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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:05 UTC

HMDB ID

HMDB0000704

Secondary Accession Numbers

HMDB00704

Metabolite Identification

Common Name

Isoxanthopterin

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Isoxanthopterin.mol
  Mrv1652305271900172D          

 13 14  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  2  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000704

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C6H5N5O2

> <MOLECULAR_WEIGHT>
179.1362

> <EXACT_MASS>
179.044324429

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.29575268682585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-1,4,7,8-tetrahydropteridine-4,7-dione

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-1.7413570219999999

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.734783756526987

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.36612496484554

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0168120220579113

> <JCHEM_POLAR_SURFACE_AREA>
108.94

> <JCHEM_REFRACTIVITY>
51.84449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-1,8-dihydropteridine-4,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isoxanthopterin.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334   0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8    6                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000704)

Excreta

Biofluid or Excreta

Urine (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

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Soy

Soy bean (FooDB: FOOD00085)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.005 mg/mL	Not Available
LogP	-3.760 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.705	31661259
DarkChem	[M-H]-	138.573	31661259
AllCCS	[M+H]+	137.798	32859911
AllCCS	[M-H]-	133.353	32859911
DeepCCS	[M+H]+	137.925	30932474
DeepCCS	[M-H]-	135.529	30932474
DeepCCS	[M-2H]-	170.638	30932474
DeepCCS	[M+Na]+	145.927	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	134.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoxanthopterin	NC1=NC(=O)C2=C(N1)NC(=O)C=N2	2902.3	Standard polar	33892256
Isoxanthopterin	NC1=NC(=O)C2=C(N1)NC(=O)C=N2	2008.8	Standard non polar	33892256
Isoxanthopterin	NC1=NC(=O)C2=C(N1)NC(=O)C=N2	2385.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoxanthopterin,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	2223.7	Semi standard non polar	33892256
Isoxanthopterin,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	2358.4	Standard non polar	33892256
Isoxanthopterin,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	3665.0	Standard polar	33892256
Isoxanthopterin,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	2161.6	Semi standard non polar	33892256
Isoxanthopterin,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	2261.1	Standard non polar	33892256
Isoxanthopterin,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	3551.7	Standard polar	33892256
Isoxanthopterin,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	2176.2	Semi standard non polar	33892256
Isoxanthopterin,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	2290.9	Standard non polar	33892256
Isoxanthopterin,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	3494.1	Standard polar	33892256
Isoxanthopterin,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C	2024.1	Semi standard non polar	33892256
Isoxanthopterin,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C	2340.0	Standard non polar	33892256
Isoxanthopterin,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C	3382.5	Standard polar	33892256
Isoxanthopterin,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2	2075.5	Semi standard non polar	33892256
Isoxanthopterin,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2	2420.3	Standard non polar	33892256
Isoxanthopterin,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2	3296.0	Standard polar	33892256
Isoxanthopterin,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C	2058.3	Semi standard non polar	33892256
Isoxanthopterin,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C	2390.1	Standard non polar	33892256
Isoxanthopterin,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C	3310.0	Standard polar	33892256
Isoxanthopterin,2TMS,isomer #4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C)C(=O)C=N2	2124.7	Semi standard non polar	33892256
Isoxanthopterin,2TMS,isomer #4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C)C(=O)C=N2	2366.8	Standard non polar	33892256
Isoxanthopterin,2TMS,isomer #4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C)C(=O)C=N2	3268.6	Standard polar	33892256
Isoxanthopterin,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2086.3	Semi standard non polar	33892256
Isoxanthopterin,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2376.7	Standard non polar	33892256
Isoxanthopterin,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2900.2	Standard polar	33892256
Isoxanthopterin,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2069.4	Semi standard non polar	33892256
Isoxanthopterin,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2405.5	Standard non polar	33892256
Isoxanthopterin,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2972.1	Standard polar	33892256
Isoxanthopterin,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2	2092.4	Semi standard non polar	33892256
Isoxanthopterin,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2	2437.8	Standard non polar	33892256
Isoxanthopterin,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2	2958.0	Standard polar	33892256
Isoxanthopterin,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2207.5	Semi standard non polar	33892256
Isoxanthopterin,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2472.1	Standard non polar	33892256
Isoxanthopterin,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)C=N2)[Si](C)(C)C	2626.2	Standard polar	33892256
Isoxanthopterin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	2382.6	Semi standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	2513.2	Standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2	3661.3	Standard polar	33892256
Isoxanthopterin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	2319.6	Semi standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	2483.4	Standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C(=O)C=N2	3524.0	Standard polar	33892256
Isoxanthopterin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	2366.0	Semi standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	2521.3	Standard non polar	33892256
Isoxanthopterin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C1[NH]C(N)=NC2=O	3485.5	Standard polar	33892256
Isoxanthopterin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C(C)(C)C	2445.2	Semi standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C(C)(C)C	2730.8	Standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)[NH]C(=O)C=N2)[Si](C)(C)C(C)(C)C	3326.9	Standard polar	33892256
Isoxanthopterin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2497.3	Semi standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2766.9	Standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	3260.6	Standard polar	33892256
Isoxanthopterin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C	2455.9	Semi standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C	2772.9	Standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C	3250.0	Standard polar	33892256
Isoxanthopterin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2515.0	Semi standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2762.2	Standard non polar	33892256
Isoxanthopterin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=N2	3231.5	Standard polar	33892256
Isoxanthopterin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	2639.0	Semi standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	2963.3	Standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	3006.4	Standard polar	33892256
Isoxanthopterin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2626.6	Semi standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2989.2	Standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]C(=O)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3038.0	Standard polar	33892256
Isoxanthopterin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2719.6	Semi standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	2999.5	Standard non polar	33892256
Isoxanthopterin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2	3050.3	Standard polar	33892256
Isoxanthopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	2898.8	Semi standard non polar	33892256
Isoxanthopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	3226.2	Standard non polar	33892256
Isoxanthopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C=N2)[Si](C)(C)C(C)(C)C	2931.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isoxanthopterin GC-EI-TOF (Non-derivatized)	splash10-000t-2926000000-3e81d07c48126369454e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoxanthopterin GC-EI-TOF (Non-derivatized)	splash10-000t-2926000000-3e81d07c48126369454e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxanthopterin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004r-3900000000-6d52e641b19d9e4047cc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxanthopterin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxanthopterin 35V, Positive-QTOF	splash10-03ei-0900000000-f5ddc076cf5087744fc4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxanthopterin 35V, Negative-QTOF	splash10-000i-0900000000-9eabc8aa87793cdfe0a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 10V, Positive-QTOF	splash10-001i-0900000000-346d30fbd19239c12668	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 20V, Positive-QTOF	splash10-001i-0900000000-ae540741799c106adfaa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 40V, Positive-QTOF	splash10-02t9-6900000000-ea5575a0190e3edb08e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 10V, Negative-QTOF	splash10-004i-0900000000-d365a350a3179cec642b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 20V, Negative-QTOF	splash10-004i-0900000000-187538c79b1568c2cd86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 40V, Negative-QTOF	splash10-0006-9200000000-7636a27e3e5a1a090913	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 10V, Positive-QTOF	splash10-001i-0900000000-4f23160ef2f9d2ffc80d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 20V, Positive-QTOF	splash10-001i-0900000000-4f23160ef2f9d2ffc80d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 40V, Positive-QTOF	splash10-03di-8900000000-87dc857ea0e8355ef9f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 10V, Negative-QTOF	splash10-004i-0900000000-33a3626771c44086c430	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 20V, Negative-QTOF	splash10-004i-0900000000-8f69a9fa967d517f5c27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxanthopterin 40V, Negative-QTOF	splash10-014u-9400000000-4cbf501aa1438ddc0d13	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22624806	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Not Available	22624806	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1252971

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Boltshauser E, Niederwieser A, Kierat L, Haenggeli CA: Pterins in patients with Rett syndrome. Am J Med Genet Suppl. 1986;1:317-21. [PubMed:3087192 ]
Krumdieck CL, Fukushima K, Fukushima T, Shiota T, Butterworth CE Jr: A long-term study of the excretion of folate and pterins in a human subject after ingestion of 14C folic acid, with observations on the effect of diphenylhydantoin administration. Am J Clin Nutr. 1978 Jan;31(1):88-93. [PubMed:413430 ]
Han F, Huynh BH, Shi H, Lin B, Ma Y: Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1999 Apr 1;71(7):1265-9. [PubMed:10204031 ]
Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Yamakita J, Nasako Y, Hiroishi K, Higashino K: Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):395-400. [PubMed:8811453 ]
Lord JL, de Peyster A, Quintana PJ, Metzger RP: Cytotoxicity of xanthopterin and isoxanthopterin in MCF-7 cells. Cancer Lett. 2005 May 10;222(1):119-24. [PubMed:15837549 ]
Espinosa-Mansilla A, Duran-Meras I, Salinas F: Simultaneous determination of pteridines in multicomponent mixtures using derivative spectrophotometry and partial least-squares calibration. J Pharm Biomed Anal. 1998 Sep;17(8):1325-34. [PubMed:9800651 ]
Blau N, de Klerk JB, Thony B, Heizmann CW, Kierat L, Smeitink JA, Duran M: Tetrahydrobiopterin loading test in xanthine dehydrogenase and molybdenum cofactor deficiencies. Biochem Mol Med. 1996 Aug;58(2):199-203. [PubMed:8812740 ]

Showing metabocard for Isoxanthopterin (HMDB0000704)

MOL for HMDB0000704 (Isoxanthopterin)

3D MOL for HMDB0000704 (Isoxanthopterin)

3D SDF for HMDB0000704 (Isoxanthopterin)

3D-SDF for HMDB0000704 (Isoxanthopterin)

PDB for HMDB0000704 (Isoxanthopterin)

3D PDB for HMDB0000704 (Isoxanthopterin)

SMILES for HMDB0000704 (Isoxanthopterin)

INCHI for HMDB0000704 (Isoxanthopterin)

Structure for HMDB0000704 (Isoxanthopterin)

3D Structure for HMDB0000704 (Isoxanthopterin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra