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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
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The toxicity of tetrahydrohomofolic acid in normal and malaria-infected monkeys.
1968 Feb
Thymidylate synthetase activity in the Novikoff hepatoma.
1976 Dec
Molecular cloning of the human placental folate transporter.
1995 Jan 17
Biosynthesis of tetrahydrofolate. Stereochemistry of dihydroneopterin aldolase.
2002 Aug 9
Folic acid and its metabolites modulate IGF-I receptor gene expression in colon cancer cells in a p53-dependent manner.
2006 Jun
Methotrexate induced differentiation in colon cancer cells is primarily due to purine deprivation.
2006 Sep 1
Enzymatic properties of ALDH1L2, a mitochondrial 10-formyltetrahydrofolate dehydrogenase.
2011 May 30
Tetrahydrofolate recognition by the mitochondrial folate transporter.
2011 Sep 9
Patents

Sample Use Guides

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.
Name Type Language
TETRAHYDROFOLIC ACID
DSC  
Common Name English
TETRAHYDROFOLIC ACID [DSC]
Common Name English
GLUTAMIC ACID, N-(P-(((2-AMINO-3,4,5,6,7,8-HEXAHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-, L-
Systematic Name English
5,6,7,8-TETRAHYDROFOLIC ACID
Common Name English
L-GLUTAMIC ACID, N-(4-(((2-AMINO-1,4,5,6,7,8-HEXAHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-
Systematic Name English
(-)-L-5,6,7,8-TETRAHYDROFOLIC ACID
Common Name English
Code System Code Type Description
CAS
135-16-0
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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SMS_ID
100000141677
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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DRUG BANK
DB00116
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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ECHA (EC/EINECS)
205-181-1
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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EVMPD
SUB96099
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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PUBCHEM
135444742
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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CHEBI
15635
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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CHEBI
20506
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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WIKIPEDIA
Tetrahydrofolic acid
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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EPA CompTox
DTXSID70897520
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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FDA UNII
43ZWB253H4
Created by admin on Sat Dec 16 08:12:16 GMT 2023 , Edited by admin on Sat Dec 16 08:12:16 GMT 2023
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