MiMeDB: Showing metabocard for Pterin (MMDBc0000776)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:41 UTC

Update Date

2024-04-30 19:33:39 UTC

Metabolite ID

MMDBc0000776

Metabolite Identification

Common Name

Pterin

Description

Pterin is a chemical compound composed of a pyrazine ring and a pyrimidine ring; the pyrimidine ring has a carbonyl oxygen and an amino group. Several tautomers of pterin exist and are shown below. Pterin belongs to the pteridine family of heterocycles. -- Wikipedia .

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Pyridinoline.mol                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      -0.667  -2.310   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.334  -2.310   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -2.001   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.667   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.001   0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.334   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334  -1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.001  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.667  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    1                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
2-Amino-4-hydroxypteridine	ChEBI
2-Amino-4-oxopteridine	Kegg
2-Amino-1H-pteridin-4-one	HMDB
2-Amino-3H-pteridin-4-one	HMDB
2-Amino-4(1H)-pteridinone	HMDB
2-Amino-4(3H)-pteridinone	HMDB
2-Amino-4-pteridinol	HMDB
2-Amino-4-pteridone	HMDB
2-Amino-quinonoid dihydropterin	HMDB
2-Aminopteridin-4-one	HMDB
4-oxo-2-Aminopteridine	HMDB
4-Oxopterin	HMDB
Pteridoxamine	HMDB
Pterine	HMDB
2-Amino-4-hydroxyaminopteridine	HMDB
AHAPT	HMDB

Molecular Formula

C₆H₅N₅O

Average Mass

163.1368

Monoisotopic Mass

163.049409807

IUPAC Name

2-amino-3,4-dihydropteridin-4-one

Traditional Name

2-amino-4-oxopteridine

CAS Registry Number

Not Available

SMILES

NC1=NC2=NC=CN=C2C(=O)N1

InChI Identifier

InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12)

InChI Key

HNXQXTQTPAJEJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterin (CHEBI:44992 )
a pterin (2-AMINO-4-HYDROXYPTERIDINE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-0.96	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.82 m³·mol⁻¹	ChemAxon
Polarizability	14.46 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3900000000-e0c5aa11edc5408b2afd	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-815f9d4247cb9067f9fb	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014l-5900000000-6bd37ba7d9f26d33ffd5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9100000000-b809a46cbde852be02de	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-0900000000-71eab96d7f1dfed51963	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1900000000-36d14ee4f35692f07bee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0900000000-7d6238777a46df27af01	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9000000000-289c0930b78dd1447e10	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-066r-4900000000-8c47f8f3ca753ec1cf6f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9300000000-938f26c8bed8f1edc185	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-ca751d8c09c98e0c9d3d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0900000000-a67b522aa27e6f75f46e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ad3fade684bdebfb41e3	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-f1eb4d0b367f209bc766	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-a250d1c9d32e286b29f6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9300000000-190579d7d5ba6d0c14c5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-4005b83e558e2b0c5772	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-a4698cb941c94fd08799	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-8ed28777d0de229aa6a3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-99937f8026369fb0e183	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-2900000000-41450f7664125a38cc97	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-5a06c4c35a067e936a16	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-0dba7b98ddf974fcc10c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-ba39f053d7d33e17ee00	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-7334fbd934d9e46491f7	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Epidermis
Feces
Fibroblasts
Liver

Tissue Locations

Epidermis
Fibroblasts
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191831	Methionine synthase	Unknown	Q99707	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	1	Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Glycine max	FooDB	DUKE

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Epidermis	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

2-AMINO-4-HYDROXYPTERIDINE

BiGG ID

Not Available

Wikipedia Link

Pterin

METLIN ID

5766

PubChem Compound

73000

PDB ID

Not Available

ChEBI ID

18265

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Krumdieck CL, Fukushima K, Fukushima T, Shiota T, Butterworth CE Jr: A long-term study of the excretion of folate and pterins in a human subject after ingestion of 14C folic acid, with observations on the effect of diphenylhydantoin administration. Am J Clin Nutr. 1978 Jan;31(1):88-93. doi: 10.1093/ajcn/31.1.88. [PubMed:413430 ]
Dhondt JL, Tilmont P, Ringel J, Farriaux JP: Pterins analysis in amniotic fluid for the prenatal diagnosis of GTP cyclohydrolase deficiency. J Inherit Metab Dis. 1990;13(6):879-82. doi: 10.1007/BF01800213. [PubMed:2079836 ]
Katoh S, Sueoka T, Matsuura S, Sugimoto T: Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. doi: 10.1016/0024-3205(89)90240-3. [PubMed:2615555 ]
Beckman JS, Parks DA, Pearson JD, Marshall PA, Freeman BA: A sensitive fluorometric assay for measuring xanthine dehydrogenase and oxidase in tissues. Free Radic Biol Med. 1989;6(6):607-15. doi: 10.1016/0891-5849(89)90068-3. [PubMed:2753392 ]
Dhondt JL, Cotton RG, Danks DM: Liver enzyme activities in hyperphenylalaninaemia due to a defective synthesis of tetrahydrobiopterin. J Inherit Metab Dis. 1985;8(2):47-8. doi: 10.1007/BF01801660. [PubMed:3939528 ]
Gordon JH, Perry KO: Pre- and postsynaptic neurochemical alterations following estrogen-induced striatal dopamine hypo- and hypersensitivity. Brain Res Bull. 1983 Apr;10(4):425-8. doi: 10.1016/0361-9230(83)90137-5. [PubMed:6134572 ]
Kaufman S, Kapatos G, Rizzo WB, Schulman JD, Tamarkin L, Van Loon GR: Tetrahydropterin therapy for hyperphenylalaninemia caused by defective synthesis of tetrahydrobiopterin. Ann Neurol. 1983 Sep;14(3):308-15. doi: 10.1002/ana.410140309. [PubMed:6139056 ]
Niederwieser A, Blau N, Wang M, Joller P, Atares M, Cardesa-Garcia J: GTP cyclohydrolase I deficiency, a new enzyme defect causing hyperphenylalaninemia with neopterin, biopterin, dopamine, and serotonin deficiencies and muscular hypotonia. Eur J Pediatr. 1984 Feb;141(4):208-14. doi: 10.1007/BF00572762. [PubMed:6734669 ]
Blau N, Kierat L, Matasovic A, Leimbacher W, Heizmann CW, Guardamagna O, Ponzone A: Antenatal diagnosis of tetrahydrobiopterin deficiency by quantification of pterins in amniotic fluid and enzyme activity in fetal and extrafetal tissue. Clin Chim Acta. 1994 May;226(2):159-69. doi: 10.1016/0009-8981(94)90213-5. [PubMed:7923811 ]
Stupperich E: Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol Rev. 1993 Nov;12(4):349-65. doi: 10.1111/j.1574-6976.1993.tb00027.x. [PubMed:8268006 ]
Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Yamakita J, Nasako Y, Hiroishi K, Higashino K: Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):395-400. doi: 10.1016/0378-4347(96)00071-0. [PubMed:8811453 ]
Han F, Huynh BH, Shi H, Lin B, Ma Y: Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1999 Apr 1;71(7):1265-9. doi: 10.1021/ac981218v. [PubMed:10204031 ]
Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. [PubMed:11238300 ]
Bonafe L, Thony B, Penzien JM, Czarnecki B, Blau N: Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. Am J Hum Genet. 2001 Aug;69(2):269-77. doi: 10.1086/321970. Epub 2001 Jul 6. [PubMed:11443547 ]
Rokos H, Beazley WD, Schallreuter KU: Oxidative stress in vitiligo: photo-oxidation of pterins produces H(2)O(2) and pterin-6-carboxylic acid. Biochem Biophys Res Commun. 2002 Apr 12;292(4):805-11. doi: 10.1006/bbrc.2002.6727. [PubMed:11944885 ]

Showing metabocard for Pterin (MMDBc0000776)

MOL for #<Metabolite:0x0000556b6afddc40>

3D MOL for #<Metabolite:0x0000556b6afddc40>

3D SDF for #<Metabolite:0x0000556b6afddc40>

3D-SDF for #<Metabolite:0x0000556b6afddc40>

PDB for #<Metabolite:0x0000556b6afddc40>

3D PDB for #<Metabolite:0x0000556b6afddc40>

SMILES for #<Metabolite:0x0000556b6afddc40>

INCHI for #<Metabolite:0x0000556b6afddc40>

Structure for #<Metabolite:0x0000556b6afddc40>

3D Structure for #<Metabolite:0x0000556b6afddc40>