Cannabis Compound Database: Showing Compound Card for Paraxanthine (CDB005291)

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Record Information

Version

1.0

Created at

2020-04-17 19:28:27 UTC

Updated at

2020-12-07 19:11:54 UTC

CannabisDB ID

CDB005291

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Paraxanthine

Description

Paraxanthine, also known as p-xanthine, 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. A dimethylxanthine having the two methyl groups located at positions 1 and 7. Paraxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Paraxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, paraxanthine participates in a number of enzymatic reactions. In particular, paraxanthine and formaldehyde can be biosynthesized from caffeine through the action of the enzyme cytochrome P450 1A2. In addition, paraxanthine and acetyl-CoA can be converted into 5-acetylamino-6-formylamino-3-methyluracil; which is catalyzed by the enzyme arylamine N-acetyltransferase 2. In humans, paraxanthine is involved in caffeine metabolism. Paraxanthine 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-Dihydro-1,7-dimethyl-1H-purine-2,6-dione	ChEBI
p-Xanthine	ChEBI
1,7-Dimethyl-xanthine	HMDB
1,7-Dimethylxanthine	HMDB, MeSH

Chemical Formula

C₇H₈N₄O₂

Average Molecular Weight

180.16

Monoisotopic Molecular Weight

180.0647

IUPAC Name

1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

paraxanthine

CAS Registry Number

611-59-6

SMILES

CN1C=NC2=C1C(=O)N(C)C(=O)N2

InChI Identifier

InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)

InChI Key

QUNWUDVFRNGTCO-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
Hydroxypyrimidine
N-substituted imidazole
Pyrimidine
Imidazole
Azole
Heteroaromatic compound
Lactam
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethylxanthine (CHEBI:25858 )
Purine alkaloids (C13747 )
a small molecule (1-7-DIMETHYLXANTHINE )

Ontology

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	351 - 352 °C	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	-0.63	ALOGPS
logP	0.24	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.76	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.72 m³·mol⁻¹	ChemAxon
Polarizability	16.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Paraxanthine, non-derivatized, GC-MS Spectrum	splash10-000i-2980000000-6ee5dc3100885f205536	Spectrum
GC-MS	Paraxanthine, non-derivatized, GC-MS Spectrum	splash10-000i-2980000000-6ee5dc3100885f205536	Spectrum
Predicted GC-MS	Paraxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uka-3900000000-d979badf45de391835d4	Spectrum
Predicted GC-MS	Paraxanthine, 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)	splash10-001i-0900000000-2d1aa5f80618f452686c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-0900000000-3326bcbee23b63dcc230	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-9824aef9dc2f13c24bcc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00e9-1900000000-9d0dde13bb1ce13e2644	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00fr-0900000000-1aa733a1b7e41b994d8d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00di-1900000000-190ff3302e9f5a37a72f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00fr-0900000000-1aa733a1b7e41b994d8d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0900000000-729a2bed81ba15260ffa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0900000000-18d0a9c63a1dfb683c9b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-c52421f0ba1f46241853	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-00di-0900000000-0bd6ed3d764e5a9b374e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00e9-1900000000-9d0dde13bb1ce13e2644	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0w29-0940000000-127f99d8e7324e01eb66	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0ik9-0930000000-fe234438cbe3be0b30f6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-1900000000-190ff3302e9f5a37a72f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0900000000-d6040ea84fe19d8c5cc6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-935e5a47dc1abe7b1196	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-3900000000-2f3998477ce19f3ff96f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4900000000-c89111b73e8a9a163111	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-5e7c398698bb5c16617d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-522eaddc21ef92e70e62	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9200000000-d10a1141c0e21f56ec00	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-bc2d3cb520a4fcb81529	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-e2e2992ce9b1265af790	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05am-9300000000-e1aefedceb8692ffe91f	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 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
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
Arylamine N-acetyltransferase 1	NAT1	8p22	P18440	details
Arylamine N-acetyltransferase 2	NAT2	8p22	P11245	details
Xanthine dehydrogenase/oxidase	XDH	2p23.1	P47989	details
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	15q24.1	A0N0X8	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Xanthine dehydrogenase/oxidase	XDH	2p23.1	P47989	details
Cytochrome P450 3A4	CYP3A4	7q21.1	P08684	details
Cytochrome P450 2C9	CYP2C9	10q24	P11712	details
Cytochrome P450 2C19	CYP2C19	10q24	P33261	details
Cytochrome P450 2E1	CYP2E1	10q24.3-qter	P05181	details
Cytochrome P450 3A43	CYP3A43	7q21.1	Q9HB55	details
Cytochrome P450 1B1	CYP1B1	2p22.2	Q16678	details
Cytochrome P450 2C18	CYP2C18	10q24	P33260	details
Cytochrome P450 2F1	CYP2F1	19q13.2	P24903	details
Cytochrome P450 4X1	CYP4X1	1	Q8N118	details
Cytochrome P450 2B6	CYP2B6	19q13.2	P20813	details
Cytochrome P450 3A5	CYP3A5	7q21.1	P20815	details
Cytochrome P450 2A13	CYP2A13	19q13.2	Q16696	details
Cytochrome P450 3A7	CYP3A7	7q21-q22.1	P24462	details
Cytochrome P450 4B1	CYP4B1	1p34-p12	P13584	details
Cytochrome P450 4Z1	CYP4Z1	1p33	Q86W10	details
Cytochrome P450 1A2	CYP1A2	15q24.1	P05177	details
Cytochrome P450 19A1	CYP19A1	15q21.1	P11511	details
Cytochrome P450 2C8	CYP2C8	10q23.33	P10632	details
Cytochrome P450 2S1	CYP2S1	19q13.1	Q96SQ9	details
Cytochrome P450 2J2	CYP2J2	1p31.3-p31.2	P51589	details
Cytochrome P450 2A7	CYP2A7	19q13.2	P20853	details
Cytochrome P450 2A6	CYP2A6	19q13.2	P11509	details
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	15q24.1	A0N0X8	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001860

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Paraxanthine

METLIN ID

1457

PubChem Compound

4687

PDB ID

Not Available

ChEBI ID

25858

References

General References

Not Available

Only showing the first 10 proteins. There are 28 proteins in total.

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Enzymes

Enzyme Details

1. Arylamine N-acetyltransferase 1

General function:: Involved in acetyltransferase activity
Specific function:: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:: NAT1
Uniprot ID:: P18440
Molecular weight:: 33898.445

Enzyme Details

2. Arylamine N-acetyltransferase 2

General function:: Involved in acetyltransferase activity
Specific function:: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:: NAT2
Uniprot ID:: P11245
Molecular weight:: 33570.245

Enzyme Details

3. 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

Enzyme Details

4. Cytochrome P450, family 1, subfamily A, polypeptide 1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP1A1
Uniprot ID:: A0N0X8
Molecular weight:: 58164.8

Only showing the first 10 proteins. There are 28 proteins in total.

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Showing Compound Card for Paraxanthine (CDB005291)

Structure for CDB005291 (Paraxanthine)

Enzymes