NAV

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

Identification

Generic Name
(6S)-5,6,7,8-tetrahydrofolic acid
DrugBank Accession Number
DB02031
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 445.4292
Monoisotopic: 445.170981503
Chemical Formula
C19H23N7O6
Synonyms
  • (6S)-5,6,7,8-tetrahydrofolate
  • (6S)-5,6,7,8-tetrahydropteroylglutamate
  • (6S)-H4folate
  • (6S)-tetrahydrofolate
  • (6S)-Tetrahydrofolic acid
  • (6S)-THFA
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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
Integrate drug-drug
interactions in your software
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 (6S)-5,6,7,8-tetrahydrofolic acid can be decreased when it is combined with Carbamazepine.
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.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
5,6,7,8-tetrahydrofolic acid (CHEBI:15635)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
135-16-0
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

References

General References
Not Available
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 21 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSsplash10-0002-0090300000-c66445bc20ac1f82390b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0002900000-35b628373d45ea988124
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0491100000-f9ef32fa86548c9631c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f7p-1907500000-628c8741ff9fb2d296a7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0933000000-b0059c0e5794f5354d85
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-4916500000-4af506f14ea619ef144f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.95033
predicted
DeepCCS 1.0 (2019)
[M+H]+198.3459
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.25842
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Nitric oxide synthase oxygenase
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. [Article]
  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. [Article]
Details2. Thymidylate synthase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52