Showing Compound Tetrahydrobiopterin (FDB021880)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:26 UTC

Update date

2015-07-21 06:56:49 UTC

Primary ID

FDB021880

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tetrahydrobiopterin

Description

Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. A defect in BH4 production and/or a defect in the enzyme dihydropteridine reductase (DHPR) causes phenylketonuria type IV, as well as dopa-responsive dystonias. -- Wikipedia. [HMDB]

CAS Number

17528-72-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(1R,2S)-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-Pteridinyl)-1,2-propandiol	HMDB
(1R,2S)-(2-Amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiol	hmdb
1-Butanone, 1-(2,4,5-trihydroxyphenyl)	MeSH, HMDB
2',4',5'-Trihydroxybutyrophenone	MeSH, HMDB
2,4,5-Trihydroxybutyrophenone	MeSH, HMDB
2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone	HMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-5,6,7,8-Tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone	hmdb
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone	ChEBI
2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone	ChEBI
2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone	HMDB

Showing 1 to 10 of 40 entries

Predicted Properties

Property	Value	Source
Water Solubility	2.21 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	3.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	132 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	23.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H15N5O3

IUPAC name

2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one

InChI Identifier

InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)

InChI Key

FNKQXYHWGSIFBK-UHFFFAOYSA-N

Isomeric SMILES

CC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2

Average Molecular Weight

241.2471

Monoisotopic Molecular Weight

241.117489371

Classification

Description

Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Pyrimidine
1,3-aminoalcohol
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
1,2-diol
1,2-aminoalcohol
Secondary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydropterin (CHEBI:15372 )
biopterins (CHEBI:15372 )
a biopterin (TETRA-H-BIOPTERIN )

Ontology

Myocardial infarction

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

All tissues

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Tetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-5900000000-804847492ab49a9a85fc	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-8095000000-47f102cc1afbed04012f	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydrobiopterin, TBDMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-241111b39335d9a7d02d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bl-0980000000-a6b56555596f17eb9943	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01dj-1900000000-337483f746fd21c54572	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0290000000-5db8572d378da978b669	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-0930000000-4e48e429709976699df9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-8474626666ad84477dd8	2017-09-01	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15372

Phenol-Explorer ID

Not Available

DrugBank ID

DB00360

HMDB ID

HMDB00027

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34464

KNApSAcK ID

Not Available

HET ID

1DF1

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Tetrahydrobiopterin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Phenylalanine-4-hydroxylase	PAH	P00439
Pterin-4-alpha-carbinolamine dehydratase	PCBD1	P61457
Sepiapterin reductase	SPR	P35270
Tryptophan 5-hydroxylase 1	TPH1	P17752
Tryptophan 5-hydroxylase 2	TPH2	Q8IWU9
Tyrosine 3-monooxygenase	TH	P07101