Ascorbic acid (ECMDB00044) (M2MDB000013)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (6)Transporters (5)XML
Proteins (319)
Record Information
Version2.0
Creation Date2012-05-31 09:55:53 -0600
Update Date2015-09-17 15:41:01 -0600
Secondary Accession Numbers
  • ECMDB00044
Identification
Name:Ascorbic acid
DescriptionAscorbic acid is the biologically active form of vitamin C. Ascorbic acid is an electron donor for enzymes involved in the biosynthesis of carnitine and tyrosine metabolism. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (+)-ascorbate
  • (+)-ascorbic acid
  • (+)-Sodium L-ascorbate
  • (+)-Sodium L-ascorbic acid
  • 3-Keto-L-gulofuranolactone
  • 3-Oxo-L-gulofuranolactone
  • Adenex
  • Allercorb
  • Antiscorbic vitamin
  • Antiscorbutic vitamin
  • Arco-cee
  • Ascoltin
  • Ascor-B.I.D.
  • Ascorb
  • Ascorbajen
  • Ascorbate
  • Ascorbic acid
  • Ascorbicab
  • Ascorbicap
  • Ascorbicin
  • Ascorbin
  • Ascorbutina
  • Ascorin
  • Ascorteal
  • Ascorvit
  • C-Level
  • C-Long
  • C-Quin
  • C-Span
  • C-Vimin
  • Cantan
  • Cantaxin
  • Catavin C
  • Ce lent
  • Ce-mi-lin
  • Ce-vi-sol
  • Cebicure
  • Cebid
  • Cebion
  • Cebione
  • Cecon
  • Cee-caps TD
  • Cee-vite
  • Cegiolan
  • Ceglion
  • Ceklin
  • Celaskon
  • Celin
  • Cell C
  • Cemagyl
  • Cemill
  • Cenetone
  • Cenolate
  • Cenolic acid
  • Cereon
  • Cergona
  • Cescorbat
  • Cetamid
  • Cetane
  • Cetane-caps TC
  • Cetane-caps TD
  • Cetebe
  • Cetemican
  • Cevalin
  • Cevatine
  • Cevex
  • Cevi-bid
  • Cevimin
  • Cevital
  • Cevitamate
  • Cevitamic acid
  • Cevitamin
  • Cevitan
  • Cevitex
  • Cewin
  • Chewcee
  • Ciamin
  • Cipca
  • Citriscorb
  • Citrovit
  • Colascor
  • Concemin
  • Davitamon C
  • Dora-C-500
  • Duoscorb
  • Ferrous ascorbate
  • Ferrous ascorbic acid
  • g-Lactone L-threo-hex-2-enonate
  • g-Lactone L-threo-hex-2-enonic acid
  • Gamma-Lactone L-threo-Hex-2-enonate
  • Gamma-Lactone L-threo-Hex-2-enonic acid
  • Hexuronate
  • Hexuronic acid
  • HiCee
  • Hybrin
  • Ido-C
  • Juvamine
  • Kangbingfeng
  • Kyselina askorbova
  • L(+)-Ascorbate
  • L(+)-Ascorbic acid
  • L-(+)-Ascorbate
  • L-(+)-Ascorbic acid
  • L-3-Ketothreohexuronate lactone
  • L-3-Ketothreohexuronic acid lactone
  • L-Ascorbate
  • L-Ascorbate (vitamin C)
  • L-Ascorbic acid
  • L-Ascorbic acid (vitamin C)
  • L-Lyxoascorbate
  • L-Lyxoascorbic acid
  • L-Threo-ascorbate
  • L-Threo-ascorbic acid
  • L-Xyloascorbate
  • L-Xyloascorbic acid
  • Laroscorbine
  • Lemascorb
  • Liqui-cee
  • Meri-c
  • Natrascorb
  • Natrascorb injectable
  • Planavit C
  • Proscorbin
  • Redoxon
  • Ribena
  • Ronotec 100
  • Rontex 100
  • Roscorbic
  • Rovimix C
  • Scorbacid
  • Scorbu C
  • Scorbu-C
  • Secorbate
  • Secorbic acid
  • Sodascorbate
  • Sodascorbic acid
  • Suncoat VC 40
  • Testascorbic
  • VASC
  • Vicelat
  • Vicin
  • Vicomin C
  • Viforcit
  • Viscorin
  • Viscorin 100M
  • Vitace
  • Vitacee
  • Vitacimin
  • Vitacin
  • Vitamin C
  • Vitamisin
  • Vitascorbol
  • Xitix
  • γ-Lactone L-threo-hex-2-enonate
  • γ-Lactone L-threo-hex-2-enonic acid
Chemical Formula:C6H8O6
Weight:Average: 176.1241
Monoisotopic: 176.032087988
InChI Key:CIWBSHSKHKDKBQ-JLAZNSOCSA-N
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
CAS number:50-81-7
IUPAC Name:(2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2,3-dihydrofuran-3-one
Traditional IUPAC Name:(2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2H-furan-3-one
SMILES:[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous acid
  • Vinylogous ester
  • 1,2-diol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Oxacycle
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:191 °C
Experimental Properties:
PropertyValueSource
Water Solubility:400 mg/mL at 40 oC [MERCK INDEX (1996)]PhysProp
LogP:-1.85 [AVDEEF,A (1997)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility257 g/LALOGPS
logP-1.9ALOGPS
logP-1.3ChemAxon
logS0.16ALOGPS
pKa (Strongest Acidic)0.72ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.26 m³·mol⁻¹ChemAxon
Polarizability14.98 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid
Protein N(pi)-phospho-L-histidine + Ascorbic acid <> Protein histidine + L-Ascorbate 6-phosphate
an oxidized electron acceptor + Ascorbic acid + Hydrogen ion > a reduced electron acceptor + monodehydroascorbate
Ascorbic acid + Hydrogen peroxide > monodehydroascorbate + Water
monodehydroascorbate + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate
Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid
Ascorbic acid + Hydrogen peroxide + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate + Water
Ascorbic acid + Hydrogen peroxide + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate + Water
Ascorbic acid + HPr - phosphorylated + Ascorbic acid > L-ascorbate 6-phosphate + HPr + L-Ascorbate 6-phosphate
SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • L-ascorbate degradation II (bacterial, aerobic) PWY-6961
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0005-9700000000-7a799a3b3b979d9598d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052k-9000000000-450579c53a443c3cececView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-06b81a073ca87770c390View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID29073
HMDB IDHMDB00044
Pubchem Compound ID644104
Kegg IDC00072
ChemSpider ID559144
WikipediaAscorbic acid
BioCyc IDASCORBATE
EcoCyc IDASCORBATE

Enzymes

Protein Details
1. Phosphoenolpyruvate-protein phosphotransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein Details
2. Putative phosphotransferase enzyme IIA component yadI
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane
Gene Name:
yadI
Uniprot ID:
P36881
Molecular weight:
16540
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
3. Ascorbate-specific phosphotransferase enzyme IIA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaC
Uniprot ID:
P69820
Molecular weight:
17237
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
4. Ascorbate-specific phosphotransferase enzyme IIB component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaB
Uniprot ID:
P69822
Molecular weight:
10896
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
5. Ascorbate-specific permease IIC component ulaA
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaA
Uniprot ID:
P39301
Molecular weight:
50737
Protein Details
6. Phosphocarrier protein HPr
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

Protein Details
1. Ascorbate-specific permease IIC component ulaA
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaA
Uniprot ID:
P39301
Molecular weight:
50737
Protein Details
2. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
3. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
4. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
5. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368