MiMeDB: Showing metabocard for (S)-malate(2-) (MMDBc0033207)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:39:05 UTC

Update Date

2022-08-31 22:29:48 UTC

Metabolite ID

MMDBc0033207

Metabolite Identification

Common Name

(S)-malate(2-)

Description

Malic acid is the active ingredient in many sour or tart foods. Malic acid is found mostly in unripe fruits. Malic acid has two stereoisomeric forms (L- and D- enantiomers), though only the L- isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is an intermediate in the citric acid cycle. Malic acid produces the green apple taste/aroma for wines.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-Malate	ChEBI
L-Malate	ChEBI
(S)-Malic acid	Generator
L-Malic acid	Generator
(S)-Malic acid(2-)	Generator

Molecular Formula

C₄H₄O₅

Average Mass

132.0716

Monoisotopic Mass

132.005873238

IUPAC Name

(2S)-2-hydroxybutanedioate

Traditional Name

L-malate

CAS Registry Number

Not Available

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)/p-2/t2-/m0/s1

InChI Key

BJEPYKJPYRNKOW-REOHCLBHSA-L

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
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

malate(2-) (CHEBI:15589 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	826 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-1.1	ChemAxon
logS	0.69	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	1	ChemAxon
Polar Surface Area	100.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.55 m³·mol⁻¹	ChemAxon
Polarizability	10.08 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-a781f8077cf9fca7fe06	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4900000000-50ed48c28466de97962f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h90-9400000000-fbf394509fd7fbe4c5ed	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9100000000-123fd0ad32dec4bef6ff	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-61c83d57155eb5a77fb4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-16e60d8dcead278c465f	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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	Data Source	Reference
MMDBr0001248	Fumaric acid	(S)-malate(2-)	fumarate hydratase	VMH; KEGG	16774737 17111171 17111172
MMDBr0001629	(S)-malate(2-)	Oxalacetic acid	malate dehydrogenase 1, NAD (soluble)	VMH; KEGG	30371894
MMDBr0005498	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH	30371894
MMDBr0007198	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH	30371894
MMDBr0007201	(S)-malate(2-)	Menaquinol 8	Not Available	VMH	30371894
MMDBr0007412	Fumaric acid	(S)-malate(2-)	Not Available	VMH; KEGG	30371894
MMDBr0007837	(S)-malate(2-)	Glyoxylic acid	Not Available	VMH	30371894
MMDBr0007900	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0008525	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	9	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	399	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle ; Human saliva; Human mucosa; Human unknown; Human urine; Human supragingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	568	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool; Chicken ; River trout ; Sheep ; Human subgingival plaque; Cattle ; Rat ; Turkey ; Dog ; American dog tick ; Human urine	Metabolic reconstruction
Bacteria	Actinobacteria	165	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	121	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	7	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Archaea	Crenarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	7	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	19		Metabolic reconstruction
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Deinococcus-thermus	7
Bacteria	Cyanobacteria	9
Bacteria	nah	1
Eukaryota/Fungi	Mucoromycota	1
Eukaryota/Fungi	Chytridiomycota	1
Bacteria	Chloroflexi	10
Bacteria	Chlorobi	12
Bacteria	Aquificae	3
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea/Archaea	nah	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

MAL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459792

PDB ID

Not Available

ChEBI ID

15589

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Palmieri F: The mitochondrial transporter family (SLC25): physiological and pathological implications. Pflugers Arch. 2004 Feb;447(5):689-709. doi: 10.1007/s00424-003-1099-7. Epub 2003 Nov 4. [PubMed:14598172 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (S)-malate(2-) (MMDBc0033207)

MOL for #<Metabolite:0x00007fece9a5aa68>

3D MOL for #<Metabolite:0x00007fece9a5aa68>

3D SDF for #<Metabolite:0x00007fece9a5aa68>

3D-SDF for #<Metabolite:0x00007fece9a5aa68>

PDB for #<Metabolite:0x00007fece9a5aa68>

3D PDB for #<Metabolite:0x00007fece9a5aa68>

SMILES for #<Metabolite:0x00007fece9a5aa68>

INCHI for #<Metabolite:0x00007fece9a5aa68>

Structure for #<Metabolite:0x00007fece9a5aa68>

3D Structure for #<Metabolite:0x00007fece9a5aa68>