Cannabis Compound Database: Showing Compound Card for Fumaric acid (CDB004809)

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Record Information

Version

1.0

Created at

2020-04-17 18:38:59 UTC

Updated at

2022-12-13 23:36:28 UTC

CannabisDB ID

CDB004809

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Fumaric acid

Description

Fumaric acid, also known as E297 or fumarsaeure, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans. Within humans, fumaric acid participates in a number of enzymatic reactions. In particular, fumaric acid can be biosynthesized from L-malic acid; which is catalyzed by the enzyme fumarate hydratase, mitochondrial. In addition, fumaric acid can be biosynthesized from succinic acid through the action of the enzyme mutant succinate dehydrogenase. A butenedioic acid in which the C=C double bond has E geometry. In humans, fumaric acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Fumaric acid is an odorless and sour tasting compound. Outside of the human body, Fumaric acid is found, on average, in the highest concentration within a few different foods, such as sweet cherries, star fruits, and milk (cow) and in a lower concentration in grape wines. Fumaric acid has also been detected, but not quantified in, several different foods, such as cow milks, apples, fishes, garden rhubarbs, and common sages. This could make fumaric acid a potential biomarker for the consumption of these foods. Fumaric acid is a potentially toxic compound. Fumaric acid, with regard to humans, has been found to be associated with several diseases such as rheumatoid arthritis, eosinophilic esophagitis, and lung cancer; fumaric acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and fumarase deficiency. Fumaric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-2-Butenedioic acid	ChEBI
(e)-2-Butenedioic acid	ChEBI
e297	ChEBI
Fumarsaeure	ChEBI
trans-1,2-Ethylenedicarboxylic acid	ChEBI
trans-But-2-enedioic acid	ChEBI
trans-Butenedioic acid	ChEBI
(2E)-2-Butenedioate	Generator
(e)-2-Butenedioate	Generator
trans-1,2-Ethylenedicarboxylate	Generator
trans-But-2-enedioate	Generator
trans-Butenedioate	Generator
Fumarate	Generator
(2E)-But-2-enedioate	HMDB
(2E)-But-2-enedioic acid	HMDB
2-(e)-Butenedioate	HMDB
2-(e)-Butenedioic acid	HMDB
Allomaleate	HMDB
Allomaleic acid	HMDB
Boletate	HMDB
Boletic acid	HMDB
FC 33	HMDB
Lichenate	HMDB
Lichenic acid	HMDB
trans-2-Butenedioate	HMDB
trans-2-Butenedioic acid	HMDB
Furamag	HMDB
Mafusol	HMDB
Fumaric acid	HMDB

Chemical Formula

C₄H₄O₄

Average Molecular Weight

116.07

Monoisotopic Molecular Weight

116.011

IUPAC Name

(2E)-but-2-enedioic acid

Traditional Name

fumaric acid

CAS Registry Number

110-17-8

SMILES

OC(=O)\C=C\C(O)=O

InChI Identifier

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

InChI Key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butenedioic acid (CHEBI:18012 )

Ontology

Physiological effect

Health effect:

Observation:

Skin irritation

Health condition:

Nervous system disorders:

Seizure

Respiratory, thoracic and mediastinal disorders:

Cough

Gastrointestinal disorders:

Cancer:

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Fungi:

Aspergillus

Plant:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Biofluid and excreta:

Cell and elements:

Extracellular

Air pollutant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	549 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7 mg/mL	Not Available
logP	0.46	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.21	ALOGPS
logP	-0.041	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	24.61 m³·mol⁻¹	ChemAxon
Polarizability	9.35 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	2014-09-20	View Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-9100000000-2cf649749b42cc0c610c	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0007-0890000000-b1c35cd55deb81254f66	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0940000000-177fdb9168659029ffaa	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	Spectrum
Predicted GC-MS	Fumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TBDMS_2_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, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-04b277f233e1bd56c9af	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4900000000-99764eff7d7cb7bfaee3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-453b921a0aaf64cfd558	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9000000000-cd7e7026d13bb5fe844b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-9000000000-383c22a29e2769626c47	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ir3-9000000000-3013847e2e0f9bf18d29	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-9cc4f29b523ed34dc0b6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00di-9000000000-d9885a6093f38dd8b9fa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-9000000000-46fdee94b5a787f1b81f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03k9-8900000000-3ff0fb725ec9dffc3688	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014m-9000000000-394fd8f1b59c7befec9d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-3d34cd791255c022876a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-55a5c43ec34fdd2cb0a4	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9000000000-7c9639a65d534cd8ff97	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-9000000000-c5eb63dc643f72e91ede	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phenylalanine and Tyrosine Metabolism
Arginine and Proline Metabolism
Aspartate Metabolism
Urea Cycle
Mitochondrial Electron Transport Chain

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Succinate dehydrogenase cytochrome b560 subunit, mitochondrial	SDHC	1q23.3	Q99643	details
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	SDHA	5p15	P31040	details
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial	SDHD	11q23	O14521	details
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	SDHB	1p36.1-p35	P21912	details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details
Adenylosuccinate lyase	ADSL	22q13.2	P30566	details
Argininosuccinate lyase	ASL	7q11.21	P04424	details
Fumarylacetoacetase	FAH	15q25.1	P16930	details
Fumarate hydratase, mitochondrial	FH	1q42.1	P07954	details
Fumarate hydratase	FH	1q42.1	B1ANK7	details
Acylpyruvase FAHD1, mitochondrial	FAHD1	16p13.3	Q6P587	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Succinate dehydrogenase cytochrome b560 subunit, mitochondrial	SDHC	1q23.3	Q99643	details
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial	SDHD	11q23	O14521	details
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	SDHB	1p36.1-p35	P21912	details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details
Fumarylacetoacetase	FAH	15q25.1	P16930	details
NAD-dependent malic enzyme, mitochondrial	ME2	18q21	P23368	details
Acylpyruvase FAHD1, mitochondrial	FAHD1	16p13.3	Q6P587	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0222 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0121 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0209 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00696 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0745 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0142 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000134

DrugBank ID

DB01677

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18012

References

General References

Not Available

Only showing the first 10 proteins. There are 18 proteins in total.

Show All

Enzymes

Enzyme Details

1. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial

General function:: Involved in succinate dehydrogenase activity
Specific function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHC
Uniprot ID:: Q99643
Molecular weight:: 16650.185

Enzyme Details

2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

General function:: Involved in electron carrier activity
Specific function:: Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:: SDHA
Uniprot ID:: P31040
Molecular weight:: 72690.975

Enzyme Details

3. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial

General function:: Involved in iron ion binding
Specific function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
Gene Name:: SDHD
Uniprot ID:: O14521
Molecular weight:: 17042.82

Enzyme Details

4. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial

General function:: Involved in electron carrier activity
Specific function:: Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHB
Uniprot ID:: P21912
Molecular weight:: 31629.365

Enzyme Details

5. Dopamine beta-hydroxylase