5,6-Cyclic-Tetrahydropteridine

Identification

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Name
5,6-Cyclic-Tetrahydropteridine
Accession Number
DB03332  (EXPT00534)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 223.1888
Monoisotopic: 223.070539179
Chemical Formula
C8H9N5O3
InChI Key
XAZOBOCYEGBXHD-GSVOUGTGSA-N
InChI
InChI=1S/C8H9N5O3/c9-7-11-5-4(6(14)12-7)13-3(1-10-5)2-16-8(13)15/h3H,1-2H2,(H4,9,10,11,12,14)/t3-/m1/s1
IUPAC Name
(6aR)-3-amino-1H,2H,5H,6H,6aH,7H,9H-[1,3]oxazolo[3,4-f]pteridine-1,9-dione
SMILES
NC1=NC2=C(N3[C@@H](COC3=O)CN2)C(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHumans
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6323220
PubChem Substance
46505882
ChemSpider
4883327
HET
AP4
PDB Entries
1dmj

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 Solubility4.26 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.08ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.05 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.18 m3·mol-1ChemAxon
Polarizability20 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.927
Caco-2 permeable-0.6588
P-glycoprotein substrateNon-substrate0.5291
P-glycoprotein inhibitor INon-inhibitor0.9293
P-glycoprotein inhibitor IINon-inhibitor0.9875
Renal organic cation transporterNon-inhibitor0.8254
CYP450 2C9 substrateNon-substrate0.8273
CYP450 2D6 substrateNon-substrate0.8095
CYP450 3A4 substrateNon-substrate0.6224
CYP450 1A2 substrateNon-inhibitor0.6271
CYP450 2C9 inhibitorNon-inhibitor0.8591
CYP450 2D6 inhibitorNon-inhibitor0.8248
CYP450 2C19 inhibitorNon-inhibitor0.7856
CYP450 3A4 inhibitorNon-inhibitor0.7707
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9178
Ames testNon AMES toxic0.5677
CarcinogenicityNon-carcinogens0.9112
BiodegradationNot ready biodegradable0.9533
Rat acute toxicity2.4637 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9792
hERG inhibition (predictor II)Non-inhibitor0.7438
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 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
Secondary alkylarylamines / Pyrimidones / Aminopyrimidines and derivatives / Oxazolidinones / Vinylogous amides / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Oxacyclic compounds / Azacyclic compounds
show 5 more
Substituents
Pterin / Aminopyrimidine / Pyrimidone / Secondary aliphatic/aromatic amine / Oxazolidinone / Pyrimidine / Oxazolidine / Heteroaromatic compound / Vinylogous amide / Carbamic acid ester
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 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]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:49