Cannabis Compound Database: Showing Compound Card for Adenine (CDB004787)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8)transporters (2) Show 11 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:36:44 UTC

Updated at

2020-12-07 19:10:56 UTC

CannabisDB ID

CDB004787

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Adenine

Description

Adenine, also known as 6-aminopurine or Ade, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenine is a strong basic compound (based on its pKa). Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. Adenine exists in all living species, ranging from bacteria to humans. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. In humans, adenine is involved in riboflavin metabolism. Adenine is a potentially toxic compound. Adenine (sometimes known as vitamin B4) combines with the sugar ribose to form adenosine, which in turn can be bonded with from one to three phosphoric acid units, yielding AMP, ADP and ATP . A modified form of adenosine monophosphate (cyclic AMP) is an imporant secondary messenger in the propagation of many hormonal stimuli. Adenine is an integral part of the structure of many coenzymes. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. Certain SVTs can be successfully terminated with adenosine. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. These adenine derivatives perform important functions in cellular metabolism. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), which drives many cellular metabolic processes by transferring chemical energy between reactions. Adenine 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
6-Aminopurine	ChEBI
A	ChEBI
Ade	ChEBI
Adenin	ChEBI
Leucon	Kegg
1,6-Dihydro-6-iminopurine	HMDB
1H-Purin-6-amine	HMDB
1H-Purine-6-amine	HMDB
3,6-Dihydro-6-iminopurine	HMDB
6-Amino-1H-purine	HMDB
6-Amino-3H-purine	HMDB
6-Amino-7H-purine	HMDB
6-Amino-9H-purine	HMDB
6-Amino-purine	HMDB
9H-Purin-6-amine	HMDB
9H-Purin-6-yl-amin	HMDB
9H-Purin-6-ylamine	HMDB
9H-Purine-6-amine	HMDB
Adeninimine	HMDB
Vitamin b4	HMDB
Vitamin b 4	HMDB
4, Vitamin b	HMDB
b 4, Vitamin	HMDB

Chemical Formula

C₅H₅N₅

Average Molecular Weight

135.13

Monoisotopic Molecular Weight

135.0545

IUPAC Name

7H-purin-6-amine

Traditional Name

vitamin B4

CAS Registry Number

73-24-5

SMILES

NC1=C2NC=NC2=NC=N1

InChI Identifier

InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)

InChI Key

GFFGJBXGBJISGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
Imidolactam
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

6-aminopurines (CHEBI:16708 )
purine nucleobase (CHEBI:16708 )
purines (C00147 )
a ring (ADENINE-RING )

Ontology

Tuberculous meningitis

Infections and infestations:

Meningitis

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Biological role:

Metabolite

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.03 mg/mL	Not Available
logP	-0.09	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.38	ALOGPS
logP	-0.57	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	3.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.22 m³·mol⁻¹	ChemAxon
Polarizability	12.29 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000i-6900000000-39944576233751576a91	2014-09-20	View Spectrum
GC-MS	Adenine, 2 TMS, GC-MS Spectrum	splash10-03di-3490000000-7efe9518c90307a43707	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-03di-2690000000-6dc072eb8483a2c38e18	Spectrum
GC-MS	Adenine, 2 TMS, GC-MS Spectrum	splash10-00di-9350000000-220125189c286547e86c	Spectrum
GC-MS	Adenine, 2 TMS, GC-MS Spectrum	splash10-03di-4690000000-2d327a6944df53411886	Spectrum
GC-MS	Adenine, 1 TMS, GC-MS Spectrum	splash10-0006-3920000000-f488e8aa64272a07b3d9	Spectrum
GC-MS	Adenine, 3 TMS, GC-MS Spectrum	splash10-000i-0329000000-0b012fa483ce8764d2af	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-03di-3490000000-7efe9518c90307a43707	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-03di-2690000000-6dc072eb8483a2c38e18	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-00di-9350000000-220125189c286547e86c	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-03di-4690000000-2d327a6944df53411886	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-0006-3920000000-f488e8aa64272a07b3d9	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-000i-0329000000-0b012fa483ce8764d2af	Spectrum
GC-MS	Adenine, non-derivatized, GC-MS Spectrum	splash10-03di-2690000000-534edabc8ab24e32f3f5	Spectrum
Predicted GC-MS	Adenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a5i-9700000000-e85c2b0bb19cf3401e5a	Spectrum
Predicted GC-MS	Adenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-b24b09629456779d96e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-80808f34c7497219d349	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-b24b09629456779d96e6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-80808f34c7497219d349	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-cbe0a995dab473351f43	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-bfc42d662f222a7c16c7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-4900000000-099ee82fc2f658e1cd04	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-c100f5ac716c497996be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-379c5c6ea7b1135677c6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-346f2325bf2e66e7a339	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-87f60041335919c4a0de	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-a71034da1c65738b37bd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-090d369100e8edeb5145	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-a56b3bd296195086b5d0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-a76f7f2350e82c676371	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-053r-0900000000-4213d2fff3cdad674b8e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-0900000000-d0f2f3ccc46d430b6c3c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-bf20f302482d1cc4a27d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-3900000000-f4155217d6bcdbbcc17f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-066u-9400000000-ada6d909e20e2184a05b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-95d4894082ada0b24773	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-5900000000-66b1c086d7a666b2d02b	2012-07-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, 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, 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	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Xanthine dehydrogenase/oxidase	XDH	2p23.1	P47989	details
S-methyl-5'-thioadenosine phosphorylase	MTAP	9p21	Q13126	details
Adenine phosphoribosyltransferase	APRT	16q24	P07741	details
Hypoxanthine-guanine phosphoribosyltransferase	HPRT1	Xq26.1	P00492	details
Peroxisomal trans-2-enoyl-CoA reductase	PECR	2q35	Q9BY49	details
Equilibrative nucleoside transporter 2	SLC29A2	11q13	Q14542	details
Equilibrative nucleoside transporter 3	SLC29A3	10q22.1	Q9BZD2	details
Purine nucleoside phosphorylase	PNP	14q13.1	P00491	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Equilibrative nucleoside transporter 2	SLC29A2	11q13	Q14542	details
Equilibrative nucleoside transporter 3	SLC29A3	10q22.1	Q9BZD2	details

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

HMDB0000034

DrugBank ID

DB00173

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

190

PDB ID

Not Available

ChEBI ID

16708

References

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show All

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

Enzyme Details

2. S-methyl-5'-thioadenosine phosphorylase

General function:: Involved in transferase activity, transferring pentosyl groups
Specific function:: Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:: MTAP
Uniprot ID:: Q13126
Molecular weight:: 31235.76

Enzyme Details

3. Adenine phosphoribosyltransferase

General function:: Involved in adenine phosphoribosyltransferase activity
Specific function:: Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:: APRT
Uniprot ID:: P07741
Molecular weight:: 19607.535

Enzyme Details

4. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Enzyme Details

5. Peroxisomal trans-2-enoyl-CoA reductase

General function:: Involved in regulation of apoptosis
Specific function:: Participates in chain elongation of fatty acids. Has no 2,4-dienoyl-CoA reductase activity.
Gene Name:: PECR
Uniprot ID:: Q9BY49
Molecular weight:: 32544.11

Enzyme Details

6. Equilibrative nucleoside transporter 2

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:: SLC29A2
Uniprot ID:: Q14542
Molecular weight:: 50112.3

Enzyme Details

7. Equilibrative nucleoside transporter 3

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). Mediates transport of adenine, adenosine and uridine, as well as several nucleoside analog drugs, such as anticancer and antiviral agents, including cladribine, cordycepin, tubercidin and AZT. Does not transport hypoxanthine
Gene Name:: SLC29A3
Uniprot ID:: Q9BZD2
Molecular weight:: 51799.9

Enzyme Details

8. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Transporters

Enzyme Details

1. Equilibrative nucleoside transporter 2

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:: SLC29A2
Uniprot ID:: Q14542
Molecular weight:: 50112.3

Enzyme Details

2. Equilibrative nucleoside transporter 3

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). Mediates transport of adenine, adenosine and uridine, as well as several nucleoside analog drugs, such as anticancer and antiviral agents, including cladribine, cordycepin, tubercidin and AZT. Does not transport hypoxanthine
Gene Name:: SLC29A3
Uniprot ID:: Q9BZD2
Molecular weight:: 51799.9

Only showing the first 10 proteins. There are 11 proteins in total.

Show All

Showing Compound Card for Adenine (CDB004787)

Structure for CDB004787 (Adenine)

Enzymes

Transporters