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Folic acid (FDB014504)

Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2019-11-26 03:10:13 UTC
Primary IDFDB014504
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFolic acid
DescriptionFolic 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 Number59-30-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP-0.04ALOGPS
logP-0.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area208.99 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.01 m³·mol⁻¹ChemAxon
Polarizability42.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H19N7O6
IUPAC name(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
InChI IdentifierInChI=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 KeyOVBPIULPVIDEAO-LBPRGKRZSA-N
Isomeric SMILESNC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1
Average Molecular Weight441.3975
Monoisotopic Molecular Weight441.139681375
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 51.70%; H 4.34%; N 22.21%; O 21.75%DFC
Melting Point250 oC
Boiling PointNot Available
Experimental Water Solubility0.0016 mg/mL at 25 oCMERCK INDEX (1983)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +23 (c, 0.5 in 1M NaOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9410000000-7cba521e8707575394242014-09-20View Spectrum
Predicted GC-MSFolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-2249100000-5ad16461f6638538ea08Spectrum
Predicted GC-MSFolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-4205390000-4152e24c68306bfe6554Spectrum
Predicted GC-MSFolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFolic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0000900000-4208ea3c2f5d9026c19f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-0050900000-2c8ad037dc3b270765c42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-0090300000-ebdec84cbb7fe5afbc0b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0007-0903600000-e5d91e4f2ab79d130b762012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-002b-0960000000-108d96993dc78f1e4b612017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0007-0903600000-e5d91e4f2ab79d130b762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-0960000000-108d96993dc78f1e4b612017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-9e9a33bc590d0f8019292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-6940000000-f0b6076af9cb594136562021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0005-0090600010-5ef6e95b870cc0ebfeb82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0190000000-2d1f624dc1d2d929527f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-015c-9700000000-5a0aeec6b1c2bfddfdf12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b750c262ac740994e33a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0005-0090600000-c0e3753ba3591c41d1db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-001i-3900000000-4d5187e4336ce6be5eb72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0910000000-b3bc3e8ccbba45c85e782021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000010-2c53d9aa251e756381832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-7370828adb963cbb92462021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-3b979cd5ecd30ae0d2bf2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00bd-0544900000-aa9a130e2cf3dacfb9542016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0954100000-7be7eac442233b5d3bcf2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1960000000-1950169762886f41b6ec2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0114900000-bff7f5f3d20dcd6a44942016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r7-1249300000-e322ba8675bb922877a92016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9652000000-8c87fa7172ed19a7eb272016-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID5815
ChEMBL IDCHEMBL1622
KEGG Compound IDC00504
Pubchem Compound ID6037
Pubchem Substance IDNot Available
ChEBI ID27470
Phenol-Explorer IDNot Available
DrugBank IDDB00158
HMDB IDHMDB00121
CRC / DFC (Dictionary of Food Compounds) IDJRL93-O:JRL93-O
EAFUS ID1396
Dr. Duke IDFOLIC-ACID|FOLACIN|FOLATE
BIGG ID35180
KNApSAcK IDC00001539
HET IDFOL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1098971
SuperScent IDNot Available
Wikipedia IDFolic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti anemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cervicaldysplasic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cheiliticDUKE
anti coronary52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti glossiticDUKE
anti gout52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti infertility52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti metaplasticDUKE
anti myelotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti neuropathicDUKE
anti periodontalDUKE
anti periodontiticDUKE
anti plaqueDUKE
anti polypDUKE
anti psychotic35476 Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.DUKE
anti spina-bifida52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hematopoieticDUKE
immunostimulant50847 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
uricosuricDUKE
xanthine oxidase inhibitor35634 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
NameGene NameUniProt ID
Formimidoyltransferase-cyclodeaminaseFTCDO95954
Thiamine transporter 1SLC19A2O60779
Dihydrofolate reductaseDHFRP00374
Folate receptor alphaFOLR1P15328
Folate transporter 1SLC19A1P41440
Folate receptor gammaFOLR3P41439
Gamma-glutamyl hydrolaseGGHQ92820
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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.