GABAReceptorInhibitorgabareceptorinhibitor

Sepiapterin

By rofalproject
Common Name

Sepiapterin Description

Sepiapterin is an intermediate in the salvage pathway of tetrahydrobiopterin (BH(4)). It is a yellow fluorescing pigment. Sepiapterin accumliates in the brain of patients with sepiapterin reductase (SR) deficiency. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (S)-2-amino-7,8-dihydro-6-(2-Hydroxy-1-oxopropyl)-4(1H)-pteridinoneHMDB 1-(2-amino-7,8-dihydro-4-Hydroxy-6-pteridinyl)-2-hydroxy-1-propanoneHMDB 2-amino-6-(S)-Lactoyl-7,8-dihydro-4(3H)-pteridinoneHMDB 2-amino-7,8-dihydro-6-[(2S)-2-Hydroxy-1-oxopropyl]-4(1H)pteridinoneHMDB L-SepiapterinHMDB Lopac-S-154HMDB SepiapterineHMDB Sepiapterin-CMeSH 2-amino-6-(S)-Lactoyl-7,8-dihydro-4(3H)- pteridinoneMeSH Sepia-pterinMeSH

Chemical Formlia

C9H11N5O3 Average Molecliar Weight

237.2153 Monoisotopic Molecliar Weight

237.086189243 IUPAC Name

2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one Traditional Name

sepiapterin CAS Registry Number

17094-01-8 SMILES

C[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O

InChI Identifier

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1

InChI Key

VPVOXUSPXFPWBN-VKHMYHEASA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Pteridines and derivatives Direct Parent

Pterins and derivatives Alternative Parents

  • Secondary alkylarylamines
  • Pyrimidones
  • Aminopyrimidines and derivatives
  • Primary aromatic amines
  • Acyloins
  • Vinylogous amides
  • Heteroaromatic compounds
  • Alpha-hydroxy ketones
  • Secondary alcohols
  • Ketimines
  • Propargyl-type 1,3-dipolar organic compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Pterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Acyloin
  • Primary aromatic amine
  • Pyrimidine
  • Alpha-hydroxy ketone
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Ketimine
  • Ketone
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Imine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Component of Folate biosynthesis

    • Application

    Not Available Cellliar locations

  • Cytoplasm (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility1.18 mg/mLALOGPS logP-1.1ALOGPS logP-1.4ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)7.93ChemAxon pKa (Strongest Basic)3.16ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area129.17 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity67.5 m3·mol-1ChemAxon Polarizability22.44 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00ko-0950000000-2cf5caf622d639c89359View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0297-2900000000-f9fe1627a36e71b61db6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00di-3900000000-82cabe6461c502831c78View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm (predicted from logP)

    • Biofluid Locations

  • Cerebrospinal Fluid (CSF)

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Dopa-responsive dystoniaSMP00486Not Available Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencySMP00487Not Available Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)SMP00488Not Available Hyperphenylalaninemia due to dhpr-deficiencySMP00489Not Available Pterine BiosynthesisSMP00005map00790 Segawa syndromeSMP00490Not Available Sepiapterin reductase deficiencySMP00491Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Cerebrospinal Fluid (CSF)Detected and Quantified0.0005 (0.0-0.001) uMAdlit (>18 years old)BothNormal

  • 11855937

    • details Cerebrospinal Fluid (CSF)Detected and Quantified<0.0005 uMChildren (1-13 years old)MaleNormal

  • 18502672

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Cerebrospinal Fluid (CSF)Detected and Quantified0.0083 (0.0056-0.011) uMAdlit (>18 years old)BothSepiapterin Reductase Deficiency

  • 11855937

    • details Cerebrospinal Fluid (CSF)Detected and Quantified0.01375 (0.0075-0.02) uMChildren (1-13 years old)Malesepiapterin reductase deficiency

  • 18502672

    • details

    Associated Disorders and Diseases Disease References

    Sepiapterin reductase deficiency

    1. Zorzi G, Redweik U, Trippe H, Penzien JM, Thony B, Blau N: Detection of sepiapterin in CSF of patients with sepiapterin reductase deficiency. Mol Genet Metab. 2002 Feb;75(2):174-7. [PubMed:11855937 ]

    Associated OMIM IDs

  • 182125 (Sepiapterin reductase deficiency)

    • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021914 KNApSAcK ID

    Not Available Chemspider ID

    58746 KEGG Compound ID

    C00835 BioCyc ID

    CPD-374 BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00238 Metagene Link

    HMDB00238 METLIN ID

    5244 PubChem Compound

    65253 PDB ID

    Not Available ChEBI ID

    804632

    Product: KR-33494

    References Synthesis Reference Pfleiderer, Wolfgang. Synthesis and absolute configuration of sepiapterin. Chem. Biol. Pteridines, Proc. Int. Symp., 5th (1975), 941-9. Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Zorzi G, Redweik U, Trippe H, Penzien JM, Thony B, Blau N: Detection of sepiapterin in CSF of patients with sepiapterin reductase deficiency. Mol Genet Metab. 2002 Feb;75(2):174-7. [PubMed:11855937 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
    Gene Name:
    SPR
    Uniprot ID:
    P35270
    Molecular weight:
    28048.13
    Reactions
    Dihydrobiopterin + NADP → Sepiapterin + NADPH details
    General function:
    Involved in protein domain specific binding
    Specific function:
    Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner
    Gene Name:
    YWHAZ
    Uniprot ID:
    P63104
    Molecular weight:
    27744.8
    General function:
    Involved in protein domain specific binding
    Specific function:
    Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negative regulator of osteogenesis
    Gene Name:
    YWHAB
    Uniprot ID:
    P31946
    Molecular weight:
    28082.2
    General function:
    Involved in protein domain specific binding
    Specific function:
    Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner
    Gene Name:
    YWHAG
    Uniprot ID:
    P61981
    Molecular weight:
    28302.3

    PMID: 23048072

    By rofalproject

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