D-threo-neopterin

Identification

Name
D-threo-neopterin
Accession Number
DB02385  (EXPT02326)
Type
Small Molecule
Groups
Experimental
Description

A pteridine derivative present in body fluids; elevated levels result from immune system activation, malignant disease, allograft rejection, and viral infections. (From Stedman, 26th ed) Neopterin also serves as a precursor in the biosynthesis of biopterin.

Structure
Thumb
Synonyms
  • D-monapterin
  • D-threo-monapterin
  • Monapterin
  • Neopterin D-threo-form
Categories
UNII
26C7CRZ5LJ
CAS number
10162-32-0
Weight
Average: 253.2147
Monoisotopic: 253.081103865
Chemical Formula
C9H11N5O4
InChI Key
BMQYVXCPAOLZOK-INEUFUBQSA-N
InChI
InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m1/s1
IUPAC Name
2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydropteridin-4-one
SMILES
NC1=NC2=NC=C(N=C2C(=O)N1)[C@@H](O)[C@H](O)CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
PathwayCategory
Segawa SyndromeDisease
Hyperphenylalaniemia Due to Guanosine Triphosphate Cyclohydrolase DeficiencyDisease
Pterine BiosynthesisMetabolic
DOPA-Responsive DystoniaDisease
Hyperphenylalaninemia Due to DHPR-DeficiencyDisease
Pterine BiosynthesisMetabolic
Hyperphenylalaninemia Due to 6-Pyruvoyltetrahydropterin Synthase Deficiency (ptps)Disease
Sepiapterin Reductase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C05926
PubChem Compound
444632
PubChem Substance
46506345
ChemSpider
392507
HET
NEO
Wikipedia
Neopterin
PDB Entries
1br5

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 Solubility6.26 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.99ChemAxon
pKa (Strongest Basic)0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.95 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.11 m3·mol-1ChemAxon
Polarizability23.35 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9673
Blood Brain Barrier+0.78
Caco-2 permeable-0.7695
P-glycoprotein substrateSubstrate0.5466
P-glycoprotein inhibitor INon-inhibitor0.9729
P-glycoprotein inhibitor IINon-inhibitor0.9949
Renal organic cation transporterNon-inhibitor0.9417
CYP450 2C9 substrateNon-substrate0.8613
CYP450 2D6 substrateNon-substrate0.8
CYP450 3A4 substrateNon-substrate0.6416
CYP450 1A2 substrateNon-inhibitor0.84
CYP450 2C9 inhibitorNon-inhibitor0.9052
CYP450 2D6 inhibitorNon-inhibitor0.9236
CYP450 2C19 inhibitorNon-inhibitor0.9046
CYP450 3A4 inhibitorNon-inhibitor0.9209
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9763
Ames testNon AMES toxic0.736
CarcinogenicityNon-carcinogens0.9233
BiodegradationNot ready biodegradable0.9706
Rat acute toxicity2.1247 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9893
hERG inhibition (predictor II)Non-inhibitor0.9128
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Pterins and derivatives
Direct Parent
Biopterins and derivatives
Alternative Parents
Pyrimidones / Aminopyrimidines and derivatives / Pyrazines / Vinylogous amides / Heteroaromatic compounds / Secondary alcohols / Polyols / Azacyclic compounds / Primary amines / Primary alcohols
show 4 more
Substituents
Biopterin / Aminopyrimidine / Pyrimidone / Pyrazine / Pyrimidine / Heteroaromatic compound / Vinylogous amide / Secondary alcohol / Polyol / Azacycle
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
neopterins (CHEBI:28670)

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:16