Identification

Generic Name
Pteroic acid
DrugBank Accession Number
DB04196
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 312.2835
Monoisotopic: 312.09708828
Chemical Formula
C14H12N6O3
Synonyms
Not Available
External IDs
  • NSC-14972

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydropteroate synthaseNot AvailableBacillus anthracis
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
Adverseeffects
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Pterins and derivatives
Direct Parent
Pterins and derivatives
Alternative Parents
Aminobenzoic acids / Benzoic acids / Phenylalkylamines / Aniline and substituted anilines / Benzoyl derivatives / Secondary alkylarylamines / Pyrimidones / Aminopyrimidines and derivatives / Pyrazines / Vinylogous amides
show 10 more
Substituents
Amine / Amino acid / Amino acid or derivatives / Aminobenzoic acid / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pteroic acid (CHEBI:27623)
Affected organisms
Not Available

Chemical Identifiers

UNII
8258W48TBZ
CAS number
119-24-4
InChI Key
JOAQINSXLLMRCV-UHFFFAOYSA-N
InChI
InChI=1S/C14H12N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,6,16H,5H2,(H,22,23)(H3,15,17,19,20,21)
IUPAC Name
4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoic acid
SMILES
NC1=NC2=NC=C(CNC3=CC=C(C=C3)C(O)=O)N=C2C(=O)N1

References

Synthesis Reference

Le-Cun Xu, Iontcho Radoslavov Vlahov, Christopher Paul Leamon, Hari Krishna Santhapuram, Chunhong Li, "Synthesis and Purification of Pteroic Acid and Conjugates Thereof." U.S. Patent US20080207625, issued August 28, 2008.

US20080207625
General References
Not Available
KEGG Compound
C07582
PubChem Compound
95054
PubChem Substance
46505016
ChemSpider
85769
BindingDB
6645
ChEBI
37066
ChEMBL
CHEMBL341824
ZINC
ZINC000006628789
PDBe Ligand
PT1
PDB Entries
1br6 / 1hwp / 1tx0 / 3tr9 / 3tyu / 5u10 / 6jwr / 6jws / 6jwt / 6ofw
show 1 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 Solubility0.0942 mg/mLALOGPS
logP0.36ALOGPS
logP-0.022ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.59 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.36 m3·mol-1ChemAxon
Polarizability30.63 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9911
Blood Brain Barrier+0.8185
Caco-2 permeable-0.7104
P-glycoprotein substrateNon-substrate0.5246
P-glycoprotein inhibitor INon-inhibitor0.9721
P-glycoprotein inhibitor IINon-inhibitor0.9768
Renal organic cation transporterNon-inhibitor0.858
CYP450 2C9 substrateNon-substrate0.8416
CYP450 2D6 substrateNon-substrate0.7931
CYP450 3A4 substrateNon-substrate0.658
CYP450 1A2 substrateNon-inhibitor0.8115
CYP450 2C9 inhibitorNon-inhibitor0.8999
CYP450 2D6 inhibitorNon-inhibitor0.8958
CYP450 2C19 inhibitorNon-inhibitor0.8901
CYP450 3A4 inhibitorNon-inhibitor0.8524
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.921
Ames testNon AMES toxic0.7988
CarcinogenicityNon-carcinogens0.9118
BiodegradationNot ready biodegradable0.9725
Rat acute toxicity2.2368 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9685
hERG inhibition (predictor II)Non-inhibitor0.8868
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

Drugtargets2
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Kind
Protein
Organism
Bacillus anthracis
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
Gene Name
folP
Uniprot ID
Q81VW8
Uniprot Name
Dihydropteroate synthase
Molecular Weight
30975.455 Da
References
  1. 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. [Article]

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