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Showing metabocard for Adenine (HMDB0000034)

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enzymes (8) Show 8 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:28 UTC
HMDB IDHMDB0000034
Secondary Accession Numbers
  • HMDB00034
Metabolite Identification
Common NameAdenine
DescriptionAdenine, 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
Data?1676999668
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000034 (Adenine)

173
  Mrv1652309032023502D          

 10 11  0  0  0  0            999 V2000
    3.8596    0.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.2043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  2  0  0  0  0
  3  7  2  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0000034 (Adenine)

HMDB0000034
     RDKit          3D
Adenine
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.2697   -1.9082   -0.0459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -0.5074    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793    0.3958    0.1730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    1.7219    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967    2.1524    0.1937 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542    1.2972    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793    1.4393   -0.0298 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    0.2454   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -0.6694   -0.1555 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063   -0.0543   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1782   -2.2309   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -2.6371    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    2.4213    0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.0370   -0.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -1.7029   -0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
 10  6  2  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0000034 (Adenine)

173
  Mrv1652309032023502D          

 10 11  0  0  0  0            999 V2000
    3.8596    0.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.2043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  2  0  0  0  0
  3  7  2  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000034

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C5H5N5

> <MOLECULAR_WEIGHT>
135.1267

> <EXACT_MASS>
135.054495185

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.291219062634639

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7H-purin-6-amine

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-0.5734702306666666

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.29343639321823

> <JCHEM_PKA_STRONGEST_BASIC>
3.6393051728406145

> <JCHEM_POLAR_SURFACE_AREA>
80.48

> <JCHEM_REFRACTIVITY>
38.2195

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin B4

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000034 (Adenine)

HMDB0000034
     RDKit          3D
Adenine
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.2697   -1.9082   -0.0459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -0.5074    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793    0.3958    0.1730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    1.7219    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967    2.1524    0.1937 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542    1.2972    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793    1.4393   -0.0298 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    0.2454   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -0.6694   -0.1555 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063   -0.0543   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1782   -2.2309   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -2.6371    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    2.4213    0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.0370   -0.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -1.7029   -0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
 10  6  2  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0000034 (Adenine)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 173                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  N   UNK     0       7.205   0.231   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.205  -2.248   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.414  -2.549   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.080  -0.239   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414   2.071   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.747  -0.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.103  -1.009   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.779   0.000  0.00  0.00           C+0
CONECT    1    6    9                                                       
CONECT    2    7    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    8                                                            
CONECT    6    1    7    8                                                  
CONECT    7    2    3    6                                                  
CONECT    8    4    5    6                                                  
CONECT    9    1    2                                                       
CONECT   10    3    4                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0000034 (Adenine)

COMPND    HMDB0000034
HETATM    1  N1  UNL     1      -1.270  -1.908  -0.046  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.998  -0.507   0.036  1.00  0.00           C  
HETATM    3  N2  UNL     1      -1.979   0.396   0.173  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.769   1.722   0.254  1.00  0.00           C  
HETATM    5  N3  UNL     1      -0.497   2.152   0.194  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.554   1.297   0.056  1.00  0.00           C  
HETATM    7  N4  UNL     1       1.879   1.439  -0.030  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.479   0.245  -0.160  1.00  0.00           C  
HETATM    9  N5  UNL     1       1.495  -0.669  -0.156  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.306  -0.054  -0.025  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.178  -2.231  -0.447  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.600  -2.637   0.277  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.604   2.421   0.366  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.557   0.037  -0.253  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.624  -1.703  -0.240  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3   10
CONECT    3    4
CONECT    4    5    5   13
CONECT    5    6
CONECT    6    7   10   10
CONECT    7    8    8
CONECT    8    9   14
CONECT    9   10   15
END
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SMILES for HMDB0000034 (Adenine)

NC1=C2NC=NC2=NC=N1
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INCHI for HMDB0000034 (Adenine)

InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
6-AminopurineChEBI
AChEBI
AdeChEBI
AdeninChEBI
LeuconKegg
1,6-Dihydro-6-iminopurineHMDB
1H-Purin-6-amineHMDB
1H-Purine-6-amineHMDB
3,6-Dihydro-6-iminopurineHMDB
6-Amino-1H-purineHMDB
6-Amino-3H-purineHMDB
6-Amino-7H-purineHMDB
6-Amino-9H-purineHMDB
6-Amino-purineHMDB
9H-Purin-6-amineHMDB
9H-Purin-6-yl-aminHMDB
9H-Purin-6-ylamineHMDB
9H-Purine-6-amineHMDB
AdeninimineHMDB
Vitamin b4HMDB
Vitamin b 4HMDB
4, Vitamin bHMDB
b 4, VitaminHMDB
Chemical FormulaC5H5N5
Average Molecular Weight135.1267
Monoisotopic Molecular Weight135.054495185
IUPAC Name7H-purin-6-amine
Traditional Namevitamin B4
CAS Registry Number73-24-5
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 KeyGFFGJBXGBJISGV-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.03 mg/mLNot Available
LogP-0.09HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg118.330932474
[M-H]-Baker122.330932474
[M-H]-MetCCS_test_neg117.830932474
[M+H]+Astarita_pos119.330932474
[M+H]+Baker127.930932474
[M+H]+MetCCS_test_pos125.07830932474
[M-H]-Not Available120.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000364
[M+H]+Not Available126.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000364
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)3.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.25931661259
DarkChem[M-H]-123.15331661259
AllCCS[M+H]+128.78132859911
AllCCS[M-H]-121.94332859911
DeepCCS[M+H]+120.82630932474
DeepCCS[M-H]-116.98230932474
DeepCCS[M-2H]-154.47230932474
DeepCCS[M+Na]+129.61230932474
AllCCS[M+H]+128.832859911
AllCCS[M+H-H2O]+124.032859911
AllCCS[M+NH4]+133.332859911
AllCCS[M+Na]+134.632859911
AllCCS[M-H]-121.932859911
AllCCS[M+Na-2H]-123.232859911
AllCCS[M+HCOO]-124.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AdenineNC1=C2NC=NC2=NC=N12377.3Standard polar33892256
AdenineNC1=C2NC=NC2=NC=N11713.9Standard non polar33892256
AdenineNC1=C2NC=NC2=NC=N11827.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adenine,1TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C=N21933.0Semi standard non polar33892256
Adenine,1TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C=N21796.1Standard non polar33892256
Adenine,1TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C=N22924.8Standard polar33892256
Adenine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=NC=NC(N)=C211870.7Semi standard non polar33892256
Adenine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=NC=NC(N)=C211757.9Standard non polar33892256
Adenine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=NC=NC(N)=C212680.3Standard polar33892256
Adenine,2TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C1864.6Semi standard non polar33892256
Adenine,2TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C1887.7Standard non polar33892256
Adenine,2TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C2578.7Standard polar33892256
Adenine,2TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C=N21941.3Semi standard non polar33892256
Adenine,2TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C=N21790.1Standard non polar33892256
Adenine,2TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C=N22569.4Standard polar33892256
Adenine,3TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C1902.4Semi standard non polar33892256
Adenine,3TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C1901.4Standard non polar33892256
Adenine,3TMS,isomer #1C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C2294.0Standard polar33892256
Adenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C=N22155.8Semi standard non polar33892256
Adenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C=N21950.7Standard non polar33892256
Adenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C=N23016.4Standard polar33892256
Adenine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC(N)=C212123.8Semi standard non polar33892256
Adenine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC(N)=C211938.3Standard non polar33892256
Adenine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC(N)=C212772.8Standard polar33892256
Adenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C2259.5Semi standard non polar33892256
Adenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C2296.3Standard non polar33892256
Adenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C2653.8Standard polar33892256
Adenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22352.6Semi standard non polar33892256
Adenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22198.6Standard non polar33892256
Adenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22684.7Standard polar33892256
Adenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2486.1Semi standard non polar33892256
Adenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2535.4Standard non polar33892256
Adenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2528.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-03di-3490000000-7efe9518c90307a437072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e182014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9350000000-220125189c286547e86c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (2 TMS)splash10-03di-4690000000-2d327a6944df534118862014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (1 TMS)splash10-0006-3920000000-f488e8aa64272a07b3d92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (3 TMS)splash10-000i-0329000000-0b012fa483ce8764d2af2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Non-derivatized)splash10-03di-3490000000-7efe9518c90307a437072017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Non-derivatized)splash10-00di-9350000000-220125189c286547e86c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (Non-derivatized)splash10-03di-4690000000-2d327a6944df534118862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (Non-derivatized)splash10-0006-3920000000-f488e8aa64272a07b3d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-MS (Non-derivatized)splash10-000i-0329000000-0b012fa483ce8764d2af2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Adenine GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-534edabc8ab24e32f3f52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-9700000000-e85c2b0bb19cf3401e5a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-6900000000-39944576233751576a912014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0900000000-b24b09629456779d96e62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-001i-0900000000-80808f34c7497219d3492012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-b24b09629456779d96e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-QTOF , negative-QTOFsplash10-001i-0900000000-80808f34c7497219d3492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine LC-ESI-QTOF , negative-QTOFsplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine , negative-QTOFsplash10-001i-0900000000-cbe0a995dab473351f432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine , negative-QTOFsplash10-001i-0900000000-bfc42d662f222a7c16c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 20V, Negative-QTOFsplash10-0a59-4900000000-099ee82fc2f658e1cd042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 10V, Negative-QTOFsplash10-001i-0900000000-c100f5ac716c497996be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 35V, Negative-QTOFsplash10-001i-0900000000-379c5c6ea7b1135677c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 40V, Negative-QTOFsplash10-014i-9000000000-346f2325bf2e66e7a3392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 35V, Negative-QTOFsplash10-001i-0900000000-87f60041335919c4a0de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 40V, Negative-QTOFsplash10-014l-9000000000-a71034da1c65738b37bd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 30V, Negative-QTOFsplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 10V, Negative-QTOFsplash10-001i-0900000000-090d369100e8edeb51452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 35V, Negative-QTOFsplash10-001i-0900000000-a56b3bd296195086b5d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 10V, Negative-QTOFsplash10-001i-0900000000-a76f7f2350e82c6763712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 35V, Negative-QTOFsplash10-053r-0900000000-4213d2fff3cdad674b8e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 20V, Negative-QTOFsplash10-0a59-0900000000-d0f2f3ccc46d430b6c3c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 40V, Negative-QTOFsplash10-0a4i-0900000000-bf20f302482d1cc4a27d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 20V, Negative-QTOFsplash10-0a59-3900000000-f4155217d6bcdbbcc17f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine 30V, Negative-QTOFsplash10-066u-9400000000-ada6d909e20e2184a05b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0900000000-95d4894082ada0b247732012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adenine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-5900000000-66b1c086d7a666b2d02b2012-07-24HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.3 +/- 0.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.64 +/- 0.15 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.2 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified1.19 +/- 1.25 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified0.448 +/- 0.309 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified1.15 +/- 0.93 uMAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.65 (0.52-0.85) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified2.9 (1.4-5.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0-6 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified1.17 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
 details
UrineDetected and Quantified4.087 +/- 1.149 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified<0.1 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified13-20 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 +/- 0.3 uMAdult (>18 years old)BothSolid tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0 - 18.0) uMChildren (1-13 years old)Not Specified
Meningitis		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 (0 - 23.4) uMChildren (1-13 years old)Not SpecifiedTuberculous meningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.96 (0 - 12.0) uMChildren (1-13 years old)Not Specified
Meningitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected and Quantified1.03 +/- 0.73 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified0.87 +/- 0.78 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified0.37 +/- 0.21 uMAdult (>18 years old)BothLewy body disease details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer		 details
UrineDetected and Quantified7.163 +/- 7.025 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Thymidine treatment
  1. Leyva A, Schornagel JH, Kraal I, Wadman SK, Pinedo HM: Clinical and biochemical studies of high-dose thymidine treatment in patients with solid tumors. J Cancer Res Clin Oncol. 1984;107(3):211-6. [PubMed:6736109 ]
Meningitis
  1. Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Neuron-specific enolase, nucleotides, nucleosides, purine bases, oxypurines and uric acid concentrations in cerebrospinal fluid of children with meningitis. Brain Dev. 2003 Mar;25(2):102-6. [PubMed:12581805 ]
Tuberculous meningitis
  1. Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Neuron-specific enolase, nucleotides, nucleosides, purine bases, oxypurines and uric acid concentrations in cerebrospinal fluid of children with meningitis. Brain Dev. 2003 Mar;25(2):102-6. [PubMed:12581805 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB00173
Phenol Explorer Compound IDNot Available
FooDB IDFDB012266
KNApSAcK IDC00001490
Chemspider ID185
KEGG Compound IDC00147
BioCyc IDADENINE
BiGG ID34039
Wikipedia LinkAdenine
METLIN ID85
PubChem Compound190
PDB IDNot Available
ChEBI ID16708
Food Biomarker OntologyNot Available
VMH IDADE
MarkerDB IDMDB00000017
Good Scents IDNot Available
References
Synthesis ReferenceBaddiley, J.; Lythgoe, B.; Todd, A. R. Synthesis of purine nucleosides. II. A new and convenient synthesis of adenine. Journal of the Chemical Society (1943), 386-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Di Pietro V, Perruzza I, Amorini AM, Balducci A, Ceccarelli L, Lazzarino G, Barsotti P, Giardina B, Tavazzi B: Clinical, biochemical and molecular diagnosis of a compound homozygote for the 254 bp deletion-8 bp insertion of the APRT gene suffering from severe renal failure. Clin Biochem. 2007 Jan;40(1-2):73-80. Epub 2006 Oct 19. [PubMed:17126311 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
  4. Moriyama H, Iizuka T, Nagai M, Hoshi K: Adenine, an inhibitor of platelet aggregation, from the leaves of Cassia alata. Biol Pharm Bull. 2003 Sep;26(9):1361-4. [PubMed:12951489 ]
  5. Liu Y, Xu G, Xu C, Garcia L, Lin CC, Yeh LT: Ultra sensitive method for the determination of 9-(2-phosphonylmethoxyethyl)adenine in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 25;803(2):293-8. [PubMed:15063338 ]
  6. Terry KL, De Vivo I, Titus-Ernstoff L, Shih MC, Cramer DW: Androgen receptor cytosine, adenine, guanine repeats, and haplotypes in relation to ovarian cancer risk. Cancer Res. 2005 Jul 1;65(13):5974-81. [PubMed:15994977 ]
  7. Steiner MC, Evans R, Deacon SJ, Singh SJ, Patel P, Fox J, Greenhaff PL, Morgan MD: Adenine nucleotide loss in the skeletal muscles during exercise in chronic obstructive pulmonary disease. Thorax. 2005 Nov;60(11):932-6. Epub 2005 Jul 29. [PubMed:16055624 ]
  8. Whitehead JW, Lee GP, Gharagozloo P, Hofer P, Gehrig A, Wintergerst P, Smyth D, McCoull W, Hachicha M, Patel A, Kyle DJ: 8-Substituted analogues of 3-(3-cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-adenine: highly potent and selective PDE4 inhibitors. J Med Chem. 2005 Feb 24;48(4):1237-43. [PubMed:15715490 ]
  9. Reimers HJ, Packham MA, Mustard JF: Labeling of the releasable adenine nucleotides of washed human platelets. Blood. 1977 Jan;49(1):89-99. [PubMed:401462 ]
  10. Hartmann S, Okun JG, Schmidt C, Langhans CD, Garbade SF, Burgard P, Haas D, Sass JO, Nyhan WL, Hoffmann GF: Comprehensive detection of disorders of purine and pyrimidine metabolism by HPLC with electrospray ionization tandem mass spectrometry. Clin Chem. 2006 Jun;52(6):1127-37. Epub 2006 Apr 13. [PubMed:16613999 ]
  11. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  12. Ruiz-Stewart I, Kazerounian S, Pitari GM, Schulz S, Waldman SA: Soluble guanylate cyclase is allosterically inhibited by direct interaction with 2-substituted adenine nucleotides. Eur J Biochem. 2002 Apr;269(8):2186-93. [PubMed:11985597 ]
  13. Rolfes RJ: Regulation of purine nucleotide biosynthesis: in yeast and beyond. Biochem Soc Trans. 2006 Nov;34(Pt 5):786-90. [PubMed:17052198 ]
  14. 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. [PubMed:17520339 ]
  15. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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
References
  1. Bouzidi H, Lacour B, Daudon M: [2,8-dihydroxyadenine nephrolithiasis: from diagnosis to therapy]. Ann Biol Clin (Paris). 2007 Nov-Dec;65(6):585-92. [PubMed:18039602 ]
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
Reactions
5'-Methylthioadenosine + Phosphate → Adenine + 5-Methylthioribose 1-phosphatedetails
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
Reactions
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
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
Reactions
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
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
Reactions
Adenosine + Phosphate → Adenine + Ribose 1-phosphatedetails
Deoxyadenosine + Phosphate → Adenine + Deoxyribose 1-phosphatedetails