Basic Description

Synonyms	SCHEMBL218999 \| HY-19527 \| IST5-002 \| 5'-Adenylic acid, N-(phenylmethyl)- \| BDBM50056973 \| N(6)-Benzyladenosine-5'-monophosphate \| ((2R,3S,4R,5R)-5-(6-(Benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate \| DWVANBHPEPS
Specifications & Purity	≥99%
Biochemical and Physiological Mechanisms	IST5-002, a potent Stat5a/b inhibitor, selectively inhibits transcriptional activity of Stat5a/b ( IC 50 s: 1.5 μM for Stat5a, 3.5 μM for Stat5b). IST5-002 inducs cell apoptotic and death of prostate cancer cells and chronic myeloid leukemia (CML) cells.
Storage Temp	Store at -20°C
Shipped In	Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available.
Product Description	IST5-002, a potent Stat5a/b inhibitor, selectively inhibits transcriptional activity of Stat5a/b ( IC 50 s: 1.5 μM for Stat5a, 3.5 μM for Stat5b). IST5-002 inducs cell apoptotic and death of prostate cancer cells and chronic myeloid leukemia (CML) cells. IST5-002 can be used in the research of prostate cancer and chronic myeloid leukemia (CML) In Vitro IST5-002 (1.5-25 μM, 2 h) inhibits transcriptional activity of Stat5a and Stat5b in a dose-dependent manner. IST5-002 (0-40 μM, 3 h) inhibits Bcr-Abl-induced Stat5a/b phosphorylation in K562 cells. IST5-002 (5-100 μM, 2 h) inhibits Stat5a/b phosphorylation in T47D cells, and inhibits dimerization in PC-3 cells. IST5-002 (5-100 μM, 2 h) suppresses Stat5 nuclear translocation in PC-3 cells, and inhibits DNA binding of Stat5 target genes and COS-7 cells. IST5-002 (2-50 μM, 48 h) reduces expression of Stat5a/b target genes (Bcl-xL and cyclin D1) in CWR22Rv1 and LNCaP cells. IST5-002 (3.1-50 μM, 72 h) inhibits cell growth through induction of apoptosis in human prostate cancer cells. IST5-002 (25-100 μM, 7 days) induces epithelial cell death in patient-derived prostate cancers ex vivo in organ explant cultures. IST5-002 (5 μM, 24-72h) inhibits Stat5a/b phosphorylation and induces apoptosis of Imatinib -sensitive and -resistant CML cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: CWR22Rv1, LNCaP, and DU145 cells Concentration: 3.1, 6.3, 12.5, 25, 50 μM Incubation Time: 72 h Result: Decreased viable cells by 50% to 80% at 12.5 μM. Cell Cycle AnalysisCell Line: LNCaP and CWR22Rv1 cells Concentration: 6, 12, 25 μM Incubation Time: 72 h Result: Increased the fraction of dead cells (sub-G1) and decreased the fraction of living cells (G2–M). Western Blot AnalysisCell Line: Bcr-Abl–positive K562 cells Concentration: 0, 1, 5, 10, 20, 40 μM Incubation Time: 3 h Result: Inhibited Bcr-Abl-induced Stat5a/b phosphorylation at 5 μM, without affecting Bcr-Abl tyrosine phosphorylation levels. ImmunofluorescenceCell Line: PC-3 cells Concentration: 5, 10, 15. 20, 40 μM Incubation Time: 2 h Result: Inhibited Prl (Prolactin)-induced nuclear translocation of Stat5. In Vivo RORγt inverse agonist 29 (intraperitoneal injection, 25-100 mg/kg, daily for 10 days) inhibits tumor growth in prostate cancer xenograft model . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Prostate cancer (CWR22Rv1) xenograft model Dosage: 25, 50, and 100 mg/kg Administration: Intraperitoneal injection, daily for 10 days Result: Induced massive loss of viable tumor cells and dead rounded cells accumulation. Induced cell death through apoptosis (shown by fragmented DNA in tumor sections). Decreased nuclear Stat5a/b content by 60%, 78%, and 90% at 25, 50, and 100 mg/kg, respectively. Form:Solid IC50& Target:STAT5a 1.5 μM (IC 50 ) STAT5b 3.5 μM (IC 50 )

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Nucleosides, nucleotides, and analogues
  - Class Purine nucleotides
    - Subclass Purine ribonucleotides

Kingdom	Organic compounds
Superclass	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Subclass	Purine ribonucleotides
Intermediate Tree Nodes	Not available
Direct Parent	Purine ribonucleoside monophosphates
Alternative Parents	Pentose phosphates 6-alkylaminopurines Glycosylamines Monosaccharide phosphates Benzylamines Aminopyrimidines and derivatives Secondary alkylarylamines Monoalkyl phosphates Imidolactams N-substituted imidazoles Heteroaromatic compounds Tetrahydrofurans 1,2-diols Secondary alcohols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Purine ribonucleoside monophosphate - Pentose phosphate - Pentose-5-phosphate - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Monosaccharide phosphate - Pentose monosaccharide - Imidazopyrimidine - Purine - Benzylamine - Aminopyrimidine - Monoalkyl phosphate - Secondary aliphatic/aromatic amine - Monocyclic benzene moiety - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Imidolactam - Phosphoric acid ester - Benzenoid - Alkyl phosphate - Pyrimidine - Tetrahydrofuran - Azole - Heteroaromatic compound - Imidazole - Secondary alcohol - 1,2-diol - Azacycle - Secondary amine - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Alcohol - Organopnictogen compound - Amine - Organonitrogen compound - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

LPAR1 Tchem Lysophosphatidic acid receptor Edg-2 (779 Activities)

Discover Target: LPAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR2 Tchem Lysophosphatidic acid receptor Edg-4 (418 Activities)

Discover Target: LPAR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR3 Tchem Lysophosphatidic acid receptor Edg-7 (471 Activities)

Discover Target: LPAR3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR4 Tchem Lysophosphatidic acid receptor 4 (71 Activities)

Discover Target: LPAR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR5 Tchem Lysophosphatidic acid receptor 5 (213 Activities)

Discover Target: LPAR5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

IUPAC Name	[(2R,3S,4R,5R)-5-[6-(benzylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
INCHI	InChI=1S/C17H20N5O7P/c23-13-11(7-28-30(25,26)27)29-17(14(13)24)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-24H,6-7H2,(H,18,19,20)(H2,25,26,27)/t11-,13-,14-,17-/m1/s1
InChIKey	DWVANBHPEPSMOV-LSCFUAHRSA-N
Smiles	C1=CC=C(C=C1)CNC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)COP(=O)(O)O)O)O
Isomeric SMILES	C1=CC=C(C=C1)CNC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)COP(=O)(O)O)O)O
Alternate CAS	13484-66-7
PubChem CID	59310
MeSH Entry Terms	benzyl-adenosine monophosphate;benzyl-AMP
Molecular Weight	437.34

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

Chemical and Physical Properties

Solubility	DMSO : 125 mg/mL (285.82 mM; Need ultrasonic) H2O : 125 mg/mL (285.82 mM; Need ultrasonic)
Molecular Weight	437.300 g/mol
XLogP3	-1.400
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Exact Mass	437.11 Da
Monoisotopic Mass	437.11 Da
Topological Polar Surface Area	172.000 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	621.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

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SKU	Size	Availability	Price
I649511-1mg	1mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$300.90
I649511-5mg	5mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$610.90
I649511-10mg	10mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$980.90

IST5-002 - 99%, high purity , CAS No.13484-66-7