Cannabis Compound Database: Showing Compound Card for Dehydroascorbic acid (CDB005216)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:20:58 UTC

Updated at

2020-11-18 16:39:32 UTC

CannabisDB ID

CDB005216

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dehydroascorbic acid

Description

Dehydroascorbic acid, also known as dehydroascorbate or DHAA, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids. Dehydroascorbic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydroascorbic acid exists in all living organisms, ranging from bacteria to humans. Recycling of ascorbate via active transport of DHA into cells, followed by reduction and reuse, mitigates the inability of humans to synthesize it from glucose. norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In humans, dehydroascorbic acid is involved in the metabolic disorder called hawkinsinuria. Solutions in water containing ascorbic acid and copper ions and/or peroxide, resulting in rapid oxidation of ascorbic acid to dehydroascorbic acid, have been shown to possess powerful but short-lived antimicrobial, antifungal, and antiviral properties, and have been used to treat gingivitis, periodontal disease, and dental plaque. The actual structure shown by spectroscopic studies is the result of rapid hemiacetal formation between the 6-OH and the 3-carbonyl groups. The lifetime of the stabilized species is commonly said to be about 6 minutes under biological conditions. Dehydroascorbic 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
Dehydroascorbate	Generator
1-Dehydroascorbate	HMDB
1-Dehydroascorbic acid	HMDB
Dehydro-L-ascorbate	HMDB
Dehydro-L-ascorbic acid	HMDB
DHAA	HMDB
L-Dehydroascorbate	HMDB
L-Dehydroascorbic acid	HMDB
L-Threo-2,3-hexodiulosonic acid gamma-lactone	HMDB
L-Threo-hexo-2,3-diulosono-1,4-lactone	HMDB
Oxidized ascorbate	HMDB
Oxidized ascorbic acid	HMDB
Oxidized vitamin C	HMDB
Dehydroerythorbic acid	HMDB

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.11

Monoisotopic Molecular Weight

174.0164

IUPAC Name

(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

Traditional Name

(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

CAS Registry Number

490-83-5

SMILES

[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO

InChI Identifier

InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1

InChI Key

SBJKKFFYIZUCET-DUZGATOHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

3-furanone
Gamma butyrolactone
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-0.67	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.55 m³·mol⁻¹	ChemAxon
Polarizability	14.02 Å³	ChemAxon
Number of Rings	1	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	Dehydroascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9200000000-0a414c4d59046ece51c1	Spectrum
Predicted GC-MS	Dehydroascorbic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fki-9831000000-c4b46024e1624e983ac3	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-4900000000-25a652482451303b3ca4	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-f1d23791c8a7b59576a3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-2900000000-5ebc67e43b07167f34cb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9000000000-27ae8f5e1795d4f732a8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-0900000000-ee719ada45193fc650a0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mbc-1900000000-d54b8e72e08e6ea1f7c0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9200000000-d07ff0053ddc28ce1915	2017-09-01	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		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
Peptidyl-glycine alpha-amidating monooxygenase	PAM	5q14-q21	P19021	details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details
Glutathione S-transferase omega-1	GSTO1	10q25.1	P78417	details
Glutathione S-transferase omega-2	GSTO2	10q25.1	Q9H4Y5	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Peptidyl-glycine alpha-amidating monooxygenase	PAM	5q14-q21	P19021	details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021459

KNApSAcK ID

Not Available

Chemspider ID

182283

KEGG Compound ID

C00425

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17242

References

General References

Not Available

Enzymes

Enzyme Details

1. Peptidyl-glycine alpha-amidating monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:: PAM
Uniprot ID:: P19021
Molecular weight:: 108402.425

Enzyme Details

2. Dopamine beta-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of dopamine to noradrenaline.
Gene Name:: DBH
Uniprot ID:: P09172
Molecular weight:: 69064.45

Enzyme Details

3. Glutathione S-transferase omega-1

General function:: Involved in glutathione transferase activity
Specific function:: Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:: GSTO1
Uniprot ID:: P78417
Molecular weight:: 27565.6

Enzyme Details

4. Glutathione S-transferase omega-2

General function:: Involved in glutathione transferase activity
Specific function:: Exhibits glutathione-dependent thiol transferase activity. Has high dehydroascorbate reductase activity and may contribute to the recycling of ascorbic acid. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA).
Gene Name:: GSTO2
Uniprot ID:: Q9H4Y5
Molecular weight:: 24399.09

Showing Compound Card for Dehydroascorbic acid (CDB005216)

Structure for CDB005216 (Dehydroascorbic acid)

Enzymes