Cannabis Compound Database: Showing Compound Card for 3,7-Dimethyluric acid (CDB005295)

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Record Information

Version

1.0

Created at

2020-04-17 19:28:51 UTC

Updated at

2020-12-07 19:11:54 UTC

CannabisDB ID

CDB005295

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

3,7-Dimethyluric acid

Description

3,7-Dimethyluric acid, also known as 3,7-dimethylate or 3,7-DMU, 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. An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by methyl groups at N-3 and N-7. 3,7-Dimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,7-Dimethyluric acid exists in all living organisms, ranging from bacteria to humans. 3,7-dimethyluric acid can be biosynthesized from theobromine through the action of the enzyme xanthine dehydrogenase/oxidase. In humans, 3,7-dimethyluric acid is involved in caffeine metabolism. 3,7-Dimethyluric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,7-Dimethylate	Generator
3,7-Dimethylic acid	Generator
37-Dimethyluric acid	ChEMBL, HMDB
37-Dimethylate	Generator, HMDB
37-Dimethylic acid	Generator, HMDB
3,7-Dimethyl-2,6,8-trihydroxypurine	HMDB
3,7-Dimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione	HMDB
3,7-DMU	MeSH, HMDB

Chemical Formula

C₇H₈N₄O₃

Average Molecular Weight

196.16

Monoisotopic Molecular Weight

196.0596

IUPAC Name

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

Traditional Name

3,7-dimethyluric acid

CAS Registry Number

13087-49-5

SMILES

CN1C(=O)NC2=C1C(=O)NC(=O)N2C

InChI Identifier

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

InChI Key

HMLZLHKHNBLLJD-UHFFFAOYSA-N

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

oxopurine (CHEBI:68531 )
Purine alkaloids (C16360 )
a small molecule (CPD-12482 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Biological role:

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	-1.33	GASPARI,F & BONATI,M (1987)

Predicted Properties

Property	Value	Source
logP	-0.61	ALOGPS
logP	-1.1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.13	ChemAxon
pKa (Strongest Basic)	-6	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	17.69 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3,7-Dimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0v0a-0900000000-46adc1bd1a2829ed3eab	Spectrum
Predicted GC-MS	3,7-Dimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-5554059238ba6f5a4aa7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001l-9800000000-bcef3be559d5d3540d62	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-7d225864dafe7484ef17	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-81b25f479c4f1663781d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-0900000000-0f875011e8751037af3f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-ddcf3e38bdc4d7198abc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-f9c0039adcc98c79f10d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0900000000-5398ccddcd1ad6de4811	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-79381deb2ab0e04daf89	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-0e499ff6f23e328dc54a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-c0e1ff53101ddbba850d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-a0758f9ce9eb83d7a97d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-8ba3918ee48755b0ba1a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2900000000-a5948ea7307823697f8e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-82b93be35cae293c6cab	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Caffeine Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Xanthine dehydrogenase/oxidase	XDH	2p23.1	P47989	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Xanthine dehydrogenase/oxidase	XDH	2p23.1	P47989	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001982

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022780

KNApSAcK ID

Not Available

Chemspider ID

74994

KEGG Compound ID

C16360

BioCyc ID

CPD-12482

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83126

PDB ID

Not Available

ChEBI ID

68531

References

General References

Not Available

Enzymes

Enzyme Details

1. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

Showing Compound Card for 3,7-Dimethyluric acid (CDB005295)

Structure for CDB005295 (3,7-Dimethyluric acid)

Enzymes