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154-42-7 molecular structure
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2-amino-6,7-dihydro-1H-purine-6-thione

ChemBase ID: 102918
Molecular Formular: C5H5N5S
Molecular Mass: 167.1917
Monoisotopic Mass: 167.02656619
SMILES and InChIs

SMILES:
Nc1nc2c([nH]cn2)c(=S)[nH]1
Canonical SMILES:
Nc1nc2nc[nH]c2c(=S)[nH]1
InChI:
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChIKey:
WYWHKKSPHMUBEB-UHFFFAOYSA-N

Cite this record

CBID:102918 http://www.chembase.cn/molecule-102918.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-6,7-dihydro-1H-purine-6-thione
IUPAC Traditional name
2-aminopurine-6(1h)-thione
Synonyms
6-Thioguanine
2-Amino-6-purinethiol
2-AMINO-6-MERCAPTOPURINE
6-Thioguanine
2-Amino-6-mercaptopurine
2-amino-1,7-dihydro-6H-purine-6-thione
2-氨基-6-巯嘌呤
2-氨基-6巯基嘌呤
6-硫鸟嘌呤
CAS Number
154-42-7
EC Number
205-827-2
MDL Number
MFCD00233553
MFCD00005568
Beilstein Number
157765
PubChem SID
162090773
24890892
24890748
PubChem CID
2723601

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.962727  H Acceptors
H Donor LogD (pH = 5.5) -0.22414501 
LogD (pH = 7.4) -0.21823545  Log P -0.21708015 
Molar Refractivity 47.3254 cm3 Polarizability 16.347652 Å3
Polar Surface Area 79.09 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
lyophilized powder expand Show data source
Melting Point
≥300 °C(lit.) expand Show data source
359 - 360°C expand Show data source
Hydrophobicity(logP)
-1.882 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
UP0740000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
R:22-36/37/38-47 expand Show data source
Safety Statements
28-36/37/39-45 expand Show data source
S:20-26-37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Purity
~98% expand Show data source
≥96% (HPLC) expand Show data source
≥98% expand Show data source
95% expand Show data source
Concentration
50 × expand Show data source
Grade
Hybri-Max™ expand Show data source
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for hybridoma expand Show data source
Impurities
≤3% guanine expand Show data source
endotoxin, tested expand Show data source
Sterility
γ-irradiated expand Show data source
Product Line
BioXtra expand Show data source
Empirical Formula (Hill Notation)
C5H5N5S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02105542 external link
Crystalline
Purity: Approx. 98%
Antineoplastic
Sigma Aldrich - A4660 external link
Application
Used in hybridoma formation applications as a selection agent.
Reconstitution
Reconstitute contents of vial with 10 ml sterile cell culture medium. Stock solution is sufficient to prepare 500 ml medium. Final working concentration: 30 μM 2-amino-6-mercaptopurine.
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1
Legal Information
Hybri-Max is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - A4882 external link
Biochem/physiol Actions
Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase, which catalzyes a critical step in the generation of purine nucleotides.
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1
包装
1, 5 g in glass bottle
100, 250, 500 mg in glass bottle
Sigma Aldrich - A76907 external link
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1
Sigma Aldrich - 88800 external link
Other Notes
Antineoplastic agent2; substrate for HGPRTase, converted to 6-thio-GMP, which then inhibits vital metabolic sequences in myelocytic and acute lymphocytic leukemia.1
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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