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17094-01-8 molecular structure
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2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one

ChemBase ID: 105333
Molecular Formular: C9H11N5O3
Molecular Mass: 237.21534
Monoisotopic Mass: 237.08618924
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

Cite this record

CBID:105333 http://www.chembase.cn/molecule-105333.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
IUPAC Traditional name
sepiapterin
Synonyms
Sepiapterin
L-Sepiapterin
S-(-)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone
Sepiapterin
L-SEPIAPTERIN DIHYDRATE
S-(-)-2-氨基-7,8-二氢-6-(2-羟基-1-氧代丙基)-4(1H)-蝶啶酮
墨蝶呤
CAS Number
17094-01-8
MDL Number
MFCD00210214
PubChem SID
162093831
24278058
PubChem CID
65253
CHEMBL
1255653
Chemspider ID
58746
KEGG ID
C00835
Wikipedia Title
Sepiapterin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.9298806  H Acceptors
H Donor LogD (pH = 5.5) -1.3707932 
LogD (pH = 7.4) -1.4704309  Log P -1.3689492 
Molar Refractivity 67.4968 cm3 Polarizability 21.422352 Å3
Polar Surface Area 129.17 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M NaOH: soluble9.8 mg/mL expand Show data source
DMSO: soluble27 mg/mL expand Show data source
Apperance
yellow solid expand Show data source
Storage Condition
-20°C, Desiccate, Store Under Nitrogen, Protect from light expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846) expand Show data source
Purity
≥99% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
abs.
εmax/409 nm, 0.1 M HCl 6170 expand Show data source
εmax1%/271 nm, 0.1 M HCl 7410 expand Show data source
Empirical Formula (Hill Notation)
C9H11N5O3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02195063 external link
Purity: >99%
Dihydrate
Important intermediate in the pterin salvage pathway, tetrahydropterin biosynthesis.
MP Biomedicals - 02159813 external link
Sepiapterin is converted intracellularly into tetrahydrobiopterin, which causes stimulation of NO production.
Sigma Aldrich - S154 external link
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 IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle 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

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INTERNET

INTERNET

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