Bovine Metabolome Database: Showing metabocard for Tetrahydrobiopterin (BMDB0000027)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:39 UTC

Update Date

2020-05-21 16:29:04 UTC

BMDB ID

BMDB0000027

Secondary Accession Numbers

BMDB0000787
BMDB00027
BMDB00787

Metabolite Identification

Common Name

Tetrahydrobiopterin

Description

L-erythro-tetrahydrobiopterin, also known as 5,6,7,8-tetrahydrobiopterin or 6R-BH4, 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. L-erythro-tetrahydrobiopterin is a drug which is used for the treatment of tetrahydrobiopterin (bh4) deficiency. L-erythro-tetrahydrobiopterin exists in all living organisms, ranging from bacteria to humans. In cattle, L-erythro-tetrahydrobiopterin is involved in the metabolic pathway called the phenylalanine and tyrosine metabolism pathway. Based on a literature review a significant number of articles have been published on L-erythro-tetrahydrobiopterin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone	ChEBI
(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin	ChEBI
(6R)-L-Erythro-tetrahydrobiopterin	ChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone	ChEBI
5,6,7,8-Tetrahydrobiopterin	ChEBI
6R-5,6,7,8-Tetrahydrobiopterin	ChEBI
6R-BH4	ChEBI
6R-L-5,6,7,8-Tetrahydrobiopterin	ChEBI
R-THBP	ChEBI
Sapropterina	ChEBI
Sapropterinum	ChEBI
Tetrahydrobiopterin	ChEBI
5,6,7,8-erythro-Tetrahydrobiopterin	MeSH, HMDB
5,6,7,8-tetrahydro-L-Erythrobiopterin	MeSH, HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r,s))-isomer	MeSH, HMDB
5,6,7,8-Tetrahydrodictyopterin	MeSH, HMDB
6R-L-erythro-5,6,7,8-Tetrahydrobiopterin	MeSH, HMDB
BPH4	MeSH, HMDB
D-threo-Tetrahydrobiopterin	MeSH, HMDB
THBP	MeSH, HMDB
Kuvan	MeSH, HMDB
Phenylalanine hydroxylase cofactor	MeSH, HMDB
Sapropterin dihydrochloride	MeSH, HMDB
tetrahydro-6-Biopterin	MeSH, HMDB
2',4',5'-Trihydroxybutyrophenone	MeSH
Sapropterin	MeSH
Trihydroxybutyrophenone	MeSH
1-Butanone, 1-(2,4,5-trihydroxyphenyl)	MeSH
2,4,5-Trihydroxybutyrophenone	MeSH
(6R)-5,6,7,8-Tetrahydro-L-biopterin	HMDB
(6R)-5,6,7,8-Tetrahydrobiopterin	HMDB
(6R)-Tetrahydrobiopterin	HMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone	HMDB
6R-Tetrahydro-L-biopterin	HMDB
6beta-5,6,7,8-Tetrahydro-L-biopterin	HMDB
6β-5,6,7,8-Tetrahydro-L-biopterin	HMDB
L-erythro-Tetrahydrobiopterin	HMDB
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone	HMDB

Chemical Formula

C₉H₁₅N₅O₃

Average Molecular Weight

241.2471

Monoisotopic Molecular Weight

241.117489371

IUPAC Name

(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

Traditional Name

tetrahydrobiopterin

CAS Registry Number

17528-72-2

SMILES

[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O

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)/t3-,4+,6-/m0/s1

InChI Key

FNKQXYHWGSIFBK-RPDRRWSUSA-N

Chemical Taxonomy

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

5,6,7,8-tetrahydrobiopterin (CHEBI:59560 )
Coenzymes (C00272 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria
Nucleus

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	250 - 255 °C (hydrochloride salt)	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	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	1.58	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	23.67 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
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9810000000-1bfd11724596b460cae9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-014i-6945000000-07faa91218e86d3bfe0d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0006-0290000000-cd4c8c11b8279075b00a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0006-0390000000-35dddce9e2df2a9ac198	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0006-0590000000-cda875209a034e44cbe1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00kf-0980000000-53721c484501c528e7a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-014l-0930000000-533fabd35a8c5ca7830e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-014i-0910000000-580c038db540047891c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-014i-0910000000-8d6b754dadadb6330906	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0006-0090000000-f21b677255493f1f2d1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-014i-0900000000-5c1b60d0d7ea4dd4dbff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-014i-1900000000-6f22457ab99b14bb653e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014i-1900000000-cd0410f4da61716c7f9e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014i-2900000000-d4f18a979b6d07e83a63	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0002-0900000000-87174b78444828c3b52d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0a4i-0900000000-dc272a476d306f26c722	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-ae19513d01a0046ed2e8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-004i-0900000000-d4a52489d35bde573bd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0f79-0900000000-af02b0d9eb8f6577afb8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-c2259602e8f1fd522fd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0006-0090000000-c88ed5ea9e11715bc275	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-e6b01d1139ccb3c6338d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gi3-0980000000-8963ef41f1138b05a813	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-1900000000-bcfa359703563c696c0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-4810efa20f31adea3824	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006y-1930000000-5b32feeb643e238bb159	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-a7dbebeb1df4ea110948	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Nucleus

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arginine and Proline Metabolism		Not Available
Tyrosine Metabolism		Not Available
Tryptophan Metabolism		Not Available
Pterine Biosynthesis		Not Available
Ion Channels and Their Functional Role in Vascular Endothelium		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0059658

DrugBank ID

DB00360

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

40270

KEGG Compound ID

C00272

BioCyc ID

CPD-14053

BiGG ID

Not Available

Wikipedia Link

Sapropterin

METLIN ID

Not Available

PubChem Compound

44257

PDB ID

Not Available

ChEBI ID

59560

References

Synthesis Reference

Steven S. Gross, "Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis." U.S. Patent US5502050, issued October, 1984.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Nitric oxide synthase, endothelial

General function:: Inorganic ion transport and metabolism
Specific function:: Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.
Gene Name:: NOS3
Uniprot ID:: P29473
Molecular weight:: 133287.0

Enzyme Details

2. Nitric oxide synthase, inducible

General function:: Inorganic ion transport and metabolism
Specific function:: Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM. Involved in inflammation, enhances the synthesis of proinflammatory mediators such as IL6 and IL8.
Gene Name:: NOS2
Uniprot ID:: Q27995
Molecular weight:: 131208.0

Enzyme Details

3. Sepiapterin reductase

General function:: Lipid transport and metabolism
Specific function:: Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:: SPR
Uniprot ID:: Q17QK8
Molecular weight:: 28939.0

Reactions

6-Lactoyltetrahydropterin + NADP → Tetrahydrobiopterin + NADPH	details

Enzyme Details

4. Tyrosine 3-monooxygenase

General function:: Amino acid transport and metabolism
Specific function:: Plays an important role in the physiology of adrenergic neurons.
Gene Name:: TH
Uniprot ID:: P17289
Molecular weight:: 55123.0

Enzyme Details

5. Phenylalanine-4-hydroxylase

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the hydroxylation of L-phenylalanine to L-tyrosine.
Gene Name:: PAH
Uniprot ID:: Q2KIH7
Molecular weight:: 51727.0

Enzyme Details

6. Inducible nitric oxid synthase

General function:: Involved in arginine binding
Specific function:: Not Available
Gene Name:: iNOS
Uniprot ID:: Q6ZXD5
Molecular weight:: 12093.0

Enzyme Details

7. Dihydropteridine reductase

General function:: Lipid transport and metabolism
Specific function:: The product of this enzyme, tetrahydrobiopterin (BH-4), is an essential cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases.
Gene Name:: QDPR
Uniprot ID:: Q3T0Z7
Molecular weight:: 25504.0

Reactions

Tetrahydrobiopterin + NADP → Dihydrobiopterin + NADPH	details

Enzyme Details

8. Dihydrofolate reductase

General function:: Coenzyme transport and metabolism
Specific function:: Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFR2 (By similarity).
Gene Name:: DHFR
Uniprot ID:: P00376
Molecular weight:: 21604.0

Reactions

7,8-Dihydroneopterin + NADPH → NADP + Tetrahydrobiopterin + Water	details

Showing metabocard for Tetrahydrobiopterin (BMDB0000027)

Structure for BMDB0000027 (Tetrahydrobiopterin)

Enzymes

Reactions

Reactions

Reactions