NP-MRD: Showing NP-Card for 1,3,9-Trimethyluric acid (NP0048504)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:30 UTC

Updated at

2022-03-17 20:57:30 UTC

NP-MRD ID

NP0048504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3,9-Trimethyluric acid

Description

1,3,9-Trimethyluric acid, also known as 1,3,9-trimethylate or 8-oxocaffeine, 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. 1,3,9-Trimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,9-Trimethyluric acid has been detected, but not quantified in, coffee and coffee products. This could make 1,3,9-trimethyluric acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217022D          

 15 16  0  0  0  0            999 V2000
   -1.7555   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -0.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671    0.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    0.7345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7555    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -0.7345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939    2.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492    1.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671    1.1427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -1.0613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -1.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -2.1230    0.0000 O   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
  2 13  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=C1N(C)C(=O)N(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N4O3/c1-10-5-4(9-7(10)14)6(13)12(3)8(15)11(5)2/h1-3H3,(H,9,14)

> <INCHI_KEY>
CWENCZHQIWXCCA-UHFFFAOYSA-N

> <FORMULA>
C8H10N4O3

> <MOLECULAR_WEIGHT>
210.19

> <EXACT_MASS>
210.075290206

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.75786885981796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.8731647386666664

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.778577822576182

> <JCHEM_PKA_STRONGEST_BASIC>
-5.633732262274788

> <JCHEM_POLAR_SURFACE_AREA>
72.96000000000001

> <JCHEM_REFRACTIVITY>
60.31869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,9-trimethyl-7H-purine-2,6,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.277  -0.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.752  -0.456   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.685   0.609   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.839  -0.001   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.752   1.371   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.277   1.371   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.143  -1.371   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.667  -1.371   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.295   3.963   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.839   2.591   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.685   2.133   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.820  -2.743   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.447  -1.981   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.075  -2.438   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.228  -3.963   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5                                                            
CONECT    7    4    8   14                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    5    9   11                                                  
CONECT   11    3   10                                                       
CONECT   12   13                                                            
CONECT   13    2   12   14                                                  
CONECT   14    7   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
1,3,9-Trimethylate	Generator
1,3,9-Trimethylic acid	Generator
1,3,9-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione	HMDB
7,9-Dihydro-1,3,9-trimethyl-1H-purine-2,6,8(3H)-trione	HMDB
8-Oxocaffeine	HMDB

Chemical Formula

C₈H₁₀N₄O₃

Average Mass

210.1900 Da

Monoisotopic Mass

210.07529 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

7464-93-9

SMILES

CN1C(=O)NC2=C1N(C)C(=O)N(C)C2=O

InChI Identifier

InChI=1S/C8H10N4O3/c1-10-5-4(9-7(10)14)6(13)12(3)8(15)11(5)2/h1-3H3,(H,9,14)

InChI Key

CWENCZHQIWXCCA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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

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	-0.46	ALOGPS
logP	-0.87	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.96 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.32 m³·mol⁻¹	ChemAxon
Polarizability	19.76 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

HMDB0036431

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015318

KNApSAcK ID

Not Available

Chemspider ID

73977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

81972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,3,9-Trimethyluric acid (NP0048504)

MOL for NP0048504 (1,3,9-Trimethyluric acid)

3D MOL for NP0048504 (1,3,9-Trimethyluric acid)

3D SDF for NP0048504 (1,3,9-Trimethyluric acid)

3D-SDF for NP0048504 (1,3,9-Trimethyluric acid)

PDB for NP0048504 (1,3,9-Trimethyluric acid)

3D PDB for NP0048504 (1,3,9-Trimethyluric acid)

SMILES for NP0048504 (1,3,9-Trimethyluric acid)

INCHI for NP0048504 (1,3,9-Trimethyluric acid)

Structure for NP0048504 (1,3,9-Trimethyluric acid)

3D Structure for NP0048504 (1,3,9-Trimethyluric acid)