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135-16-0 molecular structure
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(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

ChemBase ID: 3
Molecular Formular: C19H23N7O6
Molecular Mass: 445.42922
Monoisotopic Mass: 445.17098149
SMILES and InChIs

SMILES:
O=c1nc([nH]c2NCC(Nc12)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N
Canonical SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1CNc2c(N1)c(=O)nc([nH]2)N
InChI:
InChI=1S/C19H23N7O6/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/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
InChIKey:
MSTNYGQPCMXVAQ-KIYNQFGBSA-N

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
IUPAC Traditional name
@tetrahydrofolic acid
tetrahydrofolic acid
Synonyms
tetrahydropteroylglutamate
tetrahydropteroyl mono-L-glutamate
tetrahydrafolate
tetra-H-folate
tetrahydrofolate
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)glutamic acid
H4PteGlu
th-folate
THF
folate-H4
FH4
5,6,7,8-tetrahydrofolic acid
5,6,7,8-tetrahydrofolate
(6S)-tetrahydrofolate
Tetrahydrofolic acid
N-[4-[[(2-Amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid
(-)-L-5,6,7,8-Tetrahydrofolic Acid
THFA
Tetrahydropteroylglutamic Acid
L-Tetrahydrofolic Acid, synthesized on receipt of order. 95% minimum purity when shipped.
CAS Number
135-16-0
29347-89-5
PubChem SID
160963466
46504756
PubChem CID
91443
CHEBI ID
20506
Chemspider ID
82572
DrugBank ID
DB00116
KEGG ID
C00101
MeSH Name
5,6,7,8-tetrahydrofolic+acid
Wikipedia Title
Tetrahydrofolic_acid

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
T293515 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.4210246  H Acceptors 12 
H Donor LogD (pH = 5.5) -5.826242 
LogD (pH = 7.4) -8.4603615  Log P -2.6668603 
Molar Refractivity 121.3866 cm3 Polarizability 41.3385 Å3
Polar Surface Area 207.27 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.96  LOG S -3.22 
Solubility (Water) 2.69e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Hydrophobicity(logP)
-2.7 expand Show data source
Storage Warning
We have observed that this material decomposes steadily over expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia DrugBank DrugBank TRC TRC
DrugBank - DB00116 external link
Item Information
Drug Groups approved; nutraceutical
Description Tetrahydrofolic acid is a folic acid derivative. It is produced from dihydrofolic acid by dihydrofolate reductase.
It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase. It is a coenzyme in many reactions, especially in the metabolism of amino acids and nucleic acids. It acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes.
Indication For nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Tetrahydrofolate is the main active metabolite of dietary folate. It is vital as a coenzyme in reactions involving transfers of single carbon groups. Tetrahydrofolate has a role in nucleic and amino acid synthesis. As nucleic and amino acid synthesis is affected by a deficiency of tetrahydrofolate, actively dividing and growing cells tend to be the first affected. Tetrahydrofolate is used to treat topical sprue and megaloblastic and macrocytic anemias, hematologic complications resulting from a deficiency in folic acid.
Affected Organisms
Humans and other mammals
External Links
Wikipedia
Toronto Research Chemicals - T293515 external link
A folic acid derivative and coenzyme involved in the metabolism of amino and nucleic acids. We have observed that this material decomposes steadily over time. Use immediately upon receipt.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Prinz-Langenohl, R., et al.: Brit. J. Pharmacol., 158, 2014 (2009)
  • • Martin, H., et al.: Anal. Biochem., 402, 137 (2009)
  • • Dasarathy, J., et al.: Am. J. Clin. Nut., 91, 357 (2009)
  • • Karas-Kuzelicki, N., et al.: Clin. Biochem., 43, 37 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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