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Record Information

Version

2.0

Creation Date

2015-09-08 17:49:54 -0600

Update Date

2015-09-08 17:49:54 -0600

Secondary Accession Numbers

ECMDB24177

Identification

Name:

L-erythro-tetrahydrobiopterin

Description

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

Weight:

Average: 241.2471
Monoisotopic: 241.117489371

InChI Key:

FNKQXYHWGSIFBK-RPDRRWSUSA-N

InChI:

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

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

tetrahydrobiopterin

SMILES:

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

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 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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)	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

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	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	59560
HMDB ID	HMDB0059658
Pubchem Compound ID	44257
Kegg ID	C00272
ChemSpider ID	40270
Wikipedia ID	Sapropterin
BioCyc ID	Not Available

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

L-erythro-tetrahydrobiopterin (M2MDB006294)

Structure for #<Compound:0xae938470>