ContaminantDB: Sapropterin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:22:08 UTC

Update Date

2016-11-09 01:21:13 UTC

Accession Number

CHEM034958

Identification

Common Name

Sapropterin

Class

Small Molecule

Description

A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

241.247 g/mol

Monoisotopic Mass

241.117 g/mol

CAS Registry Number

62989-33-7

IUPAC Name

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

Traditional Name

tetrahydrobiopterin

SMILES

C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2

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-BYAPIUGTSA-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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9810000000-1bfd11724596b460cae9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-014i-6945000000-07faa91218e86d3bfe0d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0006-0290000000-cd4c8c11b8279075b00a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0006-0390000000-35dddce9e2df2a9ac198	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0006-0590000000-cda875209a034e44cbe1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00kf-0980000000-53721c484501c528e7a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-014l-0930000000-533fabd35a8c5ca7830e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-014i-0910000000-580c038db540047891c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-014i-0910000000-8d6b754dadadb6330906	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0006-0090000000-f21b677255493f1f2d1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-014i-0900000000-5c1b60d0d7ea4dd4dbff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-014i-1900000000-6f22457ab99b14bb653e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014i-1900000000-cd0410f4da61716c7f9e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014i-2900000000-d4f18a979b6d07e83a63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0002-0900000000-87174b78444828c3b52d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0a4i-0900000000-dc272a476d306f26c722	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-ae19513d01a0046ed2e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-004i-0900000000-d4a52489d35bde573bd0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0f79-0900000000-af02b0d9eb8f6577afb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-c2259602e8f1fd522fd0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0006-0090000000-c88ed5ea9e11715bc275	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-e6b01d1139ccb3c6338d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gi3-0980000000-8963ef41f1138b05a813	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-1900000000-bcfa359703563c696c0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-4810efa20f31adea3824	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006y-1930000000-5b32feeb643e238bb159	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-a7dbebeb1df4ea110948	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum