Livestock Metabolome Database: Showing metabocard for Hypoxanthine (LMDB00067)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:39 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00067

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hypoxanthine

Description

Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Hypoxanthine is a moderately basic compound (based on its pKa). Hypoxanthine exists in all living species, ranging from bacteria to humans. Within humans, hypoxanthine participates in a number of enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, hypoxanthine and phosphoribosyl pyrophosphate can be biosynthesized from inosinic acid; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, hypoxanthine is involved in purine metabolism. Outside of the human body, Hypoxanthine is found, on average, in the highest concentration within beers and milk (cow). Hypoxanthine has also been detected, but not quantified in, several different foods, such as pigeon pea, green vegetables, lovages, gram beans, and arrowhead. This could make hypoxanthine a potential biomarker for the consumption of these foods. Hypoxanthine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6(1H)-Purinone	ChEBI
6-Oxopurine	ChEBI
9H-Purin-6(1H)-one	ChEBI
Hyp	ChEBI
Purin-6(1H)-one	ChEBI
Purine-6-ol	ChEBI
1,7-Dihydro-6H-purin-6-one	HMDB
1,7-Dihydro-6H-purine-6-one	HMDB
1H,7H-Hypoxanthine	HMDB
3H-Purin-6-ol	HMDB
4-Hydroxy-1H-purine	HMDB
6-Hydroxy-1H-purine	HMDB
6-Hydroxypurine	HMDB
7H-Purin-6-ol	HMDB
9H-Purin-6-ol	HMDB
Hypoxanthine enol	HMDB
Purin-6(3H)-one	HMDB
Purin-6-ol	HMDB
Sarcine	HMDB
Sarkin	HMDB
Sarkine	HMDB

Chemical Formula

C₅H₄N₄O

Average Molecular Weight

136.1115

Monoisotopic Molecular Weight

136.03851077

IUPAC Name

7H-purin-6-ol

Traditional Name

6-hydroxypurine

CAS Registry Number

68-94-0

SMILES

OC1=NC=NC2=C1NC=N2

InChI Identifier

InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

FDGQSTZJBFJUBT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. 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

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Pyrimidone
Pyrimidine
Azole
Imidazole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:17368 )
nucleobase analogue (CHEBI:17368 )
purine nucleobase (CHEBI:17368 )
Purine alkaloids (C00262 )
a purine-related compound (HYPOXANTHINE )
a purine base (HYPOXANTHINE )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.55	ALOGPS
logP	-0.048	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	1.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.5 m³·mol⁻¹	ChemAxon
Polarizability	11.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0159-3970000000-0d844fae4a1ffe158823	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-1790000000-ae93bf8bf07b30b65e1a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9340000000-1184c503fb61344c4853	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-3590000000-a419976950afe7934cbc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9800000000-9c266d6963658e9d2cf1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-3970000000-0d844fae4a1ffe158823	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1790000000-ae93bf8bf07b30b65e1a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9340000000-1184c503fb61344c4853	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3590000000-a419976950afe7934cbc	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2890000000-3be4d08be45781881bc1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1590000000-bb6f003bfa7bd04628a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-8900000000-e20eb5d939a2c406a6e2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0613-5900000000-be0624b928ba71cc797d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-2b36c20acd9973b317f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0api-9800000000-fb4e3cccb7d27d119feb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0aor-9200000000-33c2f9eedf9a878530be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-000i-9800000000-9c266d6963658e9d2cf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0910000000-4da64abddc3ac8ab573a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-1900000000-859f61101b12be0b2978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-1900000000-f5d899e7988568d5bcab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-e19e6d04568d3560eb4a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0910000000-8def0d2ec82152826763	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-2900000000-a8361951a2f702a217c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3f653a7c81b328e46cb5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0080290000-be98ce43421dbf9007fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0930030000-56ea204dcb077bc174c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-9000000000-4c2d1980f9e5e4b720a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0900000000-26b3c93bc9dea5a88032	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-1900000000-c367cd4c23aea0f74ecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000l-8900000000-91e35cdcc11d357119f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9100000000-4fb8f4ee2d35aa874617	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014l-9000000000-7934b3037f39d69fc40a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-9000000000-ad93e267446292bf247b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-9000000000-4b8f9e13ed7adf0888c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-9000000000-f295755f591e27bb9f07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014i-9000000000-aee48a44f42a4b767844	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-9000000000-f5ebd92e86cf00f28cf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-9a1ad1aa2d8fb621b608	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-8900000000-ebf57ea530a2d4e31ffa	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Colostrum
Kidney
Kidney perfusate
Liver
Meat
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1159.7 +/- 135.04 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	1254.6 +/- 88.57 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	1497.99 +/- 57.51 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	678.18 +/- 58.48 uM	Not Available	Bovine	20831251	details
Ruminal Fluid	Detected and Quantified	87.9 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	134 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	219 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	220 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Ruminal Fluid	Detected and Quantified	52.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	76.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	85.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	205 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	111 +/- 33 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	205 +/- 61 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	63 +/- 25 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	63 +/- 25 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	80 +/- 24 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	90 +/- 49 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	4.6522 +/- 1.2012 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.0748 +/- 4.9421 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.0812 +/- 3.028 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.86 +/- 7.75 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	7.2952 +/- 4.042 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.1114 +/- 7.5441 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7196 +/- 3.9626 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.88 +/- 11.0975 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.3469 +/- 1.2571 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.2909 +/- 6.876 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.6284 +/- 3.7127 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.4017 +/- 1.1879 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.292 +/- 3.268 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.4621 +/- 1.1569 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.5274 +/- 7.5936 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.6949 +/- 1.3224 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.4752 +/- 2.2358 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.5465 +/- 3.2758 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.2859 +/- 2.9542 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7666 +/- 2.1838 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.2888 +/- 1.9052 uM	Normal	Ovine	Goldansaz et al.,...	details