6,7-dihydrobiopterin (PAMDB120052)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120052
Identification
Name: 6,7-dihydrobiopterin
Description:Not Available
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 6,7-dihydrobiopterin
  • 6,7-Dihydrobiopterin
  • 6,7-dihydrobiopterin
  • Dihydrobiopterin
  • q-dihydrobiopterin
  • Quinoid-dihydrobiopterin
  • quinoid-dihydrobiopterin
Chemical Formula: C9H13N5O3
Average Molecular Weight: 239.233
Monoisotopic Molecular Weight: 239.10184
InChI Key: ZHQJVZLJDXWFFX-BYAPIUGTSA-N
InChI: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
CAS number: 79647-29-3
IUPAC Name:2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydropteridin-4(6H)-one
Traditional IUPAC Name: (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-1H-pteridin-4-one
SMILES:CC(O)C(O)C2(N=C1(C(N=C(N)N=C1NC2)=O))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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 Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct Parent Biopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: 218 - 221 °C
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
Biological Properties
Cellular Locations: Not Available
Reactions:
TETRA-H-BIOPTERIN + L-Phenylalanine + Oxygen → 6,7-dihydrobiopterin + L-Tyrosine + Water
Pathways:
    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
    References
    References:
    • 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 ]
    • 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 ]
    • 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 ]
    • 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 ]
    • 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 ]
    • 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 ]
    • 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 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC20680
    HMDBHMDB02215
    LIGAND-CPDC00268
    CHEBI20680
    PUBCHEM1879