Cannabis Compound Database: Showing Compound Card for galacturonic acid (CDB000236)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:26:07 UTC

Updated at

2020-11-18 16:34:56 UTC

CannabisDB ID

CDB000236

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

galacturonic acid

Description

Galacturonic acid, also known as D-galacturonate or sodium pectate, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 position oxidized to a carboxylic acid. Galacturonic acid exists in all living species, ranging from bacteria to humans. Galacturonic acid has been found in higher concentrations in flaxseeds. It has also been detected but not quantified in several different foods, such as common grapes, cocoa beans, roselles, milk (cow), and figs. Galacturonic acid has also been found in Cannabis sativa (PMID: 6991645 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acid	ChEBI
D-Galacturonic acid	ChEBI
(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoate	Generator
D-Galacturonate	Generator
Galacturonate	Generator
DL-Galacturonic acid	HMDB
D-Galactopyranuronic acid	HMDB
Galacturonic acid, (D)-isomer	HMDB
Galacturonic acid, (alpha-D)-isomer	HMDB
Galacturonic acid, calcium, sodium salt, (D)-isomer	HMDB
Galacturonic acid, monosodium salt, (D)-isomer	HMDB
Aldehydo-D-galacturonate	HMDB
Polygalacturonic acid, aluminum salt	HMDB
Sodium pectate	HMDB
Galacturonan	HMDB
Homogalacturonan	HMDB
Pectic acid	HMDB
Polygalacturonic acid homopolymer	HMDB
Polygalacturonic acid, sulfated	HMDB
Calcium polygalacturonate	HMDB
Pectate	HMDB
Polygalacturonic acid	HMDB
Polygalacturonic acid, calcium salt	HMDB
Polygalacturonic acid, homopolymer sodium salt	HMDB
Sodium polygalacturonate	HMDB
Anhydrogalacturonic acid	HMDB
Calcium pectate	HMDB
Polygalacturonic acid, homopolymer (D)-isomer	HMDB
Aldehydo-D-galacturonic acid	HMDB
(DL)-Galacturonic acid	HMDB
(D)-Galacturonic acid	HMDB
Galacturonic acid	MeSH

Chemical Formula

C₆H₁₀O₇

Average Molecular Weight

194.14

Monoisotopic Molecular Weight

194.0427

IUPAC Name

(2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Traditional Name

aldehydo-D-galacturonic acid

CAS Registry Number

14982-50-4

SMILES

O[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1

InChI Key

IAJILQKETJEXLJ-RSJOWCBRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Hexose monosaccharide
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Monosaccharide
Fatty acyl
Hydroxy acid
Fatty acid
Alpha-hydroxy acid
Beta-hydroxy aldehyde
Alpha-hydroxyaldehyde
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Aldehyde
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-galacturonic acid (CHEBI:47962 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Biofluid and excreta:

Feces

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	159 °C	Wikipedia
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-3.2	ChemAxon
logS	-0.29	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.21 m³·mol⁻¹	ChemAxon
Polarizability	16.23 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
Predicted GC-MS	galacturonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-9800000000-1d25ab641e968717daf1	Spectrum
Predicted GC-MS	galacturonic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00n0-3139450000-1762a4c61557c689a607	Spectrum
Predicted GC-MS	galacturonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	galacturonic 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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-03e9-0900000000-04b6c8cb4b4b2c077202	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0lk9-9700000000-4260c2e124c927041b62	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-650b5bb9db964b1c3e87	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9410000000-180d0e747dbcb5b21b01	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056s-2900000000-86606b8382ffe403bc8e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9500000000-af67bc97552641417bee	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-205a7cff1e298283a080	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05p9-9700000000-ee070fab487c9f3e49b7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9400000000-284825e422ba9585f17b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-64d4f9d758e2a4eeba68	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01y5-7900000000-df218a4e340a0ff668c1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kl-9100000000-d22d4d2644d77203331d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9000000000-93301767b758d212114f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-9300000000-77aa1619935fe785e397	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-9000000000-da4be7e32a829503c021	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9000000000-c1c9308cd925f43d015f	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 2B4	UGT2B4	4q13	P06133	details
UDP-glucuronosyltransferase 1-4	UGT1A4	2q37	P22310	details
UDP-glucuronosyltransferase 2B7	UGT2B7	4q13	P16662	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
UDP-glucuronosyltransferase 1-9	UGT1A9	2q37	O60656	details
UDP-glucuronosyltransferase 1-6	UGT1A6	2q37	P19224	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0002545

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

D-Galacturonic acid

METLIN ID

6713

PubChem Compound

84740

PDB ID

Not Available

ChEBI ID

47962

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

5. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Enzyme Details

6. UDP-glucuronosyltransferase 1-6

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A6
Uniprot ID:: P19224
Molecular weight:: 60750.215

Showing Compound Card for galacturonic acid (CDB000236)

Structure for CDB000236 (galacturonic acid)

Enzymes