(6S)-5,6,7,8-tetrahydrofolic acid

Identification

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Name
(6S)-5,6,7,8-tetrahydrofolic acid
Accession Number
DB02031  (EXPT03050)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (6S)-5,6,7,8-tetrahydrofolate
  • (6S)-5,6,7,8-tetrahydropteroylglutamate
  • (6S)-H4folate
  • (6S)-tetrahydrofolate
  • (6S)-Tetrahydrofolic acid
  • (6S)-THFA
Categories
UNII
Not Available
CAS number
135-16-0
Weight
Average: 445.4292
Monoisotopic: 445.170981503
Chemical Formula
C19H23N7O6
InChI Key
MSTNYGQPCMXVAQ-RYUDHWBXSA-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
IUPAC Name
(2S)-2-{[4-({[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
NC1=NC2=C(N[C@@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase oxygenaseNot AvailableBacillus subtilis (strain 168)
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
5-fluorouridineThe risk or severity of adverse effects can be increased when (6S)-5,6,7,8-tetrahydrofolic acid is combined with 5-fluorouridine.
AminopterinThe therapeutic efficacy of Aminopterin can be decreased when used in combination with (6S)-5,6,7,8-tetrahydrofolic acid.
BrodimoprimThe therapeutic efficacy of Brodimoprim can be decreased when used in combination with (6S)-5,6,7,8-tetrahydrofolic acid.
CapecitabineThe risk or severity of adverse effects can be increased when (6S)-5,6,7,8-tetrahydrofolic acid is combined with Capecitabine.
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with (6S)-5,6,7,8-tetrahydrofolic acid.
ColestipolThe serum concentration of (6S)-5,6,7,8-tetrahydrofolic acid can be decreased when it is combined with Colestipol.
CycloguanilThe therapeutic efficacy of Cycloguanil can be decreased when used in combination with (6S)-5,6,7,8-tetrahydrofolic acid.
DapsoneThe therapeutic efficacy of Dapsone can be decreased when used in combination with (6S)-5,6,7,8-tetrahydrofolic acid.
DoxifluridineThe risk or severity of adverse effects can be increased when (6S)-5,6,7,8-tetrahydrofolic acid is combined with Doxifluridine.
FlucytosineThe risk or severity of adverse effects can be increased when (6S)-5,6,7,8-tetrahydrofolic acid is combined with Flucytosine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5460413
PubChem Substance
46508587
ChemSpider
4573946
ChEBI
15635
ZINC
ZINC000004228237
PDBe Ligand
THG
PDB Entries
1kzi / 1m7v / 1m7z / 1u22 / 1woo / 2yck / 3bhl / 3bhr / 3g5r / 3gsi
show 18 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.288 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area207.27 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.59 m3·mol-1ChemAxon
Polarizability44.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5181
Blood Brain Barrier-0.533
Caco-2 permeable-0.8443
P-glycoprotein substrateSubstrate0.7509
P-glycoprotein inhibitor INon-inhibitor0.972
P-glycoprotein inhibitor IINon-inhibitor0.9966
Renal organic cation transporterNon-inhibitor0.8752
CYP450 2C9 substrateNon-substrate0.8058
CYP450 2D6 substrateNon-substrate0.7984
CYP450 3A4 substrateNon-substrate0.637
CYP450 1A2 substrateNon-inhibitor0.9344
CYP450 2C9 inhibitorNon-inhibitor0.9265
CYP450 2D6 inhibitorNon-inhibitor0.9437
CYP450 2C19 inhibitorNon-inhibitor0.9215
CYP450 3A4 inhibitorNon-inhibitor0.9161
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9631
Ames testNon AMES toxic0.8293
CarcinogenicityNon-carcinogens0.954
BiodegradationNot ready biodegradable0.8759
Rat acute toxicity2.4563 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9534
hERG inhibition (predictor II)Non-inhibitor0.6623
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-005a-0321900000-806d326ed7665c62ee13
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0951300000-03607a01f0842f177170
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0920000000-a669623379da5ac89208
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0001900000-535971052b80b0699a2e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fbc-1346900000-37b6b740cafe7f89f238
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9441000000-d269bea3204e174044ce

Taxonomy

Description
This compound belongs to the class of organic compounds 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
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Pterins 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 / Pyrimidones / Secondary alkylarylamines / Aminopyrimidines and derivatives
show 12 more
Substituents
Tetrahydrofolic acid / Glutamic acid or derivatives / Hippuric acid or derivatives / Hippuric acid / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Benzamide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
5,6,7,8-tetrahydrofolic acid (CHEBI:15635)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Nitric-oxide synthase activity
Specific Function
Catalyzes the production of nitric oxide.
Gene Name
nos
Uniprot ID
O34453
Uniprot Name
Nitric oxide synthase oxygenase
Molecular Weight
41902.9 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on February 06, 2020 11:23