Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:08 UTC
HMDB IDHMDB00238
Secondary Accession NumbersNone
Metabolite Identification
Common NameSepiapterin
DescriptionSepiapterin is an intermediate in the salvage pathway of tetrahydrobiopterin (BH(4)). It is a yellow fluorescing pigment. Sepiapterin accumulates in the brain of patients with sepiapterin reductase (SR) deficiency.
Structure
Thumb
Synonyms
  1. (S)-2-amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-Pteridinone
  2. 1-(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-2-hydroxy-1-Propanone
  3. 2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)-pteridinone
  4. 2-Amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)Pteridinone
  5. L-Sepiapterin
  6. Lopac-S-154
  7. Sepiapterin
  8. Sepiapterine
Chemical FormulaC9H11N5O3
Average Molecular Weight237.2153
Monoisotopic Molecular Weight237.086189243
IUPAC Name2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC Namesepiapterin
CAS Registry Number17094-01-8
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 KeyVPVOXUSPXFPWBN-VKHMYHEASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPteridines and Derivatives
Sub ClassPterins and Derivatives
Other Descriptors
  • Pteridines and Derivatives
Substituents
  • Acyloin
  • Alpha Ketoaldehyde
  • Aminopyrimidine
  • Beta Aminoketone
  • Imine
  • Ketone
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPterins and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1.18 g/LALOGPS
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 area129.17ChemAxon
rotatable bond count2ChemAxon
refractivity67.5ChemAxon
polarizability22.44ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pterine BiosynthesisSMP00005map00790
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified0.0005 (0.0-0.001) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified<0.0005 uMChildren (1-13 year old)MaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified0.0083 (0.0056-0.011) uMAdult (>18 years old)BothSepiapterin Reductase Deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.01375 (0.0075-0.02) uMChildren (1-13 year old)Malesepiapterin reductase deficiency
Associated Disorders and Diseases
Disease References
Sepiapterin reductase deficiency
  • 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)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021914
KNApSAcK IDNot Available
Chemspider ID58746
KEGG Compound IDC00835
BioCyc IDCPD-374
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00238
Metagene LinkHMDB00238
METLIN ID5244
PubChem Compound65253
PDB IDNot Available
ChEBI ID804632
References
Synthesis ReferencePfleiderer, Wolfgang. Synthesis and absolute configuration of sepiapterin. Chem. Biol. Pteridines, Proc. Int. Symp., 5th (1975), 941-9.
Material Safety Data Sheet (MSDS)Not Available
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

Gene Name:
SPR
Uniprot ID:
P35270
Reactions
Dihydrobiopterin + NADP unknown Sepiapterin + NADPHdetails
Gene Name:
YWHAZ
Uniprot ID:
P63104
Gene Name:
YWHAB
Uniprot ID:
P31946
Gene Name:
YWHAG
Uniprot ID:
P61981