| Common Name |
5-Methyltetrahydropteroylpentaglutamate
| Description |
5-Methyltetrahydropteroylpentaglutamate is a naturally occurring folate coenzyme; binds to an inhibits glyxine N-methyltransferase to regliate the availability of methyl groups in the liver (Journal of Biological Chemistry 264 (16): 9638-9642 JUN 5 1989 ).
| Structure |
| Synonyms |
| Value |
Source |
5-Me-THF(glu)5HMDB
5-Methyltetrahydropteroylpentaglutamic acidHMDB
| Chemical Formlia |
C40H53N11O18
| Average Molecliar Weight |
975.9117
| Monoisotopic Molecliar Weight |
975.357003947
| IUPAC Name |
(2S,6R,11S)-2,11-diamino-6-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido}-6-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-7-(carboxymethyl)-5,8-dioxododecanedioic acid
| Traditional Name |
(2S,6R,11S)-2,11-diamino-6-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido}-6-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-7-(carboxymethyl)-5,8-dioxododecanedioic acid
| CAS Registry Number |
39555-46-9
| SMILES |
CN1C(CNC2=CC=C(C=C2)C(=O)N(C(=O)CC[C@H](N)C(O)=O)[C@](C(CC(O)=O)C(=O)CC[C@H](N)C(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)OC(=O)CC[C@H](N)C(O)=O)CNC2=C1C(=O)N=C(N)N2
| InChI Identifier |
InChI=1S/C40H53N11O18/c1-50-19(16-47-31-30(50)32(58)49-39(45)48-31)15-46-18-4-2-17(3-5-18)33(59)51(27(54)12-8-23(43)36(64)65)40(26(53)11-7-22(42)35(62)63,38(68)69-29(57)13-9-24(44)37(66)67)20(14-28(55)56)25(52)10-6-21(41)34(60)61/h2-5,19-24,46H,6-16,41-44H2,1H3,(H,55,56)(H,60,61)(H,62,63)(H,64,65)(H,66,67)(H4,45,47,48,49,58)/t19?,20?,21-,22-,23-,24-,40+/m0/s1
| InChI Key |
WNRFVFOPCUPRFK-JPUKBXPDSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) .
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Pteridines and derivatives
| Direct Parent |
Tetrahydrofolic acids and derivatives
| Alternative Parents |
N-epsilon-acyl lysines
Glutamic acid and derivatives
Glutamine and derivatives
Hippuric acids and derivatives
Aminobenzamides
L-alpha-amino acids
Phenylalkylamines
Aniline and substituted anilines
Benzoyl derivatives
Dialkylarylamines
Gamma-keto acids and derivatives
Secondary alkylarylamines
Pyrimidones
Aminopyrimidines and derivatives
Beta-keto acids and derivatives
Amino fatty acids
Primary aromatic amines
N-substituted carboxylic acid imides
N-acyl amines
Gamma-amino ketones
Carboxylic acid anhydrides
Vinylogous amides
Dicarboximides
Heteroaromatic compounds
Amino acids
Carboxylic acids
Azacyclic compounds
Hydrocarbon derivatives
Monoalkylamines
Organic oxides
Organopnictogen compounds
| Substituents |
Tetrahydrofolic acid or derivatives
N-epsilon-acetyl-lysine
Glutamine or derivatives
Glutamic acid or derivatives
Hippuric acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
L-alpha-amino acid
Benzoic acid or derivatives
Gamma-keto acid
Tertiary aliphatic/aromatic amine
Benzoyl
Dialkylarylamine
Aniline or substituted anilines
Phenylalkylamine
Beta-keto acid
Amino fatty acid
Secondary aliphatic/aromatic amine
Pyrimidone
Aminopyrimidine
Monocyclic benzene moiety
N-acyl-amine
Pyrimidine
Primary aromatic amine
Benzenoid
Carboxylic acid imide, n-substituted
Keto acid
Fatty acyl
Gamma-aminoketone
Heteroaromatic compound
Vinylogous amide
Carboxylic acid anhydride
Carboxylic acid imide
Dicarboximide
Ketone
Amino acid
Tertiary amine
Amino acid or derivatives
Secondary amine
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Carbonyl group
Amine
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| 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 Solubility0.47 mg/mLALOGPS
logP-2.8ALOGPS
logP-11ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area500.25 Å2ChemAxon
Rotatable Bond Count29ChemAxon
Refractivity239.65 m3·mol-1ChemAxon
Polarizability92.65 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
| 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 |
FDB022868
| KNApSAcK ID |
Not Available
| Chemspider ID |
168178
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02148
| Metagene Link |
HMDB02148
| METLIN ID |
6511
| PubChem Compound |
193793
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Tranilast (trans-)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Bagley PJ, Selhub J: A common mutation in the methylenetetrahydrofolate reductase gene is associated with an accumulation of formylated tetrahydrofolates in red blood cells. Proc Natl Acad Sci U S A. 1998 Oct 27;95(22):13217-20. [PubMed:9789068 ]
|
PMID: 15280536