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Record Information
Version3.6
Creation Date2006-05-22 14:17:42 UTC
Update Date2016-02-11 01:05:27 UTC
HMDB IDHMDB02215
Secondary Accession NumbersNone
Metabolite Identification
Common Name4a-Carbinolamine tetrahydrobiopterin
DescriptionCarbinolamine 4a-hydroxytetrahydrobiopterin is formed as a consequence of the hydroxylation of phenylalanine to tyrosine. During the physiological reaction tetrahydrobiopterin (the naturally occurring cofactor for phenylalanine hydroxylase), and the two substrates phenylalanine and molecular oxygen combine with phenylalanine hydroxylase to form a quarternary complex. An enzyme, 4a-carbinolamine dehydratase, catalyzes the reaction. (PMID: 2722790 ).
Structure
Thumb
Synonyms
ValueSource
6,7-DihydrobiopterinKegg
Quinoid-dihydrobiopterinKegg
(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
Chemical FormulaC9H13N5O3
Average Molecular Weight239.2312
Monoisotopic Molecular Weight239.101839307
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
CAS Registry Number79647-29-3
SMILES
[H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O
InChI Identifier
InChI=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 KeyInChIKey=ZHQJVZLJDXWFFX-RPDRRWSUSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Pyrimidone
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.45 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.03 m3·mol-1ChemAxon
Polarizability22.77 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-b31c78b3d2240e4d4d45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h93-0970000000-508a25d7544d515036cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ka-1900000000-1e9eed496ea8538f6b17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0390000000-2d9ea64f3bb5145f0a23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0930000000-8ebd581c355cfdf37d59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9600000000-17f4849b21b55c8bd6b3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Epidermis
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.18 +/- 0.04 uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022911
KNApSAcK IDNot Available
Chemspider ID117564
KEGG Compound IDC00268
BioCyc IDCPD-16
BiGG IDNot Available
Wikipedia Link1,3,5-Trihydroxybenzene
NuGOwiki LinkHMDB02215
Metagene LinkHMDB02215
METLIN ID6552
PubChem Compound133246
PDB IDH2B
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [8128228 ]
  2. 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. [12860038 ]
  3. 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. [14565560 ]
  4. 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. [16454126 ]
  5. 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. [2225712 ]
  6. 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. [6617639 ]
  7. 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. [2722790 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular weight:
55611.26
Reactions
L-erythro-tetrahydrobiopterin + L-Tyrosine + Oxygen → L-Dopa + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
Reactions
L-erythro-tetrahydrobiopterin + L-Phenylalanine + Oxygen → 4a-Carbinolamine tetrahydrobiopterin + L-Tyrosine + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
Reactions
L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
Reactions
L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in oxidoreductase activity
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:
P09417
Molecular weight:
25789.295
Reactions
4a-Carbinolamine tetrahydrobiopterin + NADH + Hydrogen Ion → L-erythro-tetrahydrobiopterin + NADdetails
4a-Carbinolamine tetrahydrobiopterin + NADPH + Hydrogen Ion → L-erythro-tetrahydrobiopterin + NADPdetails
General function:
Involved in 4-alpha-hydroxytetrahydrobiopterin dehydratase activity
Specific function:
Involved in tetrahydrobiopterin biosynthesis. Seems to both prevent the formation of 7-pterins and accelerate the formation of quinonoid-BH2. Coactivator for HNF1A-dependent transcription. Regulates the dimerization of homeodomain protein HNF1A and enhances its transcriptional activity.
Gene Name:
PCBD1
Uniprot ID:
P61457
Molecular weight:
11999.515
Reactions
4a-Hydroxytetrahydrobiopterin → 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in 4-alpha-hydroxytetrahydrobiopterin dehydratase activity
Specific function:
Involved in tetrahydrobiopterin biosynthesis. Seems to both prevent the formation of 7-pterins and accelerate the formation of quinonoid-BH2 (By similarity). Regulates the dimerization of homeodomain protein HNF-1-alpha and enhances its transcriptional activity.
Gene Name:
PCBD2
Uniprot ID:
Q9H0N5
Molecular weight:
14365.325
Reactions
4a-Hydroxytetrahydrobiopterin → 4a-Carbinolamine tetrahydrobiopterin + Waterdetails