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22150-76-1 molecular structure
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2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one

ChemBase ID: 126161
Molecular Formular: C9H11N5O3
Molecular Mass: 237.21534
Monoisotopic Mass: 237.08618924
SMILES and InChIs

SMILES:
O=c1nc([nH]c2ncc(nc12)[C@@H](O)[C@@H](O)C)N
Canonical SMILES:
C[C@@H]([C@@H](c1cnc2c(n1)c(=O)nc([nH]2)N)O)O
InChI:
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
InChIKey:
LHQIJBMDNUYRAM-DZSWIPIPSA-N

Cite this record

CBID:126161 http://www.chembase.cn/molecule-126161.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
IUPAC Traditional name
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
Synonyms
(1’R,2’S)-Biopterin
2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine
L-erythro-6-(1,2-Dihydroxypropyl)pterin
6-Biopterin
Biopterin
CAS Number
22150-76-1
EC Number
244-807-8
MDL Number
MFCD00036787
Beilstein Number
87860
PubChem SID
162220502
24891654
PubChem CID
445040
Chemspider ID
392795
KEGG ID
C06313
MeSH Name
Biopterin
Wikipedia Title
Biopterin

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.598084  H Acceptors
H Donor LogD (pH = 5.5) -1.1910951 
LogD (pH = 7.4) -1.3875011  Log P -1.1878132 
Molar Refractivity 58.1331 cm3 Polarizability 21.483948 Å3
Polar Surface Area 133.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Optical Rotation
[α]20/D -65±8°, c = 0.2% in 0.1 M HCl expand Show data source
RTECS
UO3506000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97% expand Show data source
≥98.0% (sum of enantiomers, HPLC) expand Show data source
Empirical Formula (Hill Notation)
C9H11N5O3 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B2517 external link
Application
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.
Sigma Aldrich - 14390 external link
Other Notes
Review: Chemical mechanisms in the action of pteridine coenzymes1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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