folic acid (CHEBI:27470)

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CHEBI:27470 - folic acid

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ChEBI Name	folic acid

ChEBI ID	CHEBI:27470

Definition	An N-acyl-amino acid that is a form of the water-soluble vitamin B₉. Its biologically active forms (tetrahydrofolate and others) are essential for nucleotide biosynthesis and homocysteine remethylation.

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

Secondary ChEBI IDs	CHEBI:42610, CHEBI:5140, CHEBI:569217, CHEBI:24075

Supplier Information	ChemicalBook:CB5100903, eMolecules:36758208, eMolecules:474902, eMolecules:5748014, eMolecules:884420, ZINC000008577218

Download	Molfile XML SDF

more structures >>

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M END): 17 ms

reading 51 atoms

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Wikipedia	License
Folate, also known as vitamin B9 and folacin, is one of the B vitamins. Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and storage. Folate is required for the body to make DNA and RNA and metabolise amino acids necessary for cell division and maturation of blood cells. As the human body cannot make folate, it is required in the diet, making it an essential nutrient. It occurs naturally in many foods. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements. Folate in the form of folic acid is used to treat anemia caused by folate deficiency. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby. NTDs include anencephaly and spina bifida, among other defects. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs. More than 80 countries use either mandatory or voluntary fortification of certain foods with folic acid as a measure to decrease the rate of NTDs. Long-term supplementation with relatively large amounts of folic acid is associated with a small reduction in the risk of stroke and an increased risk of prostate cancer. There are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency. Not consuming enough folate can lead to folate deficiency. This may result in a type of anemia in which red blood cells become abnormally large. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Folate deficiency in children may develop within a month of poor dietary intake. In adults, normal total body folate is between 10 and 30 mg with about half of this amount stored in the liver and the remainder in blood and body tissues. In plasma, the natural folate range is 150 to 450 nM. Folate was discovered between 1931 and 1943. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions. The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables.
Read full article at Wikipedia

Formula

C19H19N7O6

Net Charge

Average Mass

441.39750

Monoisotopic Mass

441.13968

InChI

InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1

InChIKey

OVBPIULPVIDEAO-LBPRGKRZSA-N

SMILES

Nc1nc2ncc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)nc2c(=O)[nH]1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Arabidopsis thaliana (NCBI:txid3702)	Found in cell suspension culture (BTO:0000221). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708)	Found in leaf lamina (BTO:0000719). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708)	From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708)	From MetaboLights See: MetaboLights Study
Micromonas pusilla (NCBI:txid38833)	From MetaboLights See: MetaboLights Study
Trypanosoma brucei (NCBI:txid5691)	From MetaboLights See: MetaboLights Study
Ruegeria pomeroyi (NCBI:txid89184)	Found in endometabolome From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in cytoplasm (GO:0005737). See: Geigy Scientific Tables, 8th Rev edition, pp. 131. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). nutrient A nutrient is a food component that an organism uses to survive and grow. 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 B vitamin )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	folic acid (CHEBI:27470) has functional parent pteroic acid (CHEBI:38794) folic acid (CHEBI:27470) has role human metabolite (CHEBI:77746) folic acid (CHEBI:27470) has role mouse metabolite (CHEBI:75771) folic acid (CHEBI:27470) has role nutrient (CHEBI:33284) folic acid (CHEBI:27470) is a N-acyl-amino acid (CHEBI:51569) folic acid (CHEBI:27470) is a folic acids (CHEBI:37445) folic acid (CHEBI:27470) is conjugate acid of folate(2−) (CHEBI:62501)

Incoming	4-aminofolic acid (CHEBI:22526) has functional parent folic acid (CHEBI:27470) vitamin B complex (CHEBI:75782) has part folic acid (CHEBI:27470) folate(2−) (CHEBI:62501) is conjugate base of folic acid (CHEBI:27470)

IUPAC Name

N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid

INNs	Sources
acide folique	WHO MedNet
ácido fólico	WHO MedNet
acidum folicum	WHO MedNet
folic acid	WHO MedNet

Synonyms	Sources
(2S)-2-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzamido)pentanedioic acid	IUPAC
Folate	KEGG COMPOUND
Folsäure	ChEBI
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid	PDBeChem
N-pteroyl-L-glutamic acid	ChEBI
PGA	NIST Chemistry WebBook
PteGlu	NIST Chemistry WebBook
pteroyl-L-glutamic acid	ChemIDplus
pteroyl-L-monoglutamic acid	ChemIDplus
pteroylglutamic acid	KEGG COMPOUND
pteroylmonoglutamic acid	ChemIDplus
vitamin B₁₁	ChemIDplus
vitamin B₉	ChemIDplus
vitamin Bc	ChemIDplus
vitamin Be	ChemIDplus
vitamin M	ChemIDplus

Brand Names	Sources
Acfol	ChemIDplus
Folicet	KEGG DRUG

Manual Xrefs	Databases
1231	DrugCentral
5815	ChemSpider
C00001539	KNApSAcK
C00504	KEGG COMPOUND
CPD-12826	MetaCyc
D00070	KEGG DRUG
DB00158	DrugBank
FDB014504	FooDB
FOL	PDBeChem
Folic_Acid	Wikipedia
HMDB0000121	HMDB
LSM-5355	LINCS
View more database links

Registry Numbers	Types	Sources
100781	Reaxys Registry Number	Reaxys
59-30-3	CAS Registry Number	NIST Chemistry WebBook
59-30-3	CAS Registry Number	ChemIDplus

Citations

Last Modified

23 July 2021

CHEBI:27470 - folic acid

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