Human Metabolome Database Version 3.5

Showing metabocard for Sepiapterin (HMDB00238)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:08 -0700
HMDB ID HMDB00238
Secondary Accession Numbers None
Metabolite Identification
Common Name Sepiapterin
Description Sepiapterin 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H11N5O3
Average Molecular Weight 237.2153
Monoisotopic Molecular Weight 237.086189243
IUPAC Name 2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC 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
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Pteridines and Derivatives
Substituents
  • Acyloin
  • Alpha Ketoaldehyde
  • Aminopyrimidine
  • Beta Aminoketone
  • Imine
  • Ketone
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct Parent Pterins and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.18 g/L ALOGPS
LogP -1.09 ALOGPS
LogP -1.4 ChemAxon
LogS -2.30 ALOGPS
pKa (strongest acidic) 7.93 ChemAxon
pKa (strongest basic) 3.16 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 129.17 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 67.5 ChemAxon
Polarizability 22.44 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pterine Biosynthesis SMP00005 map00790 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0005 (0.0-0.001) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
<0.0005 uM Children (1-13 year old) Male Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0083 (0.0056-0.011) uM Adult (>18 years old) Both Sepiapterin Reductase Deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.01375 (0.0075-0.02) uM Children (1-13 year old) Male sepiapterin 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 Link_out
      Associated OMIM IDs
      • 182125 Link_out (Sepiapterin reductase deficiency)
      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 Link_out
      KEGG Compound ID C00835 Link_out
      BioCyc ID CPD-374 Link_out
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00238 Link_out
      Metagene Link HMDB00238 Link_out
      METLIN ID 5244 Link_out
      PubChem Compound 65253 Link_out
      PDB ID Not Available
      ChEBI ID 804632 Link_out
      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 Link_out

      Enzymes
      Name: Sepiapterin reductase
      Reactions:
      Dihydrobiopterin + NADP unknown Sepiapterin + NADPH details
      Gene Name: SPR
      Uniprot ID: P35270 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 14-3-3 protein zeta/delta
      Reactions: Not Available
      Gene Name: YWHAZ
      Uniprot ID: P63104 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 14-3-3 protein beta/alpha
      Reactions: Not Available
      Gene Name: YWHAB
      Uniprot ID: P31946 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 14-3-3 protein gamma
      Reactions: Not Available
      Gene Name: YWHAG
      Uniprot ID: P61981 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA