Ascorbic acid
Relevant Data
Food Additives Approved in the United States
Food Additives Approved by WHO:
General Information
| Chemical name | Ascorbic acid |
| E No. | E 300 |
| INS. | 300 |
| CAS number | 50-81-7 |
| Group | No |
| Component of the group |
Group I, Additives (Group I) |
From webgate.ec.europa.eu
Authorisation of the use of this additive in Food Additives
The additive is authorised to be used in the following category(ies):
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From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 54670067 |
| IUPAC Name | (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one |
| InChI | 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 Key | CIWBSHSKHKDKBQ-JLAZNSOCSA-N |
| Canonical SMILES | C(C(C1C(=C(C(=O)O1)O)O)O)O |
| Molecular Formula | C6H8O6 |
| Wikipedia | Vitamin C |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 176.124 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Complexity | 232.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B g O A A A A A A A A A A A A A A A A A A A A Q A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C B S g g A I A C A A A B g C I A A D Q C A I A A A A g I A A A C A B A A E g B F A A A I A A C U A A F w A A L I Q J A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 107.0 |
| Monoisotopic Mass | 176.032 |
| Exact Mass | 176.032 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8532 |
| Human Intestinal Absorption | HIA+ | 0.6559 |
| Caco-2 Permeability | Caco2- | 0.7710 |
| P-glycoprotein Substrate | Non-substrate | 0.6077 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9097 |
| Non-inhibitor | 0.9807 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9008 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6194 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8133 |
| CYP450 2D6 Substrate | Non-substrate | 0.8696 |
| CYP450 3A4 Substrate | Non-substrate | 0.6361 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8958 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9478 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9347 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9383 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9662 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9249 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9676 |
| Non-inhibitor | 0.9286 | |
| AMES Toxicity | Non AMES toxic | 0.8941 |
| Carcinogens | Non-carcinogens | 0.9417 |
| Fish Toxicity | Low FHMT | 0.5982 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5093 |
| Honey Bee Toxicity | High HBT | 0.7536 |
| Biodegradation | Ready biodegradable | 0.9526 |
| Acute Oral Toxicity | IV | 0.5871 |
| Carcinogenicity (Three-class) | Non-required | 0.7591 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.1081 | LogS |
| Caco-2 Permeability | -0.3148 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3059 | LD50, mol/kg |
| Fish Toxicity | 1.5598 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.6529 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Dihydrofurans |
| Subclass | Furanones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Butenolides |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. |
From ClassyFire
Targets
- General Function:
- Transferase activity
- Specific Function:
- LPH splits lactose in the small intestine.
- Gene Name:
- LCT
- Uniprot ID:
- P09848
- Molecular Weight:
- 218584.77 Da
- General Function:
- Hyaluronate lyase activity
- Uniprot ID:
- Q54873
- Molecular Weight:
- 120770.645 Da
- General Function:
- Xylose isomerase activity
- Specific Function:
- Involved in D-xylose catabolism.
- Gene Name:
- xylA
- Uniprot ID:
- P24300
- Molecular Weight:
- 43226.915 Da
- General Function:
- Procollagen-lysine 5-dioxygenase 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 Da
- General Function:
- Phytanoyl-coa dioxygenase activity
- Specific Function:
- Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
- Gene Name:
- PHYH
- Uniprot ID:
- O14832
- Molecular Weight:
- 38538.065 Da
- General Function:
- Procollagen-lysine 5-dioxygenase 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 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
- Gene Name:
- BBOX1
- Uniprot ID:
- O75936
- Molecular Weight:
- 44714.6 Da
- General Function:
- L-ascorbic acid binding
- Specific Function:
- Conversion of dopamine to noradrenaline.
- Gene Name:
- DBH
- Uniprot ID:
- P09172
- Molecular Weight:
- 69064.45 Da
- General Function:
- Zinc ion binding
- 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:
- 108331.35 Da
- General Function:
- Procollagen-proline 4-dioxygenase 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:
- 61048.775 Da
- General Function:
- Protein complex binding
- Specific Function:
- Basement membrane-associated chondroitin sulfate proteoglycan (CSPG). Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens, especially types IV and V. May be involved in the secretory pathway of cells. Has growth suppressive activity in fibroblasts.
- Gene Name:
- P3H1
- Uniprot ID:
- Q32P28
- Molecular Weight:
- 83393.195 Da
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
- Gene Name:
- OGFOD2
- Uniprot ID:
- Q6N063
- Molecular Weight:
- 38996.065 Da
- General Function:
- Ferrous iron binding
- Specific Function:
- Dioxygenase that repairs alkylated DNA and RNA containing 1-methyladenine and 3-methylcytosine by oxidative demethylation. Can also repair alkylated DNA containing 1-ethenoadenine (in vitro). Has strong preference for double-stranded DNA. Has low efficiency with single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron.
- Gene Name:
- ALKBH2
- Uniprot ID:
- Q6NS38
- Molecular Weight:
- 29322.22 Da
- General Function:
- Procollagen-proline 3-dioxygenase activity
- Specific Function:
- Shows prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types II, IV and V.
- Gene Name:
- P3H2
- Uniprot ID:
- Q8IVL5
- Molecular Weight:
- 80983.685 Da
- General Function:
- Procollagen-proline 3-dioxygenase activity
- Specific Function:
- Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types IV and V.
- Gene Name:
- P3H3
- Uniprot ID:
- Q8IVL6
- Molecular Weight:
- 81835.705 Da
- General Function:
- Peptidyl-proline dioxygenase activity
- Specific Function:
- Prolyl 3-hydroxylase that catalyzes 3-hydroxylation of 'Pro-62' of small ribosomal subunit RPS23, thereby regulating protein translation termination efficiency. Involved in stress granule formation.
- Gene Name:
- OGFOD1
- Uniprot ID:
- Q8N543
- Molecular Weight:
- 63245.655 Da
- General Function:
- Peptidyl-proline 4-dioxygenase activity
- Specific Function:
- Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific proline found in each of the oxygen-dependent degradation (ODD) domains (N-terminal, NODD, and C-terminal, CODD) of HIF1A. Also hydroxylates HIF2A. Has a preference for the CODD site for both HIF1A and HIF2A. Hydroxylated HIFs are then targeted for proteasomal degradation via the von Hippel-Lindau ubiquitination complex. Under hypoxic conditions, the hydroxylation reaction is attenuated allowing HIFs to escape degradation resulting in their translocation to the nucleus, heterodimerization with HIF1B, and increased expression of hypoxy-inducible genes. EGLN2 is involved in regulating hypoxia tolerance and apoptosis in cardiac and skeletal muscle. Also regulates susceptibility to normoxic oxidative neuronal death. Links oxygen sensing to cell cycle and primary cilia formation by hydroxylating the critical centrosome component CEP192 which promotes its ubiquitination and subsequent proteasomal degradation. Hydroxylates IKBKB, mediating NF-kappaB activation in hypoxic conditions. Target proteins are preferentially recognized via a LXXLAP motif.
- Gene Name:
- EGLN2
- Uniprot ID:
- Q96KS0
- Molecular Weight:
- 43650.03 Da
- General Function:
- L-ascorbic acid binding
- Specific Function:
- Dioxygenase that repairs alkylated DNA containing 1-methyladenine (1meA) and 3-methylcytosine (3meC) by oxidative demethylation. Has a strong preference for single-stranded DNA. Able to process alkylated 3mC within double-stranded regions via its interaction with ASCC3, which promotes DNA unwinding to generate single-stranded substrate needed for ALKHB3. May also act on RNA. Requires molecular oxygen, alpha-ketoglutarate and iron.
- Gene Name:
- ALKBH3
- Uniprot ID:
- Q96Q83
- Molecular Weight:
- 33374.495 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Histone demethylase that specifically demethylates 'Lys-4' of histone H3, thereby playing a central role in histone code. Does not demethylate histone H3 'Lys-9', H3 'Lys-27', H3 'Lys-36', H3 'Lys-79' or H4 'Lys-20'. Demethylates trimethylated and dimethylated but not monomethylated H3 'Lys-4'. May play a role in spermatogenesis.
- Gene Name:
- KDM5D
- Uniprot ID:
- Q9BY66
- Molecular Weight:
- 174071.34 Da
- General Function:
- Peptidyl-proline dioxygenase activity
- Specific Function:
- Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific proline found in each of the oxygen-dependent degradation (ODD) domains (N-terminal, NODD, and C-terminal, CODD) of HIF1A. Also hydroxylates HIF2A. Has a preference for the CODD site for both HIF1A and HIF1B. Hydroxylated HIFs are then targeted for proteasomal degradation via the von Hippel-Lindau ubiquitination complex. Under hypoxic conditions, the hydroxylation reaction is attenuated allowing HIFs to escape degradation resulting in their translocation to the nucleus, heterodimerization with HIF1B, and increased expression of hypoxy-inducible genes. EGLN1 is the most important isozyme under normoxia and, through regulating the stability of HIF1, involved in various hypoxia-influenced processes such as angiogenesis in retinal and cardiac functionality. Target proteins are preferentially recognized via a LXXLAP motif.
- Gene Name:
- EGLN1
- Uniprot ID:
- Q9GZT9
- Molecular Weight:
- 46020.585 Da
- General Function:
- Sodium-dependent l-ascorbate transmembrane 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:
- 64830.445 Da
- General Function:
- Protein homodimerization 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 Da
- General Function:
- Peptidyl-proline 4-dioxygenase activity
- Specific Function:
- Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific proline found in each of the oxygen-dependent degradation (ODD) domains (N-terminal, NODD, and C-terminal, CODD) of HIF1A. Also hydroxylates HIF2A. Has a preference for the CODD site for both HIF1A and HIF2A. Hydroxylation on the NODD site by EGLN3 appears to require prior hydroxylation on the CODD site. Hydroxylated HIFs are then targeted for proteasomal degradation via the von Hippel-Lindau ubiquitination complex. Under hypoxic conditions, the hydroxylation reaction is attenuated allowing HIFs to escape degradation resulting in their translocation to the nucleus, heterodimerization with HIF1B, and increased expression of hypoxy-inducible genes. EGLN3 is the most important isozyme in limiting physiological activation of HIFs (particularly HIF2A) in hypoxia. Also hydroxylates PKM in hypoxia, limiting glycolysis. Under normoxia, hydroxylates and regulates the stability of ADRB2. Regulator of cardiomyocyte and neuronal apoptosis. In cardiomyocytes, inhibits the anti-apoptotic effect of BCL2 by disrupting the BAX-BCL2 complex. In neurons, has a NGF-induced proapoptotic effect, probably through regulating CASP3 activity. Also essential for hypoxic regulation of neutrophilic inflammation. Plays a crucial role in DNA damage response (DDR) by hydroxylating TELO2, promoting its interaction with ATR which is required for activation of the ATR/CHK1/p53 pathway. Target proteins are preferentially recognized via a LXXLAP motif.
- Gene Name:
- EGLN3
- Uniprot ID:
- Q9H6Z9
- Molecular Weight:
- 27261.06 Da
- General Function:
- Trimethyllysine dioxygenase activity
- Specific Function:
- Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
- Gene Name:
- TMLHE
- Uniprot ID:
- Q9NVH6
- Molecular Weight:
- 49517.2 Da
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, 2-oxoglutarate as one donor, and incorporation of one atom each of oxygen into both donors
- Specific Function:
- Catalyzes the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates HIF1A at 'Pro-402' and 'Pro-564'. May function as a cellular oxygen sensor and, under normoxic conditions, may target HIF through the hydroxylation for proteasomal degradation via the von Hippel-Lindau ubiquitination complex.
- Gene Name:
- P4HTM
- Uniprot ID:
- Q9NXG6
- Molecular Weight:
- 56660.535 Da
From T3DB