Showing Compound Card for Ascorbic acid (CDB004789)

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Record Information
Version1.0
Created at2020-04-17 18:36:56 UTC
Updated at2020-12-07 19:10:56 UTC
CannabisDB IDCDB004789
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAscorbic acid
DescriptionAscorbic acid, also known as acide ascorbique or L-ascorbate, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Ascorbic acid is a drug which is used to treat vitamin c deficiency, scurvy, delayed wound and bone healing, urine acidification, and in general as an antioxidant. it has also been suggested to be an effective antiviral agent. Ascorbic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). dopamine and ascorbic acid can be converted into norepinephrine and dehydroascorbic acid through the action of the enzyme dopamine beta-hydroxylase. In humans, ascorbic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Ascorbic acid is a very mild and grassy tasting compound. Outside of the human body, Ascorbic acid is found, on average, in the highest concentration within a few different foods, such as acerola, pepper (c. frutescens), and orange bell peppers and in a lower concentration in yogurts, yardlong beans, and peanuts. Ascorbic acid has also been detected, but not quantified in, several different foods, such as deerberries, cetacea (dolphin, porpoise, whale), acorns, lemon balms, and gelatins. This could make ascorbic acid a potential biomarker for the consumption of these foods. The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate. Ascorbic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC6H8O6
Average Molecular Weight176.12
Monoisotopic Molecular Weight176.0321
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional Namevitamin C
CAS Registry Number50-81-7
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
InChI KeyCIWBSHSKHKDKBQ-JLAZNSOCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Carboxylic acid ester
  • Enediol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility400 mg/mL at 40 °CMERCK INDEX (1996)
logP-1.85AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.9ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.03 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Solute carrier family 23 member 1SLC23A15q31.2Q9UHI7 details
Solute carrier family 23 member 2SLC23A220p13Q9UGH3 details
Solute carrier family 23 member 3SLC23A32q35Q6PIS1 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Egl nine homolog 2EGLN219q13.2Q96KS0 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Egl nine homolog 1EGLN11q42.1Q9GZT9 details
Egl nine homolog 2EGLN219q13.2Q96KS0 details
Egl nine homolog 3EGLN314q13.1Q9H6Z9 details
Concentrations Data
Not Available
HMDB IDHMDB0014273
DrugBank IDDB00126
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001224
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01041
BioCyc IDASCORBATE
BiGG IDNot Available
Wikipedia LinkAscorbic_Acid
METLIN IDNot Available
PubChem Compound54670067
PDB IDNot Available
ChEBI ID29073
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 53 proteins in total.

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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. Phytanoyl-CoA dioxygenase, peroxisomal
General function:
Involved in electron carrier activity
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
PHYH
Uniprot ID:
O14832
Molecular weight:
38538.065
Enzyme Details
4. Prolyl 4-hydroxylase subunit alpha-2
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA2
Uniprot ID:
O15460
Molecular weight:
60632.19
Enzyme Details
5. Prolyl 4-hydroxylase subunit alpha-1
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA1
Uniprot ID:
P13674
Molecular weight:
60966.645
Enzyme Details
6. Lactase-phlorizin hydrolase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
Enzyme Details
7. Gamma-butyrobetaine dioxygenase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
Gene Name:
BBOX1
Uniprot ID:
O75936
Molecular weight:
44714.6
Enzyme Details
8. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD1
Uniprot ID:
Q02809
Molecular weight:
83549.55
Enzyme Details
9. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 2
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD2
Uniprot ID:
O00469
Molecular weight:
84685.07
Enzyme Details
10. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 3
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD3
Uniprot ID:
O60568
Molecular weight:
84784.505

Transporters

Enzyme Details
1. Solute carrier family 23 member 1
General function:
Involved in transporter activity
Specific function:
Sodium/ascorbate cotransporter. Mediates electrogenic uptake of vitamin C, with a stoichiometry of 2 Na(+) for each ascorbate
Gene Name:
SLC23A1
Uniprot ID:
Q9UHI7
Molecular weight:
64830.4
Enzyme Details
2. Solute carrier family 23 member 2
General function:
Nucleotide transport and metabolism
Specific function:
Sodium/ascorbate cotransporter. Mediates electrogenic uptake of vitamin C, with a stoichiometry of 2 Na(+) for each ascorbate
Gene Name:
SLC23A2
Uniprot ID:
Q9UGH3
Molecular weight:
70336.2
Enzyme Details
3. Solute carrier family 23 member 3
General function:
Involved in transporter activity
Specific function:
Not Available
Gene Name:
SLC23A3
Uniprot ID:
Q6PIS1
Molecular weight:
64529.9

Only showing the first 10 proteins. There are 53 proteins in total.

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