4a-Carbinolamine tetrahydrobiopterin (CHEM035374)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:42:40 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035374
Identification
Common Name4a-Carbinolamine tetrahydrobiopterin
ClassSmall Molecule
DescriptionA 6,7-dihydrobiopterin that has R configuration at position 6 and in which the 1,2-dihydroxypropyl substituent has 1R,2S configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-6H-pteridin-4-oneChEBI
(6R)-6-[(1R,2S)-1,2-Dihydroxypropyl]-7,8-dihydro-6H-pterinChEBI
6,7-DihydrobiopterinChEBI
Q-H2BPTChEBI
Quinoid-dihydrobiopterinChEBI
Quinonoid 6,7-dihydrobiopterinChEBI
6-[(1R,2S)-1,2-Dihydroxypropyl]-6,7-dihydropterinKegg
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterinKEGG
1,3,5-BenzenetriolHMDB
1,3,5-TrihydroxybenzeneHMDB
1,3,5-Trihydroxybenzene anhydrateHMDB
1,3,5-Trihydroxybenzene anhydrousHMDB
1,3,5-Trihydroxybenzene dihydrateHMDB
1.3.5-TrihydroxybenzeneHMDB
4a-Hydroxy-BH4HMDB
PhloroglucinHMDB
PhloroglucinolHMDB
Phloroglucinol 2-hydrateHMDB
Phloroglucinol anhydrousHMDB
Phloroglucinol dihydrateHMDB
4a-Carbinolamine tetrahydrobiopterinChEBI
Chemical FormulaC9H13N5O3
Average Molecular Mass239.231 g/mol
Monoisotopic Mass239.102 g/mol
CAS Registry Number79647-29-3
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,6,7-tetrahydropteridin-4-one
Traditional Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-1H-pteridin-4-one
SMILES[H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O
InChI IdentifierInChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1
InChI KeyZHQJVZLJDXWFFX-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Imidolactam
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.45 g/LALOGPS
logP-1.4ALOGPS
logP-2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.69ChemAxon
pKa (Strongest Basic)1.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.66 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability22.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006y-9720000000-50fd5953817583278634Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-8195000000-9404a6359e671c74945fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-b31c78b3d2240e4d4d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h93-0970000000-508a25d7544d515036cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ka-1900000000-1e9eed496ea8538f6b17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0390000000-2d9ea64f3bb5145f0a23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0930000000-8ebd581c355cfdf37d59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9600000000-17f4849b21b55c8bd6b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4a6c2eb22faca2bd9c6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0290000000-bd0c7392c3c2b36c22d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-3900000000-5b4e107d96010101e0f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0920000000-a8316dedaf2ff7f68dc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-0910000000-d37051ed31fd26c17d8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxu-8900000000-28d0495ab110064f993bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02562
HMDB IDHMDB0002215
FooDB IDFDB022911
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6552
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID117564
ChEBI ID43120
PubChem Compound ID133246
Kegg Compound IDC00268
YMDB IDNot Available
ECMDB IDECMDB24076
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1380405
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19235519
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2722790
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6617639
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6849887
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8128228
7. Kim H, Roh H, Lee HJ, Chung SY, Choi SO, Lee KR, Han SB: Determination of phloroglucinol in human plasma by high-performance liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):307-12.
8. Ismaili L, Refouvelet B, Xicluna A, Robert JF, Guillaume YC: Phloroglucinol: novel synthesis and role of the magnesium cation on its binding with human serum albumin (HSA) using a biochromatographic approach based on Langmuir isotherms. J Pharm Biomed Anal. 2003 Jul 14;32(3):549-53.
9. Schallreuter KU, Wood JM, Pittelkow MR, Gutlich M, Lemke KR, Rodl W, Swanson NN, Hitzemann K, Ziegler I: Regulation of melanin biosynthesis in the human epidermis by tetrahydrobiopterin. Science. 1994 Mar 11;263(5152):1444-6.
10. Jafri W, Yakoob J, Hussain S, Jafri N, Islam M: Phloroglucinol in irritable bowel syndrome. J Pak Med Assoc. 2006 Jan;56(1):5-8.
11. Fiset C, LeBel M: Influence of the menstrual cycle on the absorption and elimination of D-xylose. Clin Pharmacol Ther. 1990 Nov;48(5):529-36.
12. Armarego WL, Randles D, Taguchi H: Peroxidase catalysed aerobic degradation of 5,6,7,8-tetrahydrobiopterin at physiological pH. Eur J Biochem. 1983 Oct 3;135(3):393-403.
13. Davis MD, Kaufman S: Evidence for the formation of the 4a-carbinolamine during the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase. J Biol Chem. 1989 May 25;264(15):8585-96.