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Session ID: e6cc802167a1f3fd168b0ba4c54fcda6

Search Type: metabolite

Started at: 2010-02-14 03:49:24

Finished at: 2010-02-14 03:50:55

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Field Result Source
Name
folic acid External
HMDB ID
HMDB00121 HMDB
Bigg ID
Not Available Not Applicable
Description
A member of the vitamin B family that stimulates the hematopoietic system. It is present in the liver and kidney and is found in mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid, being biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by dihydrofolate reductase. These folic acid congeners are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylated tRNA, and generate and use formate. Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia. HMDB
An estimated 13,500 deaths occur annually due to folate deficiency's effect on coronary artery disease and the risk of ischemic heart disease and stroke has been reduced by 15% since folate fortification regulations were enforced. Adequate concentrations of folate, vitamin B12, or vitamin B6 may decrease the circulating level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce risk of heart disease. The NORVIT trial suggests that folic acid supplementation may do more harm than good. Wikipedia
As of 2006, studies have shown that giving folic acid to reduce levels of homocysteine does not result in clinical benefit. One of these studies suggests that folic acid in combination with B12 may even increase some cardiovascular risks. Wikipedia
Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. The antifolate methotrexate is a drug often used to treat cancer because it inhibits the production of the active form of THF from the inactive dihydrofolate (DHF). Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. Also, bone marrow depression (inducing leukopenia and thrombocytopenia), acute renal and hepatic failure have been reported. Wikipedia
Folic acid appears to reduce the risk of stroke. The reviews indicate only that in some individuals the risk of stroke appears to be reduced, but a definite recommendation regarding supplementation beyond the current recommended daily allowance has not been established for stroke prevention. Observed stroke reduction is consistent with the reduction in pulse pressure produced by folate supplementation of 5 mg per day, since hypertension is a key risk factor for stroke. Folic supplements are inexpensive and relatively safe to use and that is why stroke or hyperhomocysteinemia patients are encouraged to consume daily B vitamins including folid acid. Wikipedia
Folic acid food fortification became mandatory in Canada in 1998, with the fortification of 150 µg of folic acid per 100 grams of enriched flour and uncooked cereal grains. The purpose of fortification was to decrease the risk of neural tube defects in newborns. It is important to fortify grains because it is a widely eaten food and the neural tube closes in the first four weeks of gestation, often before many women even know they are pregnant. Canada's fortification program has been successful with a decrease of neural tube defects by 19% since its introduction. A 7 province study from 1993 to 2002 showed a reduction of 46% in the overall rate of neural tube defects after folic acid fortification was introduced in Canada. The fortification program was estimated to raise a person’s folic acid intake level by 70-130 ug/day, however an increase of almost double that amount was actually observed. This could be from the fact that many foods are over fortified by 160-175% the predicted value. In addition, much of the elder population take supplements which adds 400 µg to their daily folic acid intake. This is a concern because 70-80% of the population have detectable levels of unmetabolized folic acid in their blood and high intakes can accelerate the growth of preneoplasmic lesions. It is still unknown the amount of folic acid supplementation that might cause harm,. However, if Canada is going to continue fortifying the food supply they may want to consider decreasing the amount in foods and supplements from 400 ug to 100 or 50 ug. Wikipedia
Folic acid is an important nutrient for women who may become pregnant, because a woman's blood levels of folate fall during pregnancy due to an increased maternal RBC synthesis in the first half of the pregnancy and fetal demands in the second half. The first four weeks of pregnancy (when most women do not even realize they are pregnant) require folic acid for proper development of the brain, skull, and spinal cord. Serious birth defects like neural tube defects are less likely to occur when women take 0.4 mg of folic acid daily. Adequate folate intake during the periconceptional period, the time right before and just after a woman becomes pregnant, helps protect against a number of congenital malformations including neural tube defects (which are the most notable birth defects that occur from folate deficiency). Neural tube defects (NTDs) result in malformations of the spine (spina bifida), skull, and brain (anencephaly). The risk of neural tube defects is significantly reduced when supplemental folic acid is consumed in addition to a healthy diet prior to and during the first month following conception. The protective effect of folate during pregnancy goes beyond NTDs. Supplementation with folic acid has been shown to reduce the risk of congenital heart defects, cleft lip, limb defects, and urinary tract anomalies. Women who could become pregnant are advised to eat foods fortified with folic acid or take supplements in addition to eating folate-rich foods to reduce the risk of some serious birth defects. Having enough folic acid supplements in the months before pregnancy is very important to prevent neural tube defects. Taking 400 micrograms of synthetic folic acid daily from fortified foods and/or supplements has been suggested. The RDA for folate equivalents for pregnant women is 600-800 micrograms, twice the normal RDA of 400 micrograms for women who are not pregnant. Wikipedia
Folic acid supplements prevent mistakes from occurring during DNA replication and repair, for example the mistake of inserting uracils into the DNA. This is a proposed mechanism for folic acid's protection against colorectal cancer. Wikipedia
Folic acid used in fortified foods is a synthetic form called pteroylmonoglutamate. It is in its oxidized state and contains only one conjugated glutamate residue. Folic acid therefore enters via a different carrier system than naturally occurring folate and this may have different effects on folate binding proteins and its transporters. Folic acid has a higher bioavailability than natural folates and are rapidly absorbed across the intestine, therefore it is important to consider the Dietary Folate Equivalent (DFE) when calculating your intake. Natural occurring folate is equal to 1 DFE, however 0.6 µg of folic acid is equal to 1 DFE. Wikipedia
Folic acid, a water-soluble B-complex vitamin, is found in foods such as liver, kidneys, yeast, and leafy, green vegetables. Folic acid is used to diagnose folate deficiency and to treat topical sprue and megaloblastic and macrocytic anemias, hematologic complications resulting from a deficiency in folic acid. DrugBank
Folinic acid, under the drug name leucovorin, is a form of folate (formyl-THF) that can help "rescue" or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. The supplement of folinic acid in patients undergoing methotrexate treatment is to give non rapidly dividing cells enough folate to maintain normal cell functions. The amount of folate given will be depleted by rapidly dividing cells (cancer) very fast and so will not negate the effects of methotrexate. Low dose methotrexate is used to treat a wide variety of non-cancerous diseases such as rheumatoid arthritis, lupus, scleroderma, psoriasis, asthma, sarcoidosis, primary biliary cirrhosis, polymyositis, and inflammatory bowel disease. Low doses of methotrexate can deplete folate stores and cause side effects that are similar to folate deficiency. Both high folate diets and supplemental folic acid may help reduce the toxic side effects of low dose methotrexate without decreasing its effectiveness. Anyone taking low dose methotrexate for the health problems listed above should consult with a physician about the need for a folic acid supplement. Wikipedia
Hyperhomocysteinemia is a predictor of cardiovascular disease and hypertension among children and folic acid is a safe and effective supplement because it reduces serum homocysteine levels as well as systolic and diastolic blood pressure, thus preventing cardiovascular disease in children. Wikipedia
In the form of a series of tetrahydrofolate (THF) compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2′-deoxythymidine-5′-phosphate) from dUMP (2′-deoxyuridine-5′-phosphate). It is a substrate for an important reaction that involves vitamin B12 and it is necessary for the synthesis of DNA, and so required for all dividing cells. Wikipedia
Methylene-THF (CH2FH4) is formed from THF by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate (CH3-THF) can be made from methylene-THF by reduction of the methylene group with NADPH. It is important to note that Vitamin B12 is the only acceptor of methyl-THF. There is also only one acceptor for methyl-B12 which is homocysteine in a reaction catalyzed by homocysteine methyltransferase. This is important because a defect in homocysteine methyltransferase or a deficiency of B12 can lead to a methyl-trap of THF and a subsequent deficiency. Thus, a deficiency in B12 can generate a large pool of methyl-THF that is unable to undergo reactions and will mimic folate deficiency. Another form of THF, formyl-THF or folinic acid) results from oxidation of methylene-THF or is formed from formate donating formyl group to THF. Finally, histidine can donate a single carbon to THF to form methenyl-THF. Wikipedia
Some evidence links a shortage of folate with depression. There is some limited evidence from randomised controlled trials that using folic acid in addition to antidepressants, specifically SSRIs, may have benefits. Research at the University of York and Hull York Medical School has found a link between depression and low levels of folate. One study by the same team involved 15,315 subjects. However, the evidence is probably too limited at present for this to be a routine treatment recommendation. Folic acid supplements have an effect on noradrenaline and serotonine receptors in the brain and this relationship may be the reason why folic acid is an antidepressant. Wikipedia
The pathway leading to the formation of tetrahydrofolate (FH4) begins when folate (F) is reduced to dihydrofolate (DHF) (FH2), which is then reduced to THF. Dihydrofolate reductase catalyses the last step. Vitamin B3 in the form of NADPH is a necessary cofactor for both steps of the synthesis. Wikipedia
The risk of toxicity from folic acid is low because folate is a water soluble vitamin and is regularly removed from the body through urine. The Institute of Medicine has established a tolerable upper intake level (UL) for folate of 1 mg for adult men and women, and a UL of 800 µg for pregnant and lactating (breast-feeding) women less than 18 years of age. Supplemental folic acid should not exceed the UL to prevent folic acid from masking symptoms of vitamin B12 deficiency. Wikipedia
There is a relationship between folic acid and allergic diseases. In one study that examined the relationship between serum folate levels and markers of atopy, wheeze, and asthma in 8083 subjects serum folate levels were found to be inversely related to IgE level, atopy, and wheeze in a dose-response relationship. Increased folate levels were also associated with decreased risk of doctor-diagnosed asthma. Folic acid supplementation during late pregnancy is associated with an increased risk of childhood asthma, increased risk of persistent asthma, and poorer respiratory function in young children. Wikipedia
While the role in folate as a cancer treatment is well established its long term effectiveness is diminished by cellular response. In response to decreased THF the cell begins to transcribe more DHF reductase, the enzyme that reduces DHF to THF. Because methotrexate is a competitive inhibitor of DHF reductase increased concentrations of DHF reductase can overcome the drugs inhibition. Wikipedia
Chemical Kingdom
Organic BioSpider
Chemical Class
Pterins HMDB
Vitamins NuGO
Chemical Species
aromatic compound Checkmol
carboxylic acid Checkmol
heterocyclic compound Checkmol
oxo(het)arene Checkmol
primary amine Checkmol
primary aromatic amine Checkmol
secondary aliphatic/aromatic amine (alkylarylamine) Checkmol
secondary amine Checkmol
secondary carboxylic acid amide Checkmol
Synonym
6484-89-5 (mono-hydrochloride salt) Pubchem
Acfol (spain) Pubchem
Acide Folique 5 Tab DPD
Acide folique Pubchem
Acide folique [inn-french] Pubchem
Acido folico Pubchem
Acido folico [inn-spanish] Pubchem
Acidum folicum Pubchem
Acidum folicum [inn-latin] Pubchem
Acifolic HMDB
Antianemia factor Pubchem
Apo Folic Acid Tab 5mg DPD
Berocca PN Pubchem
CERNEVIT-12 Pubchem
Cytofol HMDB
DHF Pubchem
Dosfolat b activ HMDB
Euro Folic 5mg DPD
F7876_SIGMA Pubchem
F8758_SIGMA Pubchem
F8890_SIGMA Pubchem
FA Pubchem
FOL Pubchem
Facid NIST
Factor u Pubchem
Folacal DPD
Folacid HMDB
Folacin HMDB
Folaemin Pubchem
Folaemin [netherlands] Pubchem
Folan NIST
Folasic (australia) Pubchem
Folate HMDB
Folbal HMDB
Folcidin HMDB
Folcidin (van) Pubchem
Folcysteine NIST
Foldine HMDB
Foldine [france] Pubchem
Folettes HMDB
Foliamin HMDB
Folic Acid 0.4 Mg Tablet DPD
Folic Acid 0.400mg Tablets Usp DPD
Folic Acid 0.4mg DPD
Folic Acid 0.4mg (400mcg) DPD
Folic Acid 0.4mg Tablets DPD
Folic Acid 0.8mg DPD
Folic Acid 1 Mg DPD
Folic Acid 1 Mg Usp DPD
Folic Acid 1mg DPD
Folic Acid 400 Mcg Tablets DPD
Folic Acid Tab 1mg DPD
Folic Acid Tab 1mg Usp DPD
Folic Acid Tab 25mg DPD
Folic Acid Tab 5mg DPD
Folic Acid Tablets Usp 1mg DPD
Folic acid (JP15/USP/INN) Pubchem
Folic acid (TN) Pubchem
Folic acid [ban:inn:jan] Pubchem
Folic acid [inn:ban:jan] Pubchem
Folic acid dihydrate Pubchem
Folic acid injection usp DPD
Folicet HMDB
Folicet (TN) Pubchem
Folico Pubchem
Folico (italy) Pubchem
Folina Pubchem
Folina (italy) Pubchem
Folipac HMDB
Folsaeure Pubchem
Folsan HMDB
Folsaure HMDB
Folsav HMDB
Foluite NIST
Folvite HMDB
Folvron Pubchem
Glutamic acid, pteroyl-, l- NIST
Incafolic HMDB
Infuvite pediatric Pubchem
Kyselina listova NIST
Kyselina listova [czech] Pubchem
L-pteroylglutamic acid NIST
Liver lactobacillus casei factor HMDB
Liver lactobacillus, casei factor NIST
M.V.I.-12 LYOPHILIZED Pubchem
M.v.I. pediatric Pubchem
MULTI-12 Pubchem
MVC plus Pubchem
Millafol HMDB
Mission prenatal NIST
Mittafol Pubchem
Mixture name Pubchem
N-pteroyl-l-glutamic acid HMDB
Nifolin Pubchem
Nifolin [denmark] Pubchem
Novo-Folacid 5mg DPD
Novofolacid Pubchem
Novofolacid [canada] Pubchem
PGA HMDB
Pga (van) Pubchem
Prestwick_230 Pubchem
Pteglu HMDB
Pteroyl-l-glutamate HMDB
Pteroyl-l-glutamic acid HMDB
Pteroyl-l-monoglutamate HMDB
Pteroyl-l-monoglutamic acid HMDB
Pteroylglutamate HMDB
Pteroylglutamic acid HMDB
Pteroylmonoglutamate Pubchem
Pteroylmonoglutamic acid HMDB
Serum folate level Pubchem
THG Pubchem
UNII-935E97BOY8 Pubchem
USAF cb-13 NIST
Vitamin B11 NIST
Vitamin B9 Pubchem
Vitamin BC HMDB
Vitamin b NIST
Vitamin be HMDB
Vitamin m HMDB
Vitaped Pubchem
nchembio.108-comp10 Pubchem
CAS
59-30-3 HMDB
InChI Identifier
InChI=1/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)
World Wide Molecular Matrix
IUPAC
2-[[4-[(2-amino-4-hydroxy-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid HMDB
Chemical Formula
C19H19N7O6 HMDB
Chemical Structure
Chemical Structure HMDB
Average Molecular Weight (g/mol)
441.397460 BioSpider
Monoisotopic Molecular Weight (g/mol)
441.139680 BioSpider
SMILES (Isomeric)
O=C(O)C(NC(=O)c1ccc(cc1)NCc2nc3c(nc2)N/C(=N\C3=O)N)CCC(=O)O
ChemSpider
SMILES (Canonical)
NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)=CN=C2N1
HMDB
Kegg Compound
C00504 HMDB
Pubchem Compound ID
6037 HMDB
Pubchem Substance ID
10318222 Pubchem
10321330 Pubchem
11112150 Pubchem
11335669 Pubchem
11360908 Pubchem
11364275 Pubchem
11366837 Pubchem
11369399 Pubchem
11371658 Pubchem
11375360 Pubchem
11377561 Pubchem
11461880 Pubchem
11485093 Pubchem
11489275 Pubchem
11490565 Pubchem
11493565 Pubchem
11495195 Pubchem
11537760 Pubchem
14857129 Pubchem
148901 Pubchem
14930521 Pubchem
16028504 Pubchem
16077361 Pubchem
22389272 Pubchem
24845192 Pubchem
24894950 Pubchem
24894973 Pubchem
24894977 Pubchem
24894979 Pubchem
26486597 Pubchem
26612259 Pubchem
26680757 Pubchem
26704619 Pubchem
26704771 Pubchem
26708391 Pubchem
26710566 Pubchem
26710571 Pubchem
26710897 Pubchem
26710911 Pubchem
26710913 Pubchem
26719334 Pubchem
26754169 Pubchem
29204143 Pubchem
29225051 Pubchem
3787 Kegg
46394037 Pubchem
46508092 Pubchem
47184484 Pubchem
47291092 Pubchem
47440205 Pubchem
47515277 Pubchem
47959695 Pubchem
48184954 Pubchem
48259189 Pubchem
48334445 Pubchem
48416033 Pubchem
48422025 Pubchem
48423436 Pubchem
49698592 Pubchem
49755686 Pubchem
49856246 Pubchem
50085945 Pubchem
50100133 Pubchem
50130693 Pubchem
50412567 Pubchem
56310593 Pubchem
56313228 Pubchem
56313229 Pubchem
56320918 Pubchem
56435724 Pubchem
56435752 Pubchem
57323136 Pubchem
57654192 Pubchem
584223 Pubchem
7847138 Pubchem
7887399 Pubchem
7887539 Pubchem
7979297 Pubchem
8144505 Pubchem
8149795 Pubchem
8153763 Pubchem
829572 Pubchem
831381 Pubchem
831592 Pubchem
831633 Pubchem
831664 Pubchem
834516 Pubchem
835597 Pubchem
835744 Pubchem
837196 Pubchem
841329 Pubchem
84943783 Pubchem
85165103 Pubchem
85354204 Pubchem
85741522 Pubchem
85741526 Pubchem
87225846 Pubchem
87275284 Pubchem
OMIM ID
136610 HMDB
136630 HMDB
229050 HMDB
229100 HMDB
236200 HMDB
236250 HMDB
309548 HMDB
601634 HMDB
601775 HMDB
603174 HMDB
608866 HMDB
ChEBI
27470 HMDB
BioCyc
FOLATE HMDB
Wikipedia
Folic acid HMDB
Melting Point
250 oC HMDB
Charge
Not Available Not Applicable
State
Solid HMDB
MSDS Link
1266144637.pdf www.sciencelab.com
1266144639.pdf HMDB
Experimental Water Solubility
0.0016 mg/mL at 25 oC [MERCK INDEX (1983)] PhysProp
Predicted Water Solubility
0.186 mg/mL [Predicted by ALOGPS] Alogps
Experimental LogP
Not Available Not Applicable
Predicted LogP
-0.66 [Predicted by ALOGPS] Alogps
-2.81 [MEYLAN,WM & HOWARD,PH (1995)] HMDB
pKa
1 st : 2.3, 2 nd : 8.3 Wikipedia
SDF File
1266144583.sdf Pubchem
Mol File
1266144622.mol Molconvert
Pdb File
1266144626.pdb Molconvert
Mass Spec File
Not Available Not Applicable
Associated Disorder
Not Available Not Applicable
Pathway
Not Available Not Applicable
Enzymes
O60779
[ UniProt | Analyze ]
HMDB
O95954
[ UniProt | Analyze ]
HMDB
P00374
[ UniProt | Analyze ]
HMDB
P14207
[ UniProt | Analyze ]
HMDB
P15328
[ UniProt | Analyze ]
HMDB
P41439
[ UniProt | Analyze ]
HMDB
P41440
[ UniProt | Analyze ]
HMDB
P49914
[ UniProt | Analyze ]
HMDB
Q14749
[ UniProt | Analyze ]
HMDB
Q53S99
[ UniProt | Analyze ]
HMDB
Q9H2D1
[ UniProt | Analyze ]
HMDB
Compartments
Not Available Not Applicable
Reaction (query compound consumed)
Not Available Not Applicable
Reaction (query compound produced)
Not Available Not Applicable
Reaction, reversible (query compound neither consumed nor produced)
Not Available Not Applicable
Reaction (query compound is transported across a membrane)
Not Available Not Applicable