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Record Information
Version2.0
Creation Date2015-09-08 17:49:54 -0600
Update Date2015-09-08 17:49:54 -0600
Secondary Accession Numbers
  • ECMDB24177
Identification
Name:L-erythro-tetrahydrobiopterin
Description
Structure
Thumb
Synonyms:
ValueSource
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneChEBI
(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterinChEBI
(6R)-L-Erythro-tetrahydrobiopterinChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinoneChEBI
5,6,7,8-TetrahydrobiopterinChEBI
6R-5,6,7,8-TetrahydrobiopterinChEBI
6R-BH4ChEBI
6R-L-5,6,7,8-TetrahydrobiopterinChEBI
R-THBPChEBI
SapropterinaChEBI
SapropterinumChEBI
TetrahydrobiopterinChEBI
5,6,7,8-erythro-TetrahydrobiopterinMeSH, HMDB
5,6,7,8-tetrahydro-L-ErythrobiopterinMeSH, HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerMeSH, HMDB
5,6,7,8-TetrahydrodictyopterinMeSH, HMDB
6R-L-erythro-5,6,7,8-TetrahydrobiopterinMeSH, HMDB
BPH4MeSH, HMDB
D-threo-TetrahydrobiopterinMeSH, HMDB
THBPMeSH, HMDB
KuvanMeSH, HMDB
Phenylalanine hydroxylase cofactorMeSH, HMDB
Sapropterin dihydrochlorideMeSH, HMDB
tetrahydro-6-BiopterinMeSH, HMDB
2',4',5'-TrihydroxybutyrophenoneMeSH
SapropterinMeSH
TrihydroxybutyrophenoneMeSH
1-Butanone, 1-(2,4,5-trihydroxyphenyl)MeSH
2,4,5-TrihydroxybutyrophenoneMeSH
(6R)-5,6,7,8-Tetrahydro-L-biopterinHMDB
(6R)-5,6,7,8-TetrahydrobiopterinHMDB
(6R)-TetrahydrobiopterinHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneHMDB
6R-Tetrahydro-L-biopterinHMDB
6beta-5,6,7,8-Tetrahydro-L-biopterinHMDB
6β-5,6,7,8-Tetrahydro-L-biopterinHMDB
L-erythro-TetrahydrobiopterinHMDB
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinoneHMDB
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP-1.7ALOGPS
logP-2.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.52ChemAxon
pKa (Strongest Basic)1.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9810000000-1bfd11724596b460cae9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-6945000000-07faa91218e86d3bfe0dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-0290000000-cd4c8c11b8279075b00aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0006-0390000000-35dddce9e2df2a9ac198View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0006-0590000000-cda875209a034e44cbe1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00kf-0980000000-53721c484501c528e7a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014l-0930000000-533fabd35a8c5ca7830eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-014i-0910000000-580c038db540047891c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-014i-0910000000-8d6b754dadadb6330906View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0006-0090000000-f21b677255493f1f2d1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-014i-0900000000-5c1b60d0d7ea4dd4dbffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-014i-1900000000-6f22457ab99b14bb653eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-014i-1900000000-cd0410f4da61716c7f9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-2900000000-d4f18a979b6d07e83a63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0002-0900000000-87174b78444828c3b52dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0a4i-0900000000-dc272a476d306f26c722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-014i-0900000000-ae19513d01a0046ed2e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-004i-0900000000-d4a52489d35bde573bd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0f79-0900000000-af02b0d9eb8f6577afb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-014i-0900000000-c2259602e8f1fd522fd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-c88ed5ea9e11715bc275View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-e6b01d1139ccb3c6338dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi3-0980000000-8963ef41f1138b05a813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1900000000-bcfa359703563c696c0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-4810efa20f31adea3824View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-1930000000-5b32feeb643e238bb159View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a7dbebeb1df4ea110948View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID59560
HMDB IDHMDB0059658
Pubchem Compound ID44257
Kegg IDC00272
ChemSpider ID40270
Wikipedia IDSapropterin
BioCyc IDNot Available