| Common Name |
Pteroyl-D-glutamic acid
| Description |
The active metabolite of Folic acid, is used principally as its calcium salt as an antidote to folic acid antagonists which block the conversion of folic acid to folinic acid. 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 resliting from a deficiency in folic acid. A member of the vitamin B family that stimliates 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 is used in the treatment and prevention of folate deficiencies and megaloblastic anemia.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
Antianemia factorHMDB
apo-FolicHMDB
LeucovorinHMDB
Mission prenatalHMDB
MittafolHMDB
MVC PlusHMDB
N-Pteroyl-D-glutamic acidHMDB
N-[4-[[(2-amino-5-Formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-D-glutamic acidHMDB
NifolinHMDB
novo-FolacidHMDB
NovofolacidHMDB
PteroylmonoglutamateHMDB
Vitamin b11HMDB
VitapedHMDB
| Chemical Formlia |
C20H23N7O7
| Average Molecliar Weight |
473.4393
| Monoisotopic Molecliar Weight |
473.165896125
| IUPAC Name |
(2R)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
| Traditional Name |
Pga
| CAS Registry Number |
54353-24-1
| SMILES |
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@H](CCC(O)=O)C(O)=O)N2C=O)N1
| InChI Identifier |
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m1/s1
| InChI Key |
VVIAGPKUTFNRDU-ZGTCLIOFSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Pteridines and derivatives
| Direct Parent |
Tetrahydrofolic acids
| Alternative Parents |
Glutamic acid and derivatives
Hippuric acids
N-acyl-alpha amino acids
Aminobenzamides
Aniline and substituted anilines
Benzoyl derivatives
Phenylalkylamines
Secondary alkylarylamines
Aminopyrimidines and derivatives
Pyrimidones
Dicarboxylic acids and derivatives
Primary aromatic amines
Heteroaromatic compounds
Tertiary carboxylic acid amides
Vinylogous amides
Secondary carboxylic acid amides
Amino acids
Carboxylic acids
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Tetrahydrofolic acid
Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Aminopyrimidine
Secondary aliphatic/aromatic amine
Pyrimidone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Primary aromatic amine
Benzenoid
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Amino acid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Azacycle
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Enzyme cofactor
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.3 mg/mLALOGPS
logP-1.1ALOGPS
logP-3.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)2.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.46 m3·mol-1ChemAxon
Polarizability46.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Predicted Concentrations |
|
| Biofluid |
Original age |
Original condition |
Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022864
| KNApSAcK ID |
Not Available
| Chemspider ID |
49292
| KEGG Compound ID |
D01211
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Pteroylmonoglutamate
| NuGOwiki Link |
HMDB02140
| Metagene Link |
HMDB02140
| METLIN ID |
6507
| PubChem Compound |
54575
| PDB ID |
Not Available
| ChEBI ID |
474191
Product: BQU57
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 15821037