Page last updated: 2024-10-24

L-ascorbic acid binding

Definition

Target type: molecularfunction

Binding to L-ascorbic acid, (2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate; L-ascorbic acid is vitamin C and has co-factor and anti-oxidant activities in many species. [GOC:mah]

L-Ascorbic acid binding is a molecular function that involves the interaction of a protein or other molecule with the vitamin L-ascorbic acid, also known as vitamin C. This interaction is crucial for a variety of biological processes, including:

- **Antioxidant defense:** L-ascorbic acid is a powerful antioxidant that can neutralize free radicals, protecting cells from damage. Proteins that bind L-ascorbic acid often participate in this antioxidant defense mechanism.
- **Collagen synthesis:** L-ascorbic acid is a cofactor for enzymes involved in collagen synthesis, such as prolyl hydroxylase. By binding to these enzymes, L-ascorbic acid facilitates their proper function, which is essential for the formation of strong, stable collagen.
- **Immune function:** L-ascorbic acid plays a vital role in the immune system, supporting the production of white blood cells and enhancing their ability to fight infections. Proteins that bind L-ascorbic acid can influence this immune response.
- **Iron metabolism:** L-ascorbic acid aids in the absorption and utilization of iron in the body. Proteins that bind L-ascorbic acid may be involved in this iron transport and metabolism.
- **Other metabolic processes:** L-ascorbic acid is involved in numerous other metabolic processes, including the biosynthesis of neurotransmitters, the formation of bile acids, and the metabolism of certain drugs. Proteins that bind L-ascorbic acid may play roles in these diverse functions.

The specific molecular details of L-ascorbic acid binding vary depending on the protein or molecule involved. However, in general, the interaction is often characterized by hydrogen bonding and other non-covalent interactions that create a stable complex. The binding site on the protein typically includes residues that are able to interact with the hydroxyl groups and other functional groups present in the L-ascorbic acid molecule.

The study of L-ascorbic acid binding is essential for understanding the roles of vitamin C in biological systems and for developing therapies that target these pathways.'
"

Proteins (10)

ProteinDefinitionTaxonomy
Dopamine beta-hydroxylase A dopamine beta-hydroxylase that is encoded in the genome of cow. [OMA:P15101, PRO:DNx]Bos taurus (cattle)
Prolyl 4-hydroxylase subunit alpha-1[no definition available]Gallus gallus (chicken)
Transmembrane prolyl 4-hydroxylaseA transmembrane prolyl 4-hydroxylase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9NXG6]Homo sapiens (human)
Prolyl hydroxylase EGLN3A prolyl hydroxylase EGLN3 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9H6Z9]Homo sapiens (human)
Egl nine homolog 1An egl nine homolog 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9GZT9]Homo sapiens (human)
Prolyl hydroxylase EGLN2A prolyl hydroxylase EGLN2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q96KS0]Homo sapiens (human)
Prolyl 3-hydroxylase OGFOD1A prolyl 3-hydroxylase OGFOD1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q8N543]Homo sapiens (human)
Peptidyl-glycine alpha-amidating monooxygenaseA peptidyl-glycine alpha-amidating monooxygenase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P19021]Homo sapiens (human)
Prolyl 4-hydroxylase subunit alpha-1A prolyl 4-hydroxylase subunit alpha-1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P13674]Homo sapiens (human)
Dopamine beta-hydroxylaseA dopamine beta-hydroxylase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P09172]Homo sapiens (human)

Compounds (60)

CompoundDefinitionClassesRoles
2,3-dihydroxybenzoic acid2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.

2,3-dihydroxybenzoic acid: RN given refers to parent cpd

dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.
dihydroxybenzoic acidhuman xenobiotic metabolite;
plant metabolite
alpha-ketoglutaric acid2-oxoglutaric acid : An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle.oxo dicarboxylic acidfundamental metabolite
protocatechuic acid3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.

protocatechuic acid: RN given refers to parent cpd; structure
catechols;
dihydroxybenzoic acid
antineoplastic agent;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor;
human xenobiotic metabolite;
plant metabolite
4-hydroxybenzoic acid4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.monohydroxybenzoic acidalgal metabolite;
plant metabolite
catecholcatecholsallelochemical;
genotoxin;
plant metabolite
salicylic acidScalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
gallic acidgallate : A trihydroxybenzoate that is the conjugate base of gallic acid.trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
3,4-dihydroxyphenylacetic acid(3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.

3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.

dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.
catechols;
dihydroxyphenylacetic acid
human metabolite
glucono-1,4-lactonegamma-lactone
hydroquinonebenzenediol;
hydroquinones
antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
phenylacetic acidphenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.benzenes;
monocarboxylic acid;
phenylacetic acids
allergen;
Aspergillus metabolite;
auxin;
EC 6.4.1.1 (pyruvate carboxylase) inhibitor;
Escherichia coli metabolite;
human metabolite;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite;
toxin
picolinic acidpicolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.

picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206
pyridinemonocarboxylic acidhuman metabolite;
MALDI matrix material
pyrogallolbenzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.benzenetriol;
phenolic donor
plant metabolite
succinic acidsuccinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.

Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851)
alpha,omega-dicarboxylic acid;
C4-dicarboxylic acid
anti-ulcer drug;
fundamental metabolite;
micronutrient;
nutraceutical;
radiation protective agent
isocitric acidisocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.

isocitric acid: RN given refers to unlabeled parent cpd
secondary alcohol;
tricarboxylic acid
fundamental metabolite
mandelic acidSAMMA: mandelic acid condensation polymer2-hydroxy monocarboxylic acid;
benzenes
antibacterial agent;
human xenobiotic metabolite
2,2'-dipyridyl2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.

2,2'-Dipyridyl: A reagent used for the determination of iron.
bipyridinechelator;
ferroptosis inhibitor
beta-resorcylic acidbeta-resorcylic acid: RN given refers to parent cpd; structure
fusaric acidFusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.aromatic carboxylic acid;
pyridines
2,5-dihydroxybenzoic acid2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.

2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin
dihydroxybenzoic acidEC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
fungal metabolite;
human metabolite;
MALDI matrix material;
mouse metabolite
hypericin
resorcinolresorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.

resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951
benzenediol;
phenolic donor;
resorcinols
erythropoietin inhibitor;
sensitiser
succinylacetone4,6-dioxoheptanoic acid : A dioxo monocarboxylic acid that is heptanoic acid in which oxo groups replace the hydrogens at positions 4 and 6. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker for type 1 tyrosinaemia.

succinylacetone: inhibitor of heme biosynthesis
beta-diketone;
dioxo monocarboxylic acid
human metabolite
tyraminemonoamine molecular messenger;
primary amino compound;
tyramines
EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter
3-hydroxybenzoic acid3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.

3-hydroxybenzoic acid: RN given refers to parent cpd
monohydroxybenzoic acidbacterial metabolite;
plant metabolite
alpha-resorcylic acid3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.

alpha-resorcylic acid: RN given refers to parent cpd
dihydroxybenzoic acid;
resorcinols
metabolite
2,5-pyridinedicarboxylic acid2,5-Pyridinedicarboxylic acid: RN given refers to parent cpd

isocinchomeronic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 5.
pyridinedicarboxylic acid
gamma-resorcylic aciddihydroxybenzoic acidmetabolite
glycyrrhetinic acidcyclic terpene ketone;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid
immunomodulator;
plant metabolite
salicyluratesalicylurate : A monocarboxylic acid anion that is the conjugate base of salicyluric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.

salicylurate: RN given refers to parent cpd

salicyluric acid : An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.
N-acylglycine;
secondary carboxamide
human xenobiotic metabolite;
uremic toxin
2,4-pyridinedicarboxylic acidlutidinic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 4.pyridinedicarboxylic acid
oleanolic acidhydroxy monocarboxylic acid;
pentacyclic triterpenoid
plant metabolite
tropolonetropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.

Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).
alpha-hydroxy ketone;
cyclic ketone;
enol
bacterial metabolite;
fungicide;
toxin
aceturic acidaceturic acid: structure

N-acetylglycine : An N-acylglycine where the acyl group is specified as acetyl.
N-acetyl-amino acid;
N-acylglycine
human metabolite
daminozidedaminozide: induces tumorsstraight-chain fatty acid
3-phenylpropylamine3-phenylpropylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 3-aminopropyl group.benzenes;
phenylalkylamine;
primary amino compound
u 0521U 0521: catechol methyltransferase antagonist; structureacetophenones
7-hydroxytropolone7-hydroxytropolone: structure
4-vinylphenol4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.

4-vinylphenol: RN given refers to cpd with locants as specified
phenolshuman urinary metabolite;
human xenobiotic metabolite
ursolic acidhydroxy monocarboxylic acid;
pentacyclic triterpenoid
geroprotector;
plant metabolite
betulinic acidhydroxy monocarboxylic acid;
pentacyclic triterpenoid
anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
maslinic acid(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoriadihydroxy monocarboxylic acid;
pentacyclic triterpenoid
anti-inflammatory agent;
antineoplastic agent;
antioxidant;
plant metabolite
3,4-dihydroxymandelic acid3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.

3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation
2-hydroxy monocarboxylic acid;
catechols
antioxidant;
drug metabolite;
human metabolite;
mouse metabolite
3,7-dihydroxytropolone3,7-dihydroxytropolone : A cyclic ketone that is tropolone in which the hydrogens at positions 3 and 7 are substituted by hydroxy groups. It is isolated from the soil bacterium Streptomyces tropolofaciens strain K611-97.

3,7-dihydroxytropolone: from Streptomyces tropolofaciens; active against B16 melanoma; structure given in first source
alpha-hydroxy ketone;
cyclic ketone;
enol;
triol
antineoplastic agent;
bacterial metabolite
3,4-dihydroxyphenylpropionic acid3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.

3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure
(dihydroxyphenyl)propanoic acidantioxidant;
human xenobiotic metabolite
fumaric acidfumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.

fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters
butenedioic acidfood acidity regulator;
fundamental metabolite;
geroprotector
5-carboxy-8-hydroxyquinoline5-carboxy-8-hydroxyquinoline: a JmjC histone demethylase inhibitor; structure in first sourcequinolines
caffeic acidtrans-caffeic acid : The trans-isomer of caffeic acid.caffeic acidgeroprotector;
mouse metabolite
methimazolemethimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.

Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.
1,3-dihydroimidazole-2-thionesantithyroid drug
1-(4-hydroxybenzyl)imidazole-2-thiol1-(4-hydroxybenzyl)imidazole-2-thiol: RN & structure given in first source; RN not in Chemline 3/87
oxalylglycineN-oxalylglycine : An amino dicarboxylic acid that is iminodiacetic acid with an oxo substituent. It is used as an inhibitor of alpha-ketoglutarate dependent (EC 1.14.11.*) enzymes.

oxalylglycine: structure given in first source
amino dicarboxylic acid;
N-acylglycine
EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor
prolylglycineL-prolylglycine : A dipeptide consisting of glycine having an L-prolyl group attached to its alpha-amino nitrogen.

prolylglycine: RN given refers to (L)-isomer
dipeptide;
dipeptide zwitterion
phenylalanylglycinePhe-Gly : A dipeptide formed from L-phenylalanine and glycine residues.

phenylalanylglycine: RN given refers to (DL)-isomer
dipeptidemetabolite
sk&f 102698
fg-4592roxadustat : An N-acylglycine resulting from the formal condensation of the amino group of glycine with the carboxy group of 4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxylic acid. It is an inhibitor of hypoxia inducible factor prolyl hydroxylase (HIF-PH).

roxadustat: structure in first source
aromatic ether;
isoquinolines;
N-acylglycine
EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor;
EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor
jnj 42041935
ascorbic acidAscorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.

L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.

L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.

vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.
ascorbic acid;
vitamin C
coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
2-[[[4-hydroxy-2-oxo-1-(phenylmethyl)-3-quinolinyl]-oxomethyl]amino]acetic acidquinolines
bay 85-3934
gsk1278863daprodustat : A member of the class of barbiturates that is barbituric acid substituted by cyclohexyl groups at positions 1 and 3, and by a (carboxymethyl)aminocarbonyl group at position 5. It is an inhibitor of hypoxia-inducible factor prolyl hydroxylase developed by GlaxoSmithKline for the treatment of anaemia in patients with chronic kidney disease.

GSK1278863: a HIF prolyl hydroxylase inhibitor