ChemFOnt: Showing chemical card for Malic acid (CFc000000101)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:24 UTC

Chemfont ID

CFc000000101

Molecule Identification

Common Name

Malic acid

Definition

2250

Structure

MOL SDF PDB SMILES InChI

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 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000156)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Cellular Cytoplasm (PMID: 8579834)
Cerebrospinal Fluid (CSF) (PMID: 8412012)
Saliva (PMID: 22308371)
Cerebrospinal fluid (HMDB: HMDB0000156)

Organ

Prostate (HMDB: HMDB0000156)
Placenta (HMDB: HMDB0000156)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 19573517)
Sweat (PMID: 26755145)

Cellular substructure

Cytoplasm (HMDB: HMDB0000156)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000156)

Source

Exogenous

Exogenous (HMDB: HMDB0000156)

Food

Food (HMDB: HMDB0000156)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Quince (FooDB: FOOD00069)

Fig (FooDB: FOOD00081)

Citrus

Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Soy

Soy bean (FooDB: FOOD00085)

Vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Spinach (FooDB: FOOD00178)

Root vegetable

Tuber

Potato (FooDB: FOOD00175)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Fruit vegetable

Mexican groundcherry (FooDB: FOOD00491)
Garden tomato (var.) (FooDB: FOOD00173)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Ginkgo nuts (FooDB: FOOD00367)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Bean

Broad bean (FooDB: FOOD00197)

Other pulse

White lupine (FooDB: FOOD00403)

Tea

Nut

Common walnut (FooDB: FOOD00094)

Endogenous

Endogenous (HMDB: HMDB0000156)

Plant

Animal

Animal (HMDB: HMDB0000156)

Fungi

Aspergillus (HMDB: HMDB0000156)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Glycogenosis, Type IB (HMDB: HMDB0000156)
The Oncogenic Action of Succinate (PathBank: SMP0002292)
Glutaminolysis and Cancer (PathBank: SMP0108773)
Leigh Syndrome (PathBank: SMP0120726)
Pyruvate Dehydrogenase Deficiency (E3) (PathBank: SMP0120833)
Pyruvate Dehydrogenase Deficiency (E2) (PathBank: SMP0120834)
The Oncogenic Action of 2-Hydroxyglutarate (PathBank: SMP0002291)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0120533)
Congenital Lactic Acidosis (PathBank: SMP0120610)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
2-Ketoglutarate Dehydrogenase Complex Deficiency (PathBank: SMP0120832)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0120531)
Fumarase Deficiency (PathBank: SMP0120611)
Mitochondrial Complex II Deficiency (PathBank: SMP0120831)
The Oncogenic Action of Fumarate (PathBank: SMP0002295)
The Oncogenic Action of L-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002358)
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002359)

Metabolic pathway

Pyruvate Metabolism (PathBank: SMP0002355)
TCA Cycle (PathBank: SMP0002414)
Citric Acid Cycle (PathBank: SMP0063477)
Transfer of Acetyl Groups into Mitochondria (PathBank: SMP0087254)
Warburg Effect (PathBank: SMP0087270)
Secondary Metabolites: Glyoxylate Cycle (PathBank: SMP0121326)
TCA Cycle (Ubiquinol-4) (PathBank: SMP0121339)
TCA Cycle (Ubiquinol-5) (PathBank: SMP0121340)
TCA Cycle (Ubiquinol-7) (PathBank: SMP0121342)
TCA Cycle (Ubiquinol-8) (PathBank: SMP0121343)
Gluconeogenesis (HMDB: HMDB0000156)
TCA Cycle (Ubiquinol-10) (PathBank: SMP0121345)
Gluconeogenesis from L-Malic Acid (PathBank: SMP0002413)
Glycolate and Glyoxylate Degradation (PathBank: SMP0121295)
TCA Cycle (Ubiquinol-6) (PathBank: SMP0121341)
TCA Cycle (Ubiquinol-0) (PathBank: SMP0122219)
Aspartate Metabolism (PathBank: SMP0002302)
TCA Cycle (PathBank: SMP0002304)
Aspartate Metabolism (PathBank: SMP0002422)
Inner Membrane Transport (PathBank: SMP0121270)
TCA Cycle (Ubiquinol-2) (PathBank: SMP0121337)
TCA Cycle (Ubiquinol-9) (PathBank: SMP0121344)
TCA Cycle (Ubiquinol-3) (PathBank: SMP0121338)
Glycolate and Glyoxylate Degradation II (PathBank: SMP0122218)
Gluconeogenesis (HMDB: HMDB0000156)
Malate-Aspartate Shuttle (HMDB: HMDB0000156)
Gluconeogenesis from L-Malic Acid (PathBank: SMP0000839)
Glyoxylate Cycle (PathBank: SMP0002336)
Citrate Cycle (PathBank: SMP0121182)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000156)

Antineoplastic agent

Antitumor (HMDB: HMDB0000156)

Digestive system agent

Gastrointestinal agent

Laxative (HMDB: HMDB0000156)

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000075)
Eosinophilic esophagitis (MarkerDB: MDB00000075)
Lewy Body Dementia (MarkerDB: MDB00000075)
Anoxia (MarkerDB: MDB00000075)

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000156)
Antioxidant (HMDB: HMDB0000156)

Agriculture

Pesticide (HMDB: HMDB0000156)

Biological role

Anti atherosclerotic (HMDB: HMDB0000156)
Anti bacterial (HMDB: HMDB0000156)
Anti fibromyalgic (HMDB: HMDB0000156)
Anti seborrheic (HMDB: HMDB0000156)
Anti septic (HMDB: HMDB0000156)
Anti tubercular (HMDB: HMDB0000156)
Bacteristat (HMDB: HMDB0000156)
Bruchiphobe (HMDB: HMDB0000156)
Hemopoietic (HMDB: HMDB0000156)
Mycobactericide (HMDB: HMDB0000156)
Sialogogue (HMDB: HMDB0000156)

Physical Properties

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

External Links

HMDB ID

HMDB0000156

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

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.

Showing chemical card for Malic acid (CFc000000101)

MOL for CFc000000101 (Malic acid)

3D MOL for CFc000000101 (Malic acid)

3D SDF for CFc000000101 (Malic acid)

3D-SDF for CFc000000101 (Malic acid)

PDB for CFc000000101 (Malic acid)

3D PDB for CFc000000101 (Malic acid)

SMILES for CFc000000101 (Malic acid)

INCHI for CFc000000101 (Malic acid)

Structure for CFc000000101 (Malic acid)

3D Structure for CFc000000101 (Malic acid)