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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:48 UTC

HMDB ID

HMDB0000403

Secondary Accession Numbers

HMDB00403

Metabolite Identification

Common Name

2-Hydroxyadenine

Description

2-Hydroxyadenine, also known as 2-OH-ade or isoguanine, 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. 2-Hydroxyadenine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-hydroxyadenine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Hydroxyadenine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Oxoadenine	ChEBI
6-Amino-1,3-dihydro-2H-purin-2-one	ChEBI
6-Amino-3,7-dihydro-purin-2-one	ChEBI
6-Amino-3,9-dihydro-2H-purin-2-one	ChEBI
6-Amino-7H-purin-2-ol	ChEBI
6-Amino-9H-purin-2-ol	ChEBI
2-Hydroxy-6-aminopurine	HMDB
2-Oxyadenine	HMDB
6-Amino-2-hydroxypurine	HMDB
6-Amino-3,7(9)-dihydro-purin-2-one	HMDB
Isoguanine	HMDB
2-OH-Ade	HMDB
Crotonoside	HMDB
2-Hydroxyadenine	ChEBI

Chemical Formula

C₅H₅N₅O

Average Molecular Weight

151.1261

Monoisotopic Molecular Weight

151.049409807

IUPAC Name

6-amino-7H-purin-2-ol

Traditional Name

2-hydroxy-6-aminopurine

CAS Registry Number

3373-53-3

SMILES

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

InChI Identifier

InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)

InChI Key

DRAVOWXCEBXPTN-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
Hydroxypyrimidine
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:62462 )
a small molecule (CPD0-2461 )

Ontology

Not Available

Urine (PMID: 19309105)

Cellular substructure

Cytoplasm (HMDB: HMDB0000403)

Source

Endogenous

Endogenous (HMDB: HMDB0000403)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.062 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	121.039	30932474
[M+H]+	MetCCS_train_pos	126.979	30932474
[M-H]-	Not Available	121.039	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000323
[M+H]+	Not Available	126.944	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000323

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.06 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	2.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.71 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.15 m³·mol⁻¹	ChemAxon
Polarizability	13.36 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]+	130.478	31661259
DarkChem	[M-H]-	130.292	31661259
AllCCS	[M+H]+	132.831	32859911
AllCCS	[M-H]-	126.227	32859911
DeepCCS	[M+H]+	130.507	30932474
DeepCCS	[M-H]-	127.725	30932474
DeepCCS	[M-2H]-	164.576	30932474
DeepCCS	[M+Na]+	139.48	30932474
AllCCS	[M+H]+	132.8	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	127.1	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.27 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6579 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	143.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	475.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	370.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	46.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	252.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	252.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	475.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	629.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	47.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	637.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	618.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	240.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyadenine	NC1=NC(O)=NC2=C1NC=N2	2833.7	Standard polar	33892256
2-Hydroxyadenine	NC1=NC(O)=NC2=C1NC=N2	2091.2	Standard non polar	33892256
2-Hydroxyadenine	NC1=NC(O)=NC2=C1NC=N2	1918.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyadenine,1TMS,isomer #1	C[Si](C)(C)OC1=NC(N)=C2[NH]C=NC2=N1	2019.2	Semi standard non polar	33892256
2-Hydroxyadenine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C=N2	2196.1	Semi standard non polar	33892256
2-Hydroxyadenine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=NC(O)=NC(N)=C21	2089.7	Semi standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C=N2	2053.7	Semi standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C=N2	2079.9	Standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1[NH]C=N2	3114.7	Standard polar	33892256
2-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C	2097.0	Semi standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C	2017.9	Standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C	2778.8	Standard polar	33892256
2-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C	2119.4	Semi standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C	2143.8	Standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C	2843.2	Standard polar	33892256
2-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2	2183.1	Semi standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2	2061.1	Standard non polar	33892256
2-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2	2683.7	Standard polar	33892256
2-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C=NC2=N1	2029.2	Semi standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C=NC2=N1	2137.1	Standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]C=NC2=N1	2698.5	Standard polar	33892256
2-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	2111.2	Semi standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	2006.2	Standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	2677.6	Standard polar	33892256
2-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C	2128.3	Semi standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C	2196.1	Standard non polar	33892256
2-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C	2457.0	Standard polar	33892256
2-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=CN2[Si](C)(C)C	2106.8	Semi standard non polar	33892256
2-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=CN2[Si](C)(C)C	2127.9	Standard non polar	33892256
2-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C(=N1)N=CN2[Si](C)(C)C	2421.8	Standard polar	33892256
2-Hydroxyadenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2[NH]C=NC2=N1	2280.3	Semi standard non polar	33892256
2-Hydroxyadenine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1[NH]C=N2	2403.6	Semi standard non polar	33892256
2-Hydroxyadenine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=NC(O)=NC(N)=C21	2359.7	Semi standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	2482.1	Semi standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	2439.3	Standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(O[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	3148.0	Standard polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2497.1	Semi standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2377.3	Standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(N)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2842.2	Standard polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C	2541.4	Semi standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C	2568.4	Standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C	2850.8	Standard polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	2612.2	Semi standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	2458.7	Standard non polar	33892256
2-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	2754.6	Standard polar	33892256
2-Hydroxyadenine,3TBDMS,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=NC2=N1	2580.1	Semi standard non polar	33892256
2-Hydroxyadenine,3TBDMS,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=NC2=N1	2755.1	Standard non polar	33892256
2-Hydroxyadenine,3TBDMS,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=NC2=N1	2815.1	Standard polar	33892256
2-Hydroxyadenine,3TBDMS,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=N2	2680.3	Semi standard non polar	33892256
2-Hydroxyadenine,3TBDMS,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=N2	2629.2	Standard non polar	33892256
2-Hydroxyadenine,3TBDMS,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=N2	2821.9	Standard polar	33892256
2-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C	2744.5	Semi standard non polar	33892256
2-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C	2783.7	Standard non polar	33892256
2-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C	2666.6	Standard polar	33892256
2-Hydroxyadenine,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)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2831.0	Semi standard non polar	33892256
2-Hydroxyadenine,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)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2925.6	Standard non polar	33892256
2-Hydroxyadenine,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)=C2C(=N1)N=CN2[Si](C)(C)C(C)(C)C	2743.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1900000000-c16950878c62efe1b98d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (1 TMS) - 70eV, Positive	splash10-0kmi-7930000000-f60855003c167d5a6142	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyadenine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyadenine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-42af2345f291c0931747	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyadenine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-053r-2900000000-20dc64d93a8160bc7cba	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyadenine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0kai-9200000000-dd4e5a7f42bbde9a7362	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 10V, Positive-QTOF	splash10-0udi-0900000000-20dd242c9f0be41ca3b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 20V, Positive-QTOF	splash10-0udi-0900000000-0a5cc033a455487be201	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 40V, Positive-QTOF	splash10-0a59-9700000000-88fd5f0f4ed191155fca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 10V, Negative-QTOF	splash10-0udi-0900000000-db76d46c9a9e58708daf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 20V, Negative-QTOF	splash10-0pb9-1900000000-2c2e928303dd65e7b74a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 40V, Negative-QTOF	splash10-001l-9100000000-cba052229db1704e3934	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 10V, Positive-QTOF	splash10-0udi-0900000000-361a2474138028086bb3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 20V, Positive-QTOF	splash10-0udi-0900000000-c0348939b06d3f4c02ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 40V, Positive-QTOF	splash10-0a4i-9400000000-23cc92eaf9fad62612b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 10V, Negative-QTOF	splash10-0udi-0900000000-21c3d82f91283a8a49e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 20V, Negative-QTOF	splash10-0udi-2900000000-abe3ac9c0f2bdc1aff6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyadenine 40V, Negative-QTOF	splash10-0006-9100000000-3ba35f09b305bcf5a6cd	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	<1 nmol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

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

FDB022019

KNApSAcK ID

C00050937

Chemspider ID

69351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoguanine

METLIN ID

5392

PubChem Compound

76900

PDB ID

Not Available

ChEBI ID

62462

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hayashi, Taketo; Tamato, Toyomochi. Preparation of isoguanine. Jpn. Kokai Tokkyo Koho (1994), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Olinski R, Zastawny T, Budzbon J, Skokowski J, Zegarski W, Dizdaroglu M: DNA base modifications in chromatin of human cancerous tissues. FEBS Lett. 1992 Sep 7;309(2):193-8. [PubMed:1324197 ]
Arashidani K, Iwamoto-Tanaka N, Muraoka M, Kasai H: Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100. Mutat Res. 1998 Jul 17;403(1-2):223-7. [PubMed:9726022 ]

Showing metabocard for 2-Hydroxyadenine (HMDB0000403)

MOL for HMDB0000403 (2-Hydroxyadenine)

3D MOL for HMDB0000403 (2-Hydroxyadenine)

3D SDF for HMDB0000403 (2-Hydroxyadenine)

3D-SDF for HMDB0000403 (2-Hydroxyadenine)

PDB for HMDB0000403 (2-Hydroxyadenine)

3D PDB for HMDB0000403 (2-Hydroxyadenine)

SMILES for HMDB0000403 (2-Hydroxyadenine)

INCHI for HMDB0000403 (2-Hydroxyadenine)

Structure for HMDB0000403 (2-Hydroxyadenine)

3D Structure for HMDB0000403 (2-Hydroxyadenine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra