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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:47 UTC

HMDB ID

HMDB0000401

Secondary Accession Numbers

HMDB00401

Metabolite Identification

Common Name

2,8-Dihydroxyadenine

Description

2,8-Dihydroxyadenine is a Purine metabolite usually not detectable in biofluids of normal individuals; this insoluble metabolite (at physiological urinary pH) cause urinary tract calculi and arthritis, and is identified in Adenine phosphoribosyltransferase deficiency (APRT, OMIM 102600 ). (PMID 16613999 ) In APRT, 2,8-dihydroxyadenine (DHA) accumulates in crystals within the tubular lumens (a feature of many kidney stone diseases) creating crystal-induced injury in human kidney epithelial cells. (PMID 16374038 ) Urinary DHA crystals are easily recognized under a microscope, and effective treatment can be offered and therefore the prognosis depends upon the renal function at diagnosis; treatment consists of adequate fluid intake, a low-purine diet and administration of allopurinol. (PMID 15764278 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2,8-Dihydroxyadenine.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       2.622   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.622  -1.540   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.288  -2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.046  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.046   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.288   0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.288   2.310   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -1.510  -2.016   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.415  -0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.510   0.476   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -3.955  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.955  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    1                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6R)-2,6-2,8-Dihydroxyadenine	HMDB
2,8-Dioxyadenine	HMDB
6-Amino-1H-purine-2,8(3H,7H)-dione	HMDB
6-Amino-2,8-dihydroxypurine	HMDB
6-Amino-7H-purine-2,8-diol	HMDB
6-Amino-purine-2,8-diol	HMDB
Dimethyloctanoate	HMDB
Dimethyloctanoic acid	HMDB
2,8-Dihydroxyadenine	MeSH

Chemical Formula

C₅H₅N₅O₂

Average Molecular Weight

167.1255

Monoisotopic Molecular Weight

167.044324429

IUPAC Name

6-amino-7H-purine-2,8-diol

Traditional Name

6-amino-2,8-dihydroxypurine

CAS Registry Number

30377-37-8

SMILES

NC1=NC(O)=NC2=C1NC(O)=N2

InChI Identifier

InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12)

InChI Key

XFBOJHLYDJZYSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. 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

Purinones

Alternative Parents

Substituents

6-aminopurine
Purinone
Aminopyrimidine
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000401)

Source

Endogenous

Endogenous (HMDB: HMDB0000401)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.002 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.11 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	0.18	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	0.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.94 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.6 m³·mol⁻¹	ChemAxon
Polarizability	14.54 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.224	31661259
DarkChem	[M-H]-	135.284	31661259
AllCCS	[M+H]+	136.666	32859911
AllCCS	[M-H]-	130.285	32859911
DeepCCS	[M+H]+	135.102	30932474
DeepCCS	[M-H]-	132.087	30932474
DeepCCS	[M-2H]-	168.771	30932474
DeepCCS	[M+Na]+	144.309	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.2	32859911
AllCCS	[M+NH4]+	140.8	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	130.3	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	131.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,8-Dihydroxyadenine	NC1=NC(O)=NC2=C1NC(O)=N2	3117.7	Standard polar	33892256
2,8-Dihydroxyadenine	NC1=NC(O)=NC2=C1NC(O)=N2	2560.4	Standard non polar	33892256
2,8-Dihydroxyadenine	NC1=NC(O)=NC2=C1NC(O)=N2	2044.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,8-Dihydroxyadenine,1TMS,isomer #1	C[Si](C)(C)OC1=NC(N)=C2[NH]C(O)=NC2=N1	2267.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TMS,isomer #2	C[Si](C)(C)OC1=NC2=NC(O)=NC(N)=C2[NH]1	2279.2	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TMS,isomer #3	C[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C(O)=N2	2337.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TMS,isomer #4	C[Si](C)(C)N1C(O)=NC2=NC(O)=NC(N)=C21	2266.7	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #1	C[Si](C)(C)OC1=NC(N)=C2[NH]C(O[Si](C)(C)C)=NC2=N1	2190.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C(O)=N2	2288.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #3	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O)N2[Si](C)(C)C	2164.1	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C(O[Si](C)(C)C)=N2	2270.9	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #5	C[Si](C)(C)OC1=NC2=NC(O)=NC(N)=C2N1[Si](C)(C)C	2235.2	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #6	C[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C(O)=N2)[Si](C)(C)C	2326.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TMS,isomer #7	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C(O)=N2	2252.9	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C)=N2	2160.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C)=N2	2091.9	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C)=N2	3093.9	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2152.5	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2060.9	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2899.2	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O)=NC2=N1	2281.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O)=NC2=N1	2239.2	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O)=NC2=N1	2704.7	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #4	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O)=N2	2150.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #4	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O)=N2	2086.9	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #4	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O)=N2	2748.0	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #5	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	2232.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #5	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	2213.3	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #5	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	2717.2	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #6	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2161.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #6	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2129.7	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #6	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2664.0	Standard polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	2231.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	2235.5	Standard non polar	33892256
2,8-Dihydroxyadenine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	2581.7	Standard polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O[Si](C)(C)C)=NC2=N1	2225.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O[Si](C)(C)C)=NC2=N1	2154.4	Standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C(O[Si](C)(C)C)=NC2=N1	2655.5	Standard polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2210.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2105.7	Standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2654.2	Standard polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C	2201.5	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C	2210.2	Standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #3	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C	2516.2	Standard polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #4	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2220.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #4	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2259.3	Standard non polar	33892256
2,8-Dihydroxyadenine,4TMS,isomer #4	C[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2449.0	Standard polar	33892256
2,8-Dihydroxyadenine,5TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2268.9	Semi standard non polar	33892256
2,8-Dihydroxyadenine,5TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2213.7	Standard non polar	33892256
2,8-Dihydroxyadenine,5TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C)N2[Si](C)(C)C	2404.8	Standard polar	33892256
2,8-Dihydroxyadenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2[NH]C(O)=NC2=N1	2506.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N)=C2[NH]1	2507.2	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C(O)=N2	2568.1	Semi standard non polar	33892256
2,8-Dihydroxyadenine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(O)=NC2=NC(O)=NC(N)=C21	2524.9	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2[NH]C(O[Si](C)(C)C(C)(C)C)=NC2=N1	2577.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C(O)=N2	2715.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O)N2[Si](C)(C)C(C)(C)C	2612.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	2676.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N)=C2N1[Si](C)(C)C(C)(C)C	2670.6	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C	2793.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2735.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	2752.3	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	2713.5	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	3150.9	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2717.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2689.8	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2977.7	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O)=NC2=N1	2859.5	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O)=NC2=N1	2842.5	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O)=NC2=N1	2850.1	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2777.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2708.2	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2899.1	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2787.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2835.4	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2857.4	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2813.0	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2758.1	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2826.3	Standard polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2874.1	Semi standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2831.4	Standard non polar	33892256
2,8-Dihydroxyadenine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2794.4	Standard polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O[Si](C)(C)C(C)(C)C)=NC2=N1	2907.7	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O[Si](C)(C)C(C)(C)C)=NC2=N1	2954.0	Standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]C(O[Si](C)(C)C(C)(C)C)=NC2=N1	2918.9	Standard polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2938.4	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2887.7	Standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2939.2	Standard polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C(C)(C)C	2949.9	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C(C)(C)C	2977.8	Standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O)N2[Si](C)(C)C(C)(C)C	2844.9	Standard polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	2951.8	Semi standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	3041.4	Standard non polar	33892256
2,8-Dihydroxyadenine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC2=NC(O)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	2813.7	Standard polar	33892256
2,8-Dihydroxyadenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	3088.5	Semi standard non polar	33892256
2,8-Dihydroxyadenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	3119.8	Standard non polar	33892256
2,8-Dihydroxyadenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C(=N1)N=C(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2848.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-2900000000-2a6ad00e5a61874dafba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (2 TMS) - 70eV, Positive	splash10-006t-5590000000-9a6615b1bb6baa991e39	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Dihydroxyadenine GC-MS (TBDMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 10V, Positive-QTOF	splash10-014i-0900000000-992c36bf805d3bd5b77c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 20V, Positive-QTOF	splash10-0gb9-0900000000-b0d2a41d5894b75e61ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 40V, Positive-QTOF	splash10-0pc3-9500000000-094a0ab08df4cb8d66d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 10V, Negative-QTOF	splash10-014i-0900000000-73c402f938cd3d00ebbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 20V, Negative-QTOF	splash10-00di-2900000000-dfacf0b01ba05bd293a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 40V, Negative-QTOF	splash10-0006-9000000000-56660a79cc117195f3ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 10V, Negative-QTOF	splash10-014i-0900000000-f1c385fcdecbeefa0015	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 20V, Negative-QTOF	splash10-014j-1900000000-926ad02fad1950acf99d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 40V, Negative-QTOF	splash10-0006-9100000000-a310374a286696bca445	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 10V, Positive-QTOF	splash10-014i-0900000000-2907e7cb009d3747cf21	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 20V, Positive-QTOF	splash10-014i-1900000000-623b79f0acf731c6831f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Dihydroxyadenine 40V, Positive-QTOF	splash10-00kb-9200000000-2c1cb7961f2587587a7a	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022018

KNApSAcK ID

Not Available

Chemspider ID

83302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,8-Dihydroxyadenine

METLIN ID

5390

PubChem Compound

92268

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Stevens, Marcus A.; Smith, Herman W.; Brown, George Bosworth. Purine N-oxides. VII. Reaction of aminopurine 1-N-oxides with acetic anhydride. Journal of the American Chemical Society (1960), 82 1148-52.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Roth GJ, Moore GL, Kline WE, Poskitt TR: The renal effect of intravenous adenine in humans. Transfusion. 1975 Mar-Apr;15(2):116-23. [PubMed:1091029 ]
Peck CC, Bailey FJ, Moore GL: Enhanced solubility of 2,8 dihydroxyadenine (DOA) in human urine. Transfusion. 1977 Jul-Aug;17(4):383-90. [PubMed:17934 ]
Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73. [PubMed:878002 ]
Liang L, Chen J, Vittal R, Selvanayagam ZE, McAteer JA, Deng L, Tischfield J, Chin KV, Sahota A: Expression profiling of crystal-induced injury in human kidney epithelial cells. Nephron Physiol. 2006;103(1):p53-62. Epub 2005 Dec 21. [PubMed:16374038 ]
Arnadottir M, Laxdal T, Halldorsdottir B: 2,8-dihydroxyadeninuria: are there no cases in Scandinavia? Scand J Urol Nephrol. 2005;39(1):82-6. [PubMed:15764278 ]

Showing metabocard for 2,8-Dihydroxyadenine (HMDB0000401)

MOL for HMDB0000401 (2,8-Dihydroxyadenine)

3D MOL for HMDB0000401 (2,8-Dihydroxyadenine)

3D SDF for HMDB0000401 (2,8-Dihydroxyadenine)

3D-SDF for HMDB0000401 (2,8-Dihydroxyadenine)

PDB for HMDB0000401 (2,8-Dihydroxyadenine)

3D PDB for HMDB0000401 (2,8-Dihydroxyadenine)

SMILES for HMDB0000401 (2,8-Dihydroxyadenine)

INCHI for HMDB0000401 (2,8-Dihydroxyadenine)

Structure for HMDB0000401 (2,8-Dihydroxyadenine)

3D Structure for HMDB0000401 (2,8-Dihydroxyadenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra