ChemFOnt: Showing chemical card for Isoxanthopterin (CFc000000555)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:58 UTC

Chemfont ID

CFc000000555

Molecule Identification

Common Name

Isoxanthopterin

Definition

Isoxanthopterin is a pteridine normally present in plasma, urine, and other bodily fluids also vary from normal concentrations in some disease states and also have diagnostic value. Pteridines' urinary concentrations seem to vary independently from each other and from normal values to yield a pattern of excreted pteridines that is diagnostic for different species, tissues, and tumor types. Intravenous or intramuscular administration of isoxanthopterin inhibits the growth rates of animal tumor models. Pteridin derivatives are a family of organic compound with very similar chemical structures which play an important biochemistry role. Pteridines metabolism and its regulation in normal and pathological conditions have not been extensively investigated due to the difficulty of their quantification. A significant decrease of isoxanthopterin has been determined in cancer patients. (PMID 15837549 , 9800651 ). Xanthine dehydrogenase (XDH) is the enzymes responsible for the conversion of xanthine to uric acid. It requires the presence of the molybdenum cofactor for its proper functioning. XDH is reported to have additional functions, i.e., the conversion of pterin to isoxanthopterin, one of the steps the degradation pathway of 5,6,7,8-tetrahydrobiopterin (BH4). Isoxanthopterin is very low in some cases of hereditary xanthinuria (OMIM 278300 ) and molybdenum cofactor deficiency (OMIM 252150 ). (PMID: 8812740 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-4,7-dihydroxypteridine	ChEBI
2-Amino-3H,8H-pteridine-4,7-dione	HMDB
2-Aminopteridine-4,7-diol	HMDB
Isoxanthopterin	ChEBI

Chemical Formula

C₆H₅N₅O₂

Average Molecular Weight

179.1362

Monoisotopic Molecular Weight

179.044324429

IUPAC Name

2-amino-1,4,7,8-tetrahydropteridine-4,7-dione

Traditional Name

2-amino-1,8-dihydropteridine-4,7-dione

CAS Registry Number

529-69-1

SMILES

NC1=NC(=O)C2=C(N1)NC(=O)C=N2

InChI Identifier

InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)

InChI Key

GLKCOBIIZKYKFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Pterin
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Vinylogous amide
Heteroaromatic compound
Lactam
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxypteridine (CHEBI:16713 )
a small molecule (2-AMINO-47-DIHYDROXYPTERIDINE )

Functional Ontology

Not Available

Urine (PMID: 22624806)

Cellular substructure

Cytoplasm (HMDB: HMDB0000704)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000704)

Source

Endogenous

Endogenous (HMDB: HMDB0000704)

Plant

Glycine Max (HMDB: HMDB0000704)

Exogenous

Food

Food (HMDB: HMDB0000704)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Soy

Soy bean (FooDB: FOOD00085)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.46 g/L	ALOGPS
logP	-0.96	ALOGPS
logP	-1.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.37	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.94 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51.84 m³·mol⁻¹	ChemAxon
Polarizability	15.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000704

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5672

PubChem Compound

10729

PDB ID

Not Available

ChEBI ID

16713

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Taylor, Edward C.; Abdulla, Riaz F.; Tanaka, Kunihiko; Jacobi, Peter A. Pteridines. XXXVI. Syntheses of xanthopterin and isoxanthopterin. Application of N-oxide chemistry to highly functionalized pyrazines and pteridines. Journal of Organic Chemistry (1975), 40(16), 2341-7.

Showing chemical card for Isoxanthopterin (CFc000000555)

MOL for CFc000000555 (Isoxanthopterin)

3D MOL for CFc000000555 (Isoxanthopterin)

3D SDF for CFc000000555 (Isoxanthopterin)

3D-SDF for CFc000000555 (Isoxanthopterin)

PDB for CFc000000555 (Isoxanthopterin)

3D PDB for CFc000000555 (Isoxanthopterin)

SMILES for CFc000000555 (Isoxanthopterin)

INCHI for CFc000000555 (Isoxanthopterin)

Structure for CFc000000555 (Isoxanthopterin)

3D Structure for CFc000000555 (Isoxanthopterin)