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2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
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ChemBase ID:
105333
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Molecular Formular:
C9H11N5O3
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Molecular Mass:
237.21534
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Monoisotopic Mass:
237.08618924
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SMILES and InChIs
SMILES:
C[C@H](O)C(=O)C1=Nc2c(NC1)[nH]c(N)nc2=O
Canonical SMILES:
C[C@@H](C(=O)C1=Nc2c(NC1)[nH]c(nc2=O)N)O
InChI:
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
InChIKey:
VPVOXUSPXFPWBN-VKHMYHEASA-N
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Cite this record
CBID:105333 http://www.chembase.cn/molecule-105333.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
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IUPAC Traditional name
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Synonyms
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Sepiapterin
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L-Sepiapterin
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S-(-)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone
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Sepiapterin
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L-SEPIAPTERIN DIHYDRATE
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S-(-)-2-氨基-7,8-二氢-6-(2-羟基-1-氧代丙基)-4(1H)-蝶啶酮
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墨蝶呤
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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CHEMBL
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Chemspider ID
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KEGG ID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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7.9298806
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H Acceptors
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8
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H Donor
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4
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LogD (pH = 5.5)
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-1.3707932
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LogD (pH = 7.4)
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-1.4704309
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Log P
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-1.3689492
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Molar Refractivity
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67.4968 cm3
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Polarizability
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21.422352 Å3
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Polar Surface Area
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129.17 Å2
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Rotatable Bonds
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2
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Lipinski's Rule of Five
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true
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PROPERTIES
PROPERTIES
Physical Property
Safety Information
Pharmacology Properties
Product Information
Bioassay(PubChem)
Solubility
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0.1 M NaOH: soluble9.8 mg/mL
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Show
data source
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DMSO: soluble27 mg/mL
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Show
data source
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Apperance
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yellow solid
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Show
data source
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Storage Condition
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-20°C, Desiccate, Store Under Nitrogen, Protect from light
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Show
data source
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MSDS Link
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German water hazard class
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3
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Show
data source
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Personal Protective Equipment
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Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
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Show
data source
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Storage Temperature
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-20°C
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Show
data source
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Gene Information
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human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
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Show
data source
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Purity
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≥99%
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Show
data source
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Certificate of Analysis
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abs.
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εmax/409 nm, 0.1 M HCl 6170
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Show
data source
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εmax1%/271 nm, 0.1 M HCl 7410
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Show
data source
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Empirical Formula (Hill Notation)
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C9H11N5O3
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Show
data source
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DETAILS
DETAILS
MP Biomedicals
Wikipedia
Sigma Aldrich
MP Biomedicals -
02195063
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Purity: >99% Dihydrate Important intermediate in the pterin salvage pathway, tetrahydropterin biosynthesis. |
MP Biomedicals -
02159813
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Sepiapterin is converted intracellularly into tetrahydrobiopterin, which causes stimulation of NO production. |
Sigma Aldrich -
S154
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Biochem/physiol Actions Cofactor of nitric oxide synthase; intracellularly converted to tetrahydro-biopterin leading to the stimulation of nitric oxide. Packaging 25 mg in poly bottle 5 mg in glass bottle |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Nichol, C., et al., Annu. Rev. Biochem. , 54 : 729, (1985).
- • Gross, S.S. and Levi, R.J., J. Biol. Chem. , 267 : 25722, (1992).
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PATENTS
PATENTS
PubChem Patent
Google Patent