Showing metabocard for Folic acid (BMDB0000121)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
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Record Information
Version1.0
Creation Date2016-09-30 22:19:48 UTC
Update Date2020-06-04 20:44:09 UTC
BMDB IDBMDB0000121
Secondary Accession Numbers
  • BMDB00121
Metabolite Identification
Common NameFolic acid
DescriptionFolic acid, also known as folate or vitamin m, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Folic acid is a drug which is used for treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood. Folic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Folic acid exists in all living species, ranging from bacteria to humans. Folic acid participates in a number of enzymatic reactions, within cattle. In particular, Folic acid can be biosynthesized from dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Folic acid can be converted into folic acid; which is catalyzed by the enzyme proton-coupled folate transporter. In cattle, folic acid is involved in the metabolic pathway called the folate metabolism pathway. Folic acid is a potentially toxic compound. Folic acid has been found to be associated with several diseases known as dimethylglycine dehydrogenase deficiency, bladder infections, fibromyalgia, and hereditary folate malabsorption; also folic acid has been linked to the inborn metabolic disorders including folate deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC19H19N7O6
Average Molecular Weight441.3975
Monoisotopic Molecular Weight441.139681375
IUPAC Name(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional Namefolate
CAS Registry Number59-30-3
SMILES
NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1
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 KeyOVBPIULPVIDEAO-LBPRGKRZSA-N
Chemical Taxonomy
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
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2249100000-5ad16461f6638538ea08View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-4205390000-4152e24c68306bfe6554View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0000900000-4208ea3c2f5d9026c19fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-0050900000-2c8ad037dc3b270765c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-0090300000-ebdec84cbb7fe5afbc0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0007-0903600000-e5d91e4f2ab79d130b76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-002b-0960000000-108d96993dc78f1e4b61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0007-0903600000-e5d91e4f2ab79d130b76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-0960000000-108d96993dc78f1e4b61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-9e9a33bc590d0f801929View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-6940000000-f0b6076af9cb59413656View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0005-0090600010-5ef6e95b870cc0ebfeb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0190000000-2d1f624dc1d2d929527fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-015c-9700000000-5a0aeec6b1c2bfddfdf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b750c262ac740994e33aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0005-0090600000-c0e3753ba3591c41d1dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-001i-3900000000-4d5187e4336ce6be5eb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0910000000-b3bc3e8ccbba45c85e78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000010-2c53d9aa251e75638183View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-7370828adb963cbb9246View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-3b979cd5ecd30ae0d2bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00bd-0544900000-aa9a130e2cf3dacfb954View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0954100000-7be7eac442233b5d3bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1960000000-1950169762886f41b6ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0114900000-bff7f5f3d20dcd6a4494View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r7-1249300000-e322ba8675bb922877a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9652000000-8c87fa7172ed19a7eb27View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9410000000-7cba521e870757539424View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Brain
  • Erythrocyte
  • Kidney
  • Liver
  • Milk
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0000121
DrugBank IDDB00158
Phenol Explorer Compound IDNot Available
FooDB IDFDB014504
KNApSAcK IDC00001539
Chemspider ID5815
KEGG Compound IDC00504
BioCyc IDCPD-12826
BiGG ID35180
Wikipedia LinkFolic_Acid
METLIN ID246
PubChem Compound6037
PDB IDNot Available
ChEBI ID27470
References
Synthesis ReferencePiper, James R.; McCaleb, George S.; Montgomery, John A. Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1H)-pteridinone. Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
  2. NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
  3. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  5. USDA Food Composition Databases [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details
1. Dihydrofolate reductase
General function:
Coenzyme transport and metabolism
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFR2 (By similarity).
Gene Name:
DHFR
Uniprot ID:
P00376
Molecular weight:
21604.0
Reactions
Dihydrofolic acid + NADP → Folic acid + NADPHdetails
Enzyme Details
2. Solute carrier family 19 (Folate transporter), member 1
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A1
Uniprot ID:
Q17QC9
Molecular weight:
56622.0
Enzyme Details
3. SLC19A3 protein
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A3
Uniprot ID:
A7E352
Molecular weight:
54249.0
Enzyme Details
4. Solute carrier family 19 member 1
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A1
Uniprot ID:
Q0V8L3
Molecular weight:
34009.0
Enzyme Details
5. Folate receptor 2 (Fetal)
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
FOLR2
Uniprot ID:
Q0VCN9
Molecular weight:
29333.0
Enzyme Details
6. Folate receptor alpha
General function:
Involved in folic acid binding
Specific function:
Binds to folate and reduced folic acid derivatives and mediates delivery of 5-methyltetrahydrofolate and folate analogs into the interior of cells. Has high affinity for folate and folic acid analogs at neutral pH. Exposure to slightly acidic pH after receptor endocytosis triggers a conformation change that strongly reduces its affinity for folates and mediates their release. Required for normal embryonic development and normal cell proliferation (By similarity).
Gene Name:
FOLR1
Uniprot ID:
P02702
Molecular weight:
27922.0