5-hydroxymethyl-5,6-dihydrofolic acid

Identification

Name
5-hydroxymethyl-5,6-dihydrofolic acid
Accession Number
DB02800
Description
Not Available
Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 473.4393
Monoisotopic: 473.165896125
Chemical Formula
C20H23N7O7
Synonyms
Not Available

Pharmacology

Pharmacology
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Indication
Not Available
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine hydroxymethyltransferase, cytosolicNot AvailableHumans
UProbable 5-formyltetrahydrofolate cyclo-ligaseNot AvailableMycoplasma pneumoniae (strain ATCC 29342 / M129)
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
Medicalerrors
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Glutamic acid and derivatives
Alternative Parents
Hippuric acids / N-acyl-alpha amino acids / Pterins and derivatives / Aminobenzamides / Phenylalkylamines / Benzoyl derivatives / Aniline and substituted anilines / Dialkylarylamines / Secondary alkylarylamines / Aminopyrimidines and derivatives
show 16 more
Substituents
Alkanolamine / Amine / Amino acid / Aminobenzamide / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzamide
show 36 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hemiaminal, 5,6-dihydrofolic acid (CHEBI:45981)

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IIEPLRAFVCMHQF-STQMWFEESA-N
InChI
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,8,12-13,22,28H,5-7,9H2,(H,24,31)(H,29,30)(H,33,34)(H3,21,25,26,32)/t12-,13-/m0/s1
IUPAC Name
(2S)-2-{[4-({[(6S)-2-amino-5-(hydroxymethyl)-4-oxo-3,4,5,6-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
NC1=NC2=C(N(CO)[C@@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=N2)C(=O)N1

References

General References
Not Available
PubChem Compound
6323516
PubChem Substance
46505894
ChemSpider
4883457
ChEBI
45981
ZINC
ZINC000012502643
PDBe Ligand
THF
PDB Entries
1eji / 1u3g / 2tdd / 3sux / 4o7u

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 Solubility0.192 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)3.52ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area219.04 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.45 m3·mol-1ChemAxon
Polarizability46.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6712
Blood Brain Barrier-0.5654
Caco-2 permeable-0.8646
P-glycoprotein substrateSubstrate0.7752
P-glycoprotein inhibitor INon-inhibitor0.9079
P-glycoprotein inhibitor IINon-inhibitor0.9734
Renal organic cation transporterNon-inhibitor0.7662
CYP450 2C9 substrateNon-substrate0.8187
CYP450 2D6 substrateNon-substrate0.8075
CYP450 3A4 substrateNon-substrate0.5692
CYP450 1A2 substrateNon-inhibitor0.6792
CYP450 2C9 inhibitorNon-inhibitor0.8904
CYP450 2D6 inhibitorNon-inhibitor0.8927
CYP450 2C19 inhibitorNon-inhibitor0.8919
CYP450 3A4 inhibitorNon-inhibitor0.845
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9734
Ames testNon AMES toxic0.6561
CarcinogenicityNon-carcinogens0.8911
BiodegradationNot ready biodegradable0.9511
Rat acute toxicity2.4024 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9331
hERG inhibition (predictor II)Non-inhibitor0.5391
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine binding
Specific Function
Interconversion of serine and glycine.
Gene Name
SHMT1
Uniprot ID
P34896
Uniprot Name
Serine hydroxymethyltransferase, cytosolic
Molecular Weight
53082.18 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Mycoplasma pneumoniae (strain ATCC 29342 / M129)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in folate metabolism. Catalyzes the irreversible conversion of 5-formyltetrahydrofolate (5-FTHF) to yield 5,10-methenyltetrahydrofolate.
Gene Name
Not Available
Uniprot ID
P75430
Uniprot Name
5-formyltetrahydrofolate cyclo-ligase
Molecular Weight
19265.185 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 13:24 / Updated on June 12, 2020 16:52