pears, plums, and quince. Malic acid is also present in grapes and in most wines with concentrations as high as 5 g/l. The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor. It is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips. Therefore malic acid is a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-D-Malic acid	ChEBI
(R)-2-Hydroxybutanedioic acid	ChEBI
2-HYDROXY-succinIC ACID	ChEBI
D-Malate	Kegg
(+)-D-Malate	Generator
(R)-2-Hydroxybutanedioate	Generator
2-HYDROXY-succinate	Generator
(R)-Malate	HMDB
(R)-Hydroxybutanedioic acid	HMDB
D-(+)-Malic acid	HMDB
D-Hydroxybutanedioic acid	HMDB
Hydroxy-(R)-butanedioic acid	HMDB
R-Malic acid	HMDB
D-Malic acid	ChEBI

Chemical Formula

C₄H₆O₅

Average Molecular Weight

134.09

Monoisotopic Molecular Weight

134.0215

IUPAC Name

(2R)-2-hydroxybutanedioic acid

Traditional Name

.+-.-malic acid

CAS Registry Number

636-61-3

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-/m1/s1

InChI Key

BJEPYKJPYRNKOW-UWTATZPHSA-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:30796 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	101 °C	Not Available
Boiling Point	306.4 °C	Wikipedia
Water Solubility	364 mg/mL at 20 °C	Not Available
logP	-1.26	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Malic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0930000000-53a536e3bc82b8e91612	Spectrum
GC-MS	Malic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9610000000-883e07f52319a029b9f9	Spectrum
GC-MS	Malic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0930000000-53a536e3bc82b8e91612	Spectrum
GC-MS	Malic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9610000000-883e07f52319a029b9f9	Spectrum
Predicted GC-MS	Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9100000000-add08efe51cfe6d9243c	Spectrum
Predicted GC-MS	Malic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02j9-7191000000-b78c78194b39deee0ca4	Spectrum
Predicted GC-MS	Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0159-3900000000-b601107a03ca7060bc56	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-7900000000-7e16d13cd13953520b72	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-ed4a8a4776b51e62327c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-22c9ebc50090b4cd6671	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-6900000000-3b7d14a7ed7bb42627e4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bj-9300000000-20f68e610aeba32d1947	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-044292489a383c81ae1d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00m0-8900000000-9da4062d3c439ed2f7eb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ri-9200000000-c4d019ab4961e5b1a1ae	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-bc073c2d0e1a2f8a82e3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00y0-9400000000-b346287170f4b47937d9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00du-9000000000-94fcc5032bed94eae77e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-43c40f8a7715a996c55b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ri-9400000000-a20ca040dba0bb25ae2b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0095-9000000000-90064952bc6def150ecc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4dd1a07ea5d3aab2c6ea	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Polycystic kidney disease 2-like 1 protein	PKD2L1	10q24	Q9P0L9	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Polycystic kidney disease 2-like 1 protein	PKD2L1	10q24	Q9P0L9	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.716 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.288 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.583 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.216 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.921 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.475 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0031518

DrugBank ID

DB03499

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008115

KNApSAcK ID

Not Available

Chemspider ID

83793

KEGG Compound ID

C00497

BioCyc ID

CPD-660

BiGG ID

Not Available

Wikipedia Link

Malic_acid

METLIN ID

Not Available

PubChem Compound

92824

PDB ID

DMR

ChEBI ID

30796

References

General References

Li D, Li W, Wang Q, Yang Z, Hou Z: Concise synthesis of Cannabisin G. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5095-8. doi: 10.1016/j.bmcl.2010.07.028. Epub 2010 Jul 11. [PubMed:20667725 ]

Enzymes

Enzyme Details

1. Polycystic kidney disease 2-like 1 protein

General function:: Involved in calcium ion binding
Specific function:: May function as a subunit of an ion channel and act as a transducer of calcium-mediated signaling
Gene Name:: PKD2L1
Uniprot ID:: Q9P0L9
Molecular weight:: 91981.2

Showing Compound Card for Malic acid (CDB006173)

Structure for CDB006173 (Malic acid)

Enzymes