L-ascorbic acid (CHEBI:29073)

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CHEBI:29073 - L-ascorbic acid

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ChEBI Name	L-ascorbic acid

ChEBI ID	CHEBI:29073

ChEBI ASCII Name	L-ascorbic acid

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

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:2868, CHEBI:43473, CHEBI:40892, CHEBI:17208, CHEBI:21240

Supplier Information	ChemicalBook:CB2185552, ZINC000008215481

Download	Molfile XML SDF

more structures >>

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20 20 0 0 0 0 999 V2000

2.1460 -3.5372 1.5363 C 0 0 2 0 0 0 0 0 0 0 0 0

2.6985 -4.6232 2.4384 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3296 -2.9255 0.9845 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3154 -2.5163 2.3229 C 0 0 2 0 0 0 0 0 0 0 0 0

4.0254 -4.6232 2.3916 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9452 -5.4808 3.1776 O 0 0 0 0 0 0 0 0 0 0 0 0

4.4235 -3.5701 1.4924 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7728 -1.4526 1.3667 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1357 -1.8974 3.3028 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8550 -5.4623 3.0673 O 0 0 0 0 0 0 0 0 0 0 0 0

5.5702 -3.2940 1.2228 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8561 -0.8035 0.7186 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4980 -3.9285 0.7230 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4941 -3.0063 2.8882 H 0 0 0 0 0 0 0 0 0 0 0 0

2.3942 -6.1861 3.7479 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1922 -0.6818 1.9175 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1312 -1.9115 0.5843 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8966 -1.9718 4.2832 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8577 -5.3772 2.9600 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9270 -0.8230 -0.2907 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

2 5 2 0 0 0 0

2 6 1 0 0 0 0

3 7 1 0 0 0 0

4 8 1 0 0 0 0

4 9 1 0 0 0 0

5 7 1 0 0 0 0

5 10 1 0 0 0 0

7 11 2 0 0 0 0

8 12 1 0 0 0 0

13 1 1 0 0 0 0

14 4 1 0 0 0 0

15 6 1 0 0 0 0

16 8 1 0 0 0 0

17 8 1 0 0 0 0

18 9 1 0 0 0 0

19 10 1 0 0 0 0

20 12 1 0 0 0 0

M END): 19 ms

reading 20 atoms

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Wikipedia	License
Guanosine diphosphate, abbreviated GDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of a pyrophosphate group, a pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g., the G-proteins that are involved in signal transduction. GDP is converted into GTP with the help of pyruvate kinase and phosphoenolpyruvate.
Read full article at Wikipedia

Formula

C6H8O6

Net Charge

Average Mass

176.12410

Monoisotopic Mass

176.03209

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

InChIKey

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO

Metabolite of Species	Details
Arabidopsis thaliana (NCBI:txid3702)	See: DOI

Roles Classification
Chemical Role(s):	food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	coenzyme A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. food colour retention agent A food additive that intensifies, retains or stabilises the colour of a food. cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). flour treatment agent A food additive which is added to flour or dough to improve baking quality and/or colour. food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via vitamin C )

Application(s):	skin lightening agent Any cosmetic used to lighten the colour of skin by reducing the concentration of melanin. food colour retention agent A food additive that intensifies, retains or stabilises the colour of a food. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. flour treatment agent A food additive which is added to flour or dough to improve baking quality and/or colour. food antioxidant An antioxidant that used as a food additives to help guard against food deterioration.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-ascorbic acid (CHEBI:29073) has role coenzyme (CHEBI:23354) L-ascorbic acid (CHEBI:29073) has role cofactor (CHEBI:23357) L-ascorbic acid (CHEBI:29073) has role flour treatment agent (CHEBI:64577) L-ascorbic acid (CHEBI:29073) has role food antioxidant (CHEBI:77962) L-ascorbic acid (CHEBI:29073) has role food colour retention agent (CHEBI:78006) L-ascorbic acid (CHEBI:29073) has role geroprotector (CHEBI:176497) L-ascorbic acid (CHEBI:29073) has role plant metabolite (CHEBI:76924) L-ascorbic acid (CHEBI:29073) has role skin lightening agent (CHEBI:85046) L-ascorbic acid (CHEBI:29073) is a ascorbic acid (CHEBI:22652) L-ascorbic acid (CHEBI:29073) is a vitamin C (CHEBI:176783) L-ascorbic acid (CHEBI:29073) is conjugate acid of L-ascorbate (CHEBI:38290) L-ascorbic acid (CHEBI:29073) is enantiomer of D-ascorbic acid (CHEBI:51384)

Incoming	1,12-di-L-ascorbyl dodecanedioate (CHEBI:59753) has functional parent L-ascorbic acid (CHEBI:29073) L-ascorbic acid 2-phosphate (CHEBI:167162) has functional parent L-ascorbic acid (CHEBI:29073) L-ascorbic acid 6-phosphate (CHEBI:61701) has functional parent L-ascorbic acid (CHEBI:29073) L-dehydroascorbic acid (CHEBI:27956) has functional parent L-ascorbic acid (CHEBI:29073) ascorbigen (CHEBI:64944) has functional parent L-ascorbic acid (CHEBI:29073) ascorbyl dipalmitate (CHEBI:85080) has functional parent L-ascorbic acid (CHEBI:29073) L-ascorbate (CHEBI:38290) is conjugate base of L-ascorbic acid (CHEBI:29073) D-ascorbic acid (CHEBI:51384) is enantiomer of L-ascorbic acid (CHEBI:29073)

IUPAC Names

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one

L-threo-hex-2-enono-1,4-lactone

INNs	Sources
acide ascorbique	ChemIDplus
ácido ascórbico	ChemIDplus
acidum ascorbicum	ChemIDplus
ascorbic acid	KEGG DRUG

Synonyms	Sources
acidum ascorbinicum	ChemIDplus
ASCORBIC ACID	PDBeChem
Ascorbic acid	KEGG COMPOUND
Ascorbicap	KEGG DRUG
Ascorbinsäure	ChEBI
E 300	ChEBI
E-300	ChEBI
E300	ChEBI
L-(+)-ascorbic acid	NIST Chemistry WebBook
L-Ascorbate	KEGG COMPOUND
L-Ascorbic acid	KEGG COMPOUND
Vitamin C	KEGG COMPOUND

Brand Name	Source
Ascoltin	KEGG DRUG

Manual Xrefs	Databases
2405	BPDB
4072	DrugCentral
ASC	PDBeChem
ASCORBATE	MetaCyc
Ascorbic_Acid	Wikipedia
C00001179	KNApSAcK
C00072	KEGG COMPOUND
D00018	KEGG DRUG
DB00126	DrugBank
HMDB0000044	HMDB
View more database links

Registry Numbers	Types	Sources
4087	Gmelin Registry Number	Gmelin
50-81-7	CAS Registry Number	KEGG COMPOUND
50-81-7	CAS Registry Number	NIST Chemistry WebBook
50-81-7	CAS Registry Number	ChemIDplus
84272	Reaxys Registry Number	Reaxys

Citations	Types	Sources
10799361	PubMed citation	Europe PMC
12180551	PubMed citation	Europe PMC
12569111	PubMed citation	Europe PMC
15917019	PubMed citation	Europe PMC
15925292	PubMed citation	Europe PMC
15949874	PubMed citation	Europe PMC
16425787	PubMed citation	Europe PMC
16522902	PubMed citation	Europe PMC
16611389	PubMed citation	Europe PMC
16725131	PubMed citation	Europe PMC
17253561	PubMed citation	Europe PMC
17623524	PubMed citation	Europe PMC
17636648	PubMed citation	Europe PMC
18813862	PubMed citation	Europe PMC
19273781	PubMed citation	Europe PMC
19580823	PubMed citation	Europe PMC
19692922	PubMed citation	Europe PMC
22770225	PubMed citation	Europe PMC
3015170	PubMed citation	Europe PMC
491997	PubMed citation	Europe PMC
5477017	PubMed citation	Europe PMC
7711198	PubMed citation	Europe PMC
8467348	PubMed citation	Europe PMC
8726814	PubMed citation	Europe PMC
9506998	PubMed citation	Europe PMC

Last Modified

22 January 2024

General Comment

2011-03-23

An essential nutrient and antioxidant with possible anticancer role, especially with intravenous administration. A cofactor in several enzymatic reactions of living organisms, it is linked with effective wound healing and prevention or treatment of scurvy and gout. Also known as vitamin C, it is believed to boost the immune system. Humans alone of the primates require exogenous sources of daily vitamin C.

CHEBI:29073 - L-ascorbic acid

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