Livestock Metabolome Database: Showing metabocard for Adenine (LMDB00011)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:25 UTC

Update Date

2016-07-20 21:02:59 UTC

Lmdb

LMDB00011

Secondary Accession Numbers

None

Metabolite 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.

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

135.1267

Monoisotopic Molecular Weight

135.054495185

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

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	-0.38	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-03di-3490000000-7efe9518c90307a43707	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03di-2690000000-6dc072eb8483a2c38e18	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9350000000-220125189c286547e86c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03di-4690000000-2d327a6944df53411886	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0006-3920000000-f488e8aa64272a07b3d9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-000i-0329000000-0b012fa483ce8764d2af	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-3490000000-7efe9518c90307a43707	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-2690000000-6dc072eb8483a2c38e18	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9350000000-220125189c286547e86c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-4690000000-2d327a6944df53411886	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-3920000000-f488e8aa64272a07b3d9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-0329000000-0b012fa483ce8764d2af	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-2690000000-534edabc8ab24e32f3f5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-9700000000-e85c2b0bb19cf3401e5a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-b24b09629456779d96e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-80808f34c7497219d349	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-b24b09629456779d96e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-80808f34c7497219d349	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-cbe0a995dab473351f43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-bfc42d662f222a7c16c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-4900000000-099ee82fc2f658e1cd04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-c100f5ac716c497996be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-379c5c6ea7b1135677c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-346f2325bf2e66e7a339	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-87f60041335919c4a0de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-a71034da1c65738b37bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-090d369100e8edeb5145	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-a56b3bd296195086b5d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-a76f7f2350e82c676371	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-053r-0900000000-4213d2fff3cdad674b8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-0900000000-d0f2f3ccc46d430b6c3c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-bf20f302482d1cc4a27d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-3900000000-f4155217d6bcdbbcc17f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-066u-9400000000-ada6d909e20e2184a05b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-95d4894082ada0b24773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-5900000000-66b1c086d7a666b2d02b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-6900000000-39944576233751576a91	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Kidney perfusate
Meat
Milk
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details

External Links

DrugBank ID

DB00173

HMDB ID

HMDB0000034

FooDB ID

FDB012266

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001490

BiGG ID

34039

BioCyc ID

ADENINE

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rolfes RJ: Regulation of purine nucleotide biosynthesis: in yeast and beyond. Biochem Soc Trans. 2006 Nov;34(Pt 5):786-90. [17052198 ]
Simoni RE, Gomes LN, Scalco FB, Oliveira CP, Aquino Neto FR, de Oliveira ML: Uric acid changes in urine and plasma: an effective tool in screening for purine inborn errors of metabolism and other pathological conditions. J Inherit Metab Dis. 2007 Jun;30(3):295-309. Epub 2007 May 19. [17520339 ]

Showing metabocard for Adenine (LMDB00011)

Structure for LMDB00011 (Adenine)