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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-07-01 14:27:31 UTC
NP-MRD IDNP0000204
Secondary Accession NumbersNone
Natural Product Identification
Common NameSepiapterin
DescriptionSepiapterin, also known as 2-amino-6-lactoyl-7,8-dihydropteridin-4(3H)-one, belongs to the class of organic compounds 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. Sepiapterin is also classified as a member of the pteridine class of organic chemicals. It is a yellow fluorescing pigment. Sepiapterin is an intermediate in the salvage pathway of tetrahydrobiopterin (BH(4)). More specifically, sepiapterin can be metabolized into tetrahydrobiopterin via the BH(4) salvage pathway. Tetrahydrobiopterin is an essential cofactor in humans for breakdown of phenylalanine and a catalyst of the metabolism of phenylalanine, tyrosine, and tryptophan to the neurotransmitters dopamine and serotonin. A deficiency of tetrahydrobiopterin can cause toxic buildup of phenylalanine (phenylketonuria) as well as deficiencies of dopamine, norepinephrine, and epinephrine, leading to dystonia and other neurological illnesses. Sepiapterin accumulates in the brain of patients with sepiapterin reductase (SR) deficiency, an inborn error of metabolism. Sepiapterin reductase deficiency is a condition characterized by movement problems, most often a pattern of involuntary, sustained muscle contractions known as dystonia. Other movement problems can include muscle stiffness (spasticity), tremors, problems with coordination and balance (ataxia), and involuntary jerking movements (chorea). People with sepiapterin reductase deficiency can experience episodes called oculogyric crises. These episodes involve abnormal rotation of the eyeballs; extreme irritability and agitation; and pain, muscle spasms, and uncontrolled movements, especially of the head and neck. Movement abnormalities are often worse late in the day. Most affected individuals have delayed development of motor skills such as sitting and crawling, and they typically are not able to walk unassisted. The problems with movement tend to worsen over time. Within humans, sepiapterin participates in a number of enzymatic reactions. In particular, sepiapterin can be converted into 7,8-dihydroneopterin; which is mediated by the enzyme sepiapterin reductase. In addition, sepiapterin can be converted into 7,8-dihydroneopterin through its interaction with the enzyme carbonyl reductase [NADPH] 1.
Structure
Thumb
Synonyms
ValueSource
(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-CHMDB
2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)- pteridinoneHMDB
Sepia-pterinHMDB
2-Amino-7,8-dihydro-6-((2S)-2-hydroxy-1-oxopropyl)-4(3H)-pteridinone acidHMDB
Chemical FormulaC9H11N5O3
Average Mass237.2153 Da
Monoisotopic Mass237.08619 Da
IUPAC Name2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
Traditional 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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-09-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)V.dorna832021-09-07View Spectrum
Species
Species of Origin
  • Animalia
  • Chemical Taxonomy
    Description Belongs to the class of organic compounds 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.
    KingdomOrganic compounds
    Super ClassOrganoheterocyclic compounds
    ClassPteridines and derivatives
    Sub ClassPterins and derivatives
    Direct ParentPterins and derivatives
    Alternative Parents
    Substituents
    • Pterin
    • Aminopyrimidine
    • Pyrimidone
    • Secondary aliphatic/aromatic amine
    • Acyloin
    • Pyrimidine
    • Alpha-hydroxy ketone
    • Heteroaromatic compound
    • Vinylogous amide
    • Secondary alcohol
    • Ketimine
    • Ketone
    • Propargyl-type 1,3-dipolar organic compound
    • Secondary amine
    • Azacycle
    • Organic 1,3-dipolar compound
    • Alcohol
    • Primary amine
    • Organooxygen compound
    • Organonitrogen compound
    • Organopnictogen compound
    • Organic oxide
    • Imine
    • Carbonyl group
    • Organic oxygen compound
    • Amine
    • Hydrocarbon derivative
    • Organic nitrogen compound
    • Aromatic heteropolycyclic compound
    Molecular FrameworkAromatic heteropolycyclic compounds
    External DescriptorsNot Available
    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)9.18ChemAxon
    pKa (Strongest Basic)-1.3ChemAxon
    Physiological Charge0ChemAxon
    Hydrogen Acceptor Count8ChemAxon
    Hydrogen Donor Count4ChemAxon
    Polar Surface Area129.17 ŲChemAxon
    Rotatable Bond Count2ChemAxon
    Refractivity67.5 m³·mol⁻¹ChemAxon
    Polarizability22.44 ųChemAxon
    Number of Rings2ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000238
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021914
    KNApSAcK IDNot Available
    Chemspider ID58746
    KEGG Compound IDC00835
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkSepiapterin
    METLIN ID5244
    PubChem Compound65253
    PDB IDNot Available
    ChEBI ID804632
    Good Scents IDNot Available
    References
    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 ]
    2. Ranjpour M, Wajid S, Jain SK: Elevated expression of sepiapterin reductase, regulator of G protein signaling 1, hypothetical protein CXorf58 homolog, and zinc finger and BTB domain-containing protein 21 isoform X2 is associated with progression of hepatocellular carcinoma. Protoplasma. 2021 Mar 8. pii: 10.1007/s00709-021-01632-2. doi: 10.1007/s00709-021-01632-2. [PubMed:33683453 ]
    3. Lindsay A, Kemp B, Larson AA, Baumann CW, McCourt PM, Holm J, Karachunski P, Lowe DA, Ervasti JM: Tetrahydrobiopterin synthesis and metabolism is impaired in dystrophin-deficient mdx mice and humans. Acta Physiol (Oxf). 2021 Apr;231(4):e13627. doi: 10.1111/apha.13627. Epub 2021 Mar 8. [PubMed:33580591 ]
    4. Cherian A, Paramasivan NK, Divya KP: Dopa-responsive dystonia, DRD-plus and DRD look-alike: a pragmatic review. Acta Neurol Belg. 2021 Jun;121(3):613-623. doi: 10.1007/s13760-020-01574-1. Epub 2021 Jan 16. [PubMed:33453040 ]
    5. Zhang X, Chen Y, Wang K, Tang J, Chen Y, Jin G, Liu X: The knockdown of the sepiapterin reductase gene suppresses the proliferation of breast cancer by inducing ROS-mediated apoptosis. Int J Clin Exp Pathol. 2020 Sep 1;13(9):2228-2239. eCollection 2020. [PubMed:33042327 ]