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Details

Stereochemistry EPIMERIC
Molecular Formula C19H23N7O6
Molecular Weight 445.4292
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRAHYDROFOLIC ACID

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

InChI

InChIKey=MSTNYGQPCMXVAQ-KIYNQFGBSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H23N7O6
Molecular Weight 445.4292
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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. 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. Tetrahydrofolic acid is used for nutritional supplementation, also for treating dietary shortage or imbalance.

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Tetrahydrofolic acid is used as a component of methotrexate chemotherapy treatment of Gestational Trophoblastic Neoplasms: methotrexate 100mg/m2, 200mg/m2, ivgtt, tetrahydrofolic acid (FA) 15mg q12h*4(24h after methotrexate injection),started at the first day of cycle, two weeks a cycle.
Route of Administration: Intravenous
In Vitro Use Guide
Tetrahydrofolic acid at 100 uM concentration didn`t significantly inhibit the specific binding of [3H]-KA to striatal membranes.
Substance Class Chemical
Record UNII
43ZWB253H4
Record Status Validated (UNII)
Record Version