Showing Compound Folic acid (FDB014504)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2019-11-26 03:10:13 UTC

Primary ID

FDB014504

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Folic acid

Description

Folic acid, also known as folate or folsaeure, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Folic acid is a moderately basic compound (based on its pKa). Folic acid exists in all living species, ranging from bacteria to humans. Folic acid is a potentially toxic compound. Folic acid, with regard to humans, has been found to be associated with several diseases such as fibromyalgia, hereditary folate malabsorption, bladder infections, and alzheimer's disease; folic acid has also been linked to the inborn metabolic disorder folate deficiency.

CAS Number

59-30-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Folate	ChEBI
Folsaeure	ChEBI
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid	ChEBI
N-Pteroyl-L-glutamic acid	ChEBI
PGA	ChEBI
PteGlu	ChEBI
Pteroyl-L-glutamic acid	ChEBI
Pteroyl-L-monoglutamic acid	ChEBI
Pteroylglutamic acid	ChEBI
Vitamin BC	ChEBI
Vitamin m	ChEBI
Folicet	Kegg
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamate	Generator
N-Pteroyl-L-glutamate	Generator
Pteroyl-L-glutamate	Generator
Pteroyl-L-monoglutamate	Generator
Pteroylglutamate	Generator
Acifolic	HMDB
Cytofol	HMDB
Dosfolat b activ	HMDB
Folacid	HMDB
Folacin	HMDB
Folbal	HMDB
Folcidin	HMDB
Foldine	HMDB
Folettes	HMDB
Foliamin	HMDB
Folipac	HMDB
Folsan	HMDB
Folsaure	HMDB
Folsav	HMDB
Folvite	HMDB
Incafolic	HMDB
Liver lactobacillus casei factor	HMDB
Millafol	HMDB
N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid	HMDB
N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
Pteroylmonoglutamic acid	HMDB
Vitamin be	HMDB
Folic acid, (DL)-isomer	HMDB
Folic acid, sodium salt	HMDB
Folic acid, (D)-isomer	HMDB
Folic acid, monosodium salt	HMDB
Folic acid, potassium salt	HMDB
b9, Vitamin	HMDB
Folic acid, calcium salt (1:1)	HMDB
Folic acid, monopotassium salt	HMDB
Vitamin b9	HMDB
Citrovorin	db_source
Coenzyme F	db_source
Factor u	biospider
Folcysteine	biospider
Folic acid	biospider
Foluite	biospider
Folvron	biospider
Leucal	db_source
Mittafol	biospider
N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]glutamic acid, 9CI	db_source
N-[4-[[(2-amino-3,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
Pteroylmonoglutamate	biospider
Vitamin b	biospider
Vitamin B11	biospider
Vitamin B9	biospider
Vitamin Bc	db_source
Vitamin M	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.076 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	-0.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	2.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	208.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.01 m³·mol⁻¹	ChemAxon
Polarizability	42.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C19H19N7O6

IUPAC name

(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

InChI Identifier

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

InChI Key

OVBPIULPVIDEAO-LBPRGKRZSA-N

Isomeric SMILES

NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1

Average Molecular Weight

441.3975

Monoisotopic Molecular Weight

441.139681375

Classification

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:545959 )
phenols (CHEBI:545959 )
monomethoxybenzene (CHEBI:545959 )

Ontology

Physiological effect

Health effect:

Health condition:

Folate deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Parenteral:

Intravenous

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Microbe:

Plant:

Biological location:

Organ and components:

Cell and elements:

Extracellular

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Rheumatoid arthritis

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Essential vitamin

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 51.70%; H 4.34%; N 22.21%; O 21.75%	DFC
Melting Point	250 oC
Boiling Point	Not Available
Experimental Water Solubility	0.0016 mg/mL at 25 oC	MERCK INDEX (1983)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +23 (c, 0.5 in 1M NaOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9410000000-7cba521e870757539424	2014-09-20	View Spectrum
Predicted GC-MS	Folic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-2249100000-5ad16461f6638538ea08	Spectrum
Predicted GC-MS	Folic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-4205390000-4152e24c68306bfe6554	Spectrum
Predicted GC-MS	Folic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Folic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0000900000-4208ea3c2f5d9026c19f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-0050900000-2c8ad037dc3b270765c4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-0090300000-ebdec84cbb7fe5afbc0b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0007-0903600000-e5d91e4f2ab79d130b76	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-0960000000-108d96993dc78f1e4b61	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0007-0903600000-e5d91e4f2ab79d130b76	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-0960000000-108d96993dc78f1e4b61	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-9e9a33bc590d0f801929	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0aba-6940000000-f0b6076af9cb59413656	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0005-0090600010-5ef6e95b870cc0ebfeb8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0190000000-2d1f624dc1d2d929527f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-015c-9700000000-5a0aeec6b1c2bfddfdf1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-b750c262ac740994e33a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0005-0090600000-c0e3753ba3591c41d1db	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-001i-3900000000-4d5187e4336ce6be5eb7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-0910000000-b3bc3e8ccbba45c85e78	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000010-2c53d9aa251e75638183	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-7370828adb963cbb9246	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0000900000-3b979cd5ecd30ae0d2bf	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00bd-0544900000-aa9a130e2cf3dacfb954	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0954100000-7be7eac442233b5d3bcf	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1960000000-1950169762886f41b6ec	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0114900000-bff7f5f3d20dcd6a4494	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-1249300000-e322ba8675bb922877a9	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9652000000-8c87fa7172ed19a7eb27	2016-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27470

Phenol-Explorer ID

Not Available

DrugBank ID

DB00158

HMDB ID

HMDB00121

CRC / DFC (Dictionary of Food Compounds) ID

JRL93-O:JRL93-O

EAFUS ID

1396

Dr. Duke ID

FOLIC-ACID|FOLACIN|FOLATE

BIGG ID

35180

KNApSAcK ID

C00001539

HET ID

FOL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1098971

SuperScent ID

Not Available

Wikipedia ID

Folic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti anemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cervicaldysplasic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cheilitic			DUKE
anti coronary	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dementia	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti glossitic			DUKE
anti gout	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti infertility	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti metaplastic			DUKE
anti myelotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti neuropathic			DUKE
anti periodontal			DUKE
anti periodontitic			DUKE
anti plaque			DUKE
anti polyp			DUKE
anti psychotic	35476	Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.	DUKE
anti spina-bifida	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
hematopoietic			DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
uricosuric			DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE

Enzymes

Name	Gene Name	UniProt ID
Formimidoyltransferase-cyclodeaminase	FTCD	O95954
Thiamine transporter 1	SLC19A2	O60779
Dihydrofolate reductase	DHFR	P00374
Folate receptor alpha	FOLR1	P15328
Folate transporter 1	SLC19A1	P41440
Folate receptor gamma	FOLR3	P41439
Gamma-glutamyl hydrolase	GGH	Q92820

Pathways

Name	SMPDB Link	KEGG Link
Folate Metabolism	SMP00053	map00670
Pterine Biosynthesis	SMP00005	map00790

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.