NP-MRD: Showing NP-Card for 1,9-Dimethyluric acid (NP0001175)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:32 UTC

Updated at

2020-11-24 22:21:23 UTC

NP-MRD ID

NP0001175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,9-Dimethyluric acid

Description

1,9-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,9-Methyluracil is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316 , 15833286 , 3506820 , 15013152 ).

Structure

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


  Mrv1652305261923522D          

 14 15  0  0  0  0            999 V2000
   17.0475   -2.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8490   -4.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6185   -5.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5426   -5.2469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5426   -3.9191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3329   -4.1705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0475   -5.4081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7620   -4.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7620   -4.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0475   -3.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0240   -4.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3329   -4.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7989   -6.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6185   -3.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=C1NC(=O)N(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4O3/c1-10-4-3(8-6(10)13)5(12)11(2)7(14)9-4/h1-2H3,(H,8,13)(H,9,14)

> <INCHI_KEY>
UARKDOLETOEBCU-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O3

> <MOLECULAR_WEIGHT>
196.1634

> <EXACT_MASS>
196.059640142

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.82346459985554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,9-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-1.0968408043333333

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.791676820913171

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.690373334473463

> <JCHEM_PKA_STRONGEST_BASIC>
-5.879620269363435

> <JCHEM_POLAR_SURFACE_AREA>
81.75

> <JCHEM_REFRACTIVITY>
55.422

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,9-dimethyl-3,7-dihydropurine-2,6,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      31.822  -5.475   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.051  -8.555   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.155 -10.095   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      34.613  -9.794   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      34.613  -7.316   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      30.488  -7.785   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      31.822 -10.095   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      33.156  -9.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.156  -7.785   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.822  -7.015   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.511  -8.555   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.488  -9.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.091 -11.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.155  -7.015   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    8   11   13                                                  
CONECT    5    9   11                                                       
CONECT    6   10   12   14                                                  
CONECT    7    8   12                                                       
CONECT    8    4    7    9                                                  
CONECT    9    5    8   10                                                  
CONECT   10    1    6    9                                                  
CONECT   11    2    4    5                                                  
CONECT   12    3    6    7                                                  
CONECT   13    4                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
1,9-Dimethylate	Generator
1,9-Dimethylic acid	Generator
1,9-Dimethyl-2,6,8-trihydroxypurine	HMDB
7,9-Dihydro-1,9-dimethyl-1H-purine-2,6,8(3H)-trione	HMDB

Chemical Formula

C₇H₈N₄O₃

Average Mass

196.1634 Da

Monoisotopic Mass

196.05964 Da

IUPAC Name

1,9-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

Traditional Name

1,9-dimethyl-3,7-dihydropurine-2,6,8-trione

CAS Registry Number

55441-62-8

SMILES

CN1C(=O)NC2=C1NC(=O)N(C)C2=O

InChI Identifier

InChI=1S/C7H8N4O3/c1-10-4-3(8-6(10)13)5(12)11(2)7(14)9-4/h1-2H3,(H,8,13)(H,9,14)

InChI Key

UARKDOLETOEBCU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-08-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-12	View Spectrum

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 xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

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
Water Solubility	8.4 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.75 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	55.42 m³·mol⁻¹	ChemAxon
Polarizability	17.82 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

HMDB0002026

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022804

KNApSAcK ID

Not Available

Chemspider ID

97753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108712

PDB ID

Not Available

ChEBI ID

173963

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1,9-Dimethyluric acid (NP0001175)

MOL for NP0001175 (1,9-Dimethyluric acid)

3D MOL for NP0001175 (1,9-Dimethyluric acid)

3D SDF for NP0001175 (1,9-Dimethyluric acid)

3D-SDF for NP0001175 (1,9-Dimethyluric acid)

PDB for NP0001175 (1,9-Dimethyluric acid)

3D PDB for NP0001175 (1,9-Dimethyluric acid)

SMILES for NP0001175 (1,9-Dimethyluric acid)

INCHI for NP0001175 (1,9-Dimethyluric acid)

Structure for NP0001175 (1,9-Dimethyluric acid)

3D Structure for NP0001175 (1,9-Dimethyluric acid)