NP-MRD: Showing NP-Card for 2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine (NP0086772)

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Record Information

Version

2.0

Created at

2022-05-11 16:30:33 UTC

Updated at

2022-05-11 16:30:33 UTC

NP-MRD ID

NP0086772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine

Description

2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine 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. 2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine is a moderately basic compound (based on its pKa). This compound It is a byproduct of 6-pyruvoyltetrahydropterin synthase (EC4.2.3.12), And associated with 6-Pyruvoyltetrahydropterin synthase deficiency (an autosomal recessive disorder that causes malignant hyperphenylalaninemia due to tetrahydrobiopterin deficiency).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.0017    0.4509    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   -0.0200    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6109   -1.0092   -0.4011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649    0.6389    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089    1.6392    1.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1153    0.2340    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579    0.9144    0.8237 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    0.6781    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -0.3707   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104   -0.6434   -0.5904 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8183    0.0899   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   -0.1736   -0.3912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000    1.1106    0.7225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321    1.4237    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    2.3765    1.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722   -1.1573   -0.8245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288   -2.2308   -1.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960   -0.8710   -0.5733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4876   -0.6278   -1.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3412   -0.0174    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    1.5539    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7749    0.1709    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9279    0.5367   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4506   -1.1690   -0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.7003    1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -1.9362   -2.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -1.8029   -0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -1.4889   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  6  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 17 26  1  0
 18 27  1  1
 19 28  1  0
M  END


  Mrv0541 02231219072D          

 19 20  0  0  0  0            999 V2000
   -0.7150    0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    0.7392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -0.9144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267   -0.9110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    0.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452    0.3300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    1.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069   -1.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -0.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568   -0.9144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    1.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  2  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C(=O)C1=NC2=C(N=C(N)NC2=O)N(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9N5O5/c1-2(15)5(16)3-8(18)14(19)6-4(11-3)7(17)13-9(10)12-6/h8,18-19H,1H3,(H3,10,12,13,17)

> <INCHI_KEY>
QBHQZPRDJMYEDG-UHFFFAOYSA-N

> <FORMULA>
C9H9N5O5

> <MOLECULAR_WEIGHT>
267.1983

> <EXACT_MASS>
267.060368423

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
23.40354548297836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-amino-7,8-dihydroxy-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)propane-1,2-dione

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-1.1608298633333332

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.57651273516727

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.766025767358233

> <JCHEM_PKA_STRONGEST_BASIC>
2.2642758924402

> <JCHEM_POLAR_SURFACE_AREA>
157.68

> <JCHEM_REFRACTIVITY>
69.80969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-amino-7,8-dihydroxy-4-oxo-3,7-dihydropteridin-6-yl)propane-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.335   0.616   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.341  -0.931   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.006   1.380   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.663   1.380   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.006  -1.707   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -2.663  -1.701   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.341   0.603   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -4.004   0.616   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -2.663   2.926   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.335  -0.937   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.013  -3.254   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.004  -0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.670   1.373   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.670  -1.720   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -5.333  -1.707   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.004   0.616   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.663   2.920   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.333   1.380   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.004  -0.931   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   10                                                  
CONECT    8    4   12                                                       
CONECT    9    4                                                            
CONECT   10    5   14    7                                                  
CONECT   11    5                                                            
CONECT   12    6   15    8                                                  
CONECT   13    7   16   17                                                  
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   13   18   19                                                  
CONECT   17   13                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₉N₅O₅

Average Mass

267.1983 Da

Monoisotopic Mass

267.06037 Da

IUPAC Name

1-(2-amino-7,8-dihydroxy-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)propane-1,2-dione

Traditional Name

1-(2-amino-7,8-dihydroxy-4-oxo-3,7-dihydropteridin-6-yl)propane-1,2-dione

CAS Registry Number

Not Available

SMILES

CC(=O)C(=O)C1=NC2=C(N=C(N)NC2=O)N(O)C1O

InChI Identifier

InChI=1S/C9H9N5O5/c1-2(15)5(16)3-8(18)14(19)6-4(11-3)7(17)13-9(10)12-6/h8,18-19H,1H3,(H3,10,12,13,17)

InChI Key

QBHQZPRDJMYEDG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Alpha-diketone
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Ketimine
Ketone
Alkanolamine
Azacycle
N-organohydroxylamine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Imine
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.83	ALOGPS
logP	-1.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.77	ChemAxon
pKa (Strongest Basic)	2.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	157.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.81 m³·mol⁻¹	ChemAxon
Polarizability	23.4 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

HMDB0001410

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022605

KNApSAcK ID

Not Available

Chemspider ID

389496

KEGG Compound ID

C05255

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135532281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine (NP0086772)

MOL for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

3D MOL for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

3D SDF for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

3D-SDF for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

PDB for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

3D PDB for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

SMILES for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

INCHI for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

Structure for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)

3D Structure for NP0086772 (2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine)