Milk Composition Database: Showing metabocard for Folic acid (BMDB0000121)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:48 UTC

Update Date

2020-06-04 20:44:09 UTC

MCDB ID

BMDB0000121

Secondary Accession Numbers

BMDB00121

Metabolite Identification

Common Name

Folic acid

Description

Folic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₉H₁₉N₇O₆

Average Molecular Weight

441.3975

Monoisotopic Molecular Weight

441.139681375

IUPAC Name

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

Traditional Name

folate

CAS Registry Number

59-30-3

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 Key

OVBPIULPVIDEAO-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.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0016 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2249100000-5ad16461f6638538ea08	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-4205390000-4152e24c68306bfe6554	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0000900000-4208ea3c2f5d9026c19f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-0050900000-2c8ad037dc3b270765c4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-0090300000-ebdec84cbb7fe5afbc0b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0007-0903600000-e5d91e4f2ab79d130b76	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-0960000000-108d96993dc78f1e4b61	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0007-0903600000-e5d91e4f2ab79d130b76	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-0960000000-108d96993dc78f1e4b61	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-9e9a33bc590d0f801929	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0aba-6940000000-f0b6076af9cb59413656	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0005-0090600010-5ef6e95b870cc0ebfeb8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0190000000-2d1f624dc1d2d929527f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-015c-9700000000-5a0aeec6b1c2bfddfdf1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-b750c262ac740994e33a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0005-0090600000-c0e3753ba3591c41d1db	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-001i-3900000000-4d5187e4336ce6be5eb7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-0910000000-b3bc3e8ccbba45c85e78	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000010-2c53d9aa251e75638183	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-7370828adb963cbb9246	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0000900000-3b979cd5ecd30ae0d2bf	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00bd-0544900000-aa9a130e2cf3dacfb954	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0954100000-7be7eac442233b5d3bcf	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1960000000-1950169762886f41b6ec	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0114900000-bff7f5f3d20dcd6a4494	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-1249300000-e322ba8675bb922877a9	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9652000000-8c87fa7172ed19a7eb27	2016-09-14	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9410000000-7cba521e870757539424	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.174 uM	Int. Dairy Journa...	details
Detected and Quantified	0.113 uM	NRC. 1989. Recomm...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.136 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.136 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.261 uM	Fooddata+, T...	details
Detected and Quantified	0.261 uM	Fooddata+, T...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.136 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.109 uM	Fooddata+, T...	details
Detected and Quantified	0.132 uM	Fooddata+, T...	details
Detected and Quantified	0.109 uM	Fooddata+, T...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.113 uM	USDA Food Co...	details
Detected and Quantified	0.249 uM	Fooddata+, T...	details
Detected and Quantified	0.249 uM	Fooddata+, T...	details
Detected and Quantified	0.249 uM	Fooddata+, T...	details
Detected and Quantified	0.113 uM	Park, Y. W; Juáre...	details
Detected and Quantified	0.087 +/- 0.004 uM	PMID: 30994344	details
Detected and Quantified	0.083 +/- 0.001 uM	PMID: 30994344	details
Detected and Quantified	0.09 +/- 0.01 uM	PMID: 30994344	details
Detected and Quantified	0.09 +/- 0.01 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000121

DrugBank ID

DB00158

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27470

References

Synthesis Reference

Piper, 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)

Download (PDF)

General References

Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
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.
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.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Folic acid (BMDB0000121)

Structure for BMDB0000121 (Folic acid)