Human Metabolome Database: Showing metabocard for Gingerol (HMDB0005783)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2007-01-22 09:25:58 UTC

Update Date

2020-02-26 21:26:04 UTC

HMDB ID

HMDB0005783

Secondary Accession Numbers

HMDB05783

Metabolite Identification

Common Name

Gingerol

Description

Gingerol, also known as 6G [6]-gingerol or (6)-gingerol, belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one. When ginger is dried or mildly heated, gingerol undergoes a dehydration reaction forming shogaols, which are about twice as pungent as gingerol. Gingerol is an extremely weak basic (essentially neutral) compound (based on its pKa). Gingerol is a pungent. Outside of the human body, gingerol is found, on average, in the highest concentration in gingers. gingerol has also been detected, but not quantified in, several different foods, such as pepper (spice), cumins, sweet bay, nutmegs, and caraway. This could make gingerol a potential biomarker for the consumption of these foods. While the biosynthesis of 6-gingerol is not fully elucidated, plausible pathways are presented here. It is speculated that some polyketide synthases (PKS) and reductases are involved in final synthesis of 6-Gingerol (10). 4-coumarate:CoA ligase (4CL) is then used to get p-Coumaroyl-CoA (5).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6g [6]-Gingerol	HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanone	HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-one	HMDB
6-Gingerol	HMDB
[6]-Gingerol	HMDB
(6)-Gingerol	HMDB
10-Gingerol	HMDB

Chemical Formula

C₁₇H₂₆O₄

Average Molecular Weight

294.3859

Monoisotopic Molecular Weight

294.18310932

IUPAC Name

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Traditional Name

gingerol

CAS Registry Number

58253-27-3

SMILES

CCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3

InChI Key

NLDDIKRKFXEWBK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Gingerol
Fatty alcohol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Beta-hydroxy ketone
Fatty acyl
Ketone
Secondary alcohol
Ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a phenylpropanoid (CPD-13494 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	30 - 32 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	3.45	ALOGPS
logP	3.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	83.11 m³·mol⁻¹	ChemAxon
Polarizability	33.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-3910000000-3c07be71d662410144ab	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-3910000000-3c07be71d662410144ab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-6900000000-9e3ae5652d5b17b9016d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-7119300000-fbff188e294cacd919c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0920000000-010ef6242d9f56fa2a72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-36e283e52cb0ba857d0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-35209ecc08a0fcbe3338	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-1900000000-aefaf0623f9721907b4d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00du-6900000000-50259fc38798f2830932	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0290000000-da571dea1713ff08f13b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-4930000000-922f5386fa26a96a1bbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9400000000-e27c462b7ff389743a4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0290000000-d356007500cff17f32ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-3930000000-be6a576d74a0f97fb8fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-5900000000-31f35b868a26cada9bf5	Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gingerol

METLIN ID

Not Available

PubChem Compound

3473

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Gingerol (HMDB0005783)

Structure for HMDB0005783 (Gingerol)