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154589-96-5 molecular structure
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N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide

ChemBase ID: 154314
Molecular Formular: C35H28N4O5
Molecular Mass: 584.62062
Monoisotopic Mass: 584.20597002
SMILES and InChIs

SMILES:
C[C@@]12[C@@H]([C@@H](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C)C(=O)c1ccccc1)OC
Canonical SMILES:
CO[C@@H]1[C@@H](C[C@@H]2O[C@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C(=O)c1ccccc1)C
InChI:
InChI=1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24+,31-,35+/m1/s1
InChIKey:
MQCCJEYZKWZQHU-JTPSWESPSA-N

Cite this record

CBID:154314 http://www.chembase.cn/molecule-154314.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
IUPAC Traditional name
N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
Synonyms
Stauprimide
CAS Number
154589-96-5
PubChem SID
162248453
PubChem CID
71311840

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
S2951 external link Add to cart Please log in.
Data Source Data ID
PubChem 71311840 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.031408  H Acceptors
H Donor LogD (pH = 5.5) 5.3271093 
LogD (pH = 7.4) 5.238331  Log P 5.3284235 
Molar Refractivity 163.3356 cm3 Polarizability 66.67411 Å3
Polar Surface Area 94.8 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: >20 mg/mL expand Show data source
Apperance
white to off-white powder expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C35H28N4O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - S2951 external link
Biochem/physiol Actions
Stauprimide is an enhancer stem cell differentiation into endoderm. In vitro differentiation of embryonic stem cells is of great interest to regenerative medicine, and current protocols are labor-intensive and expensive. Small molecules that induce or enhance differentiation are highly desired. High-content screening identified compounds that enhance endodermal differentiation in the presence of low levels of Activin A. Stauprimide increased definitive endodermal markers but not markers for visceral/parietal endoderm or mesoderm. Stauprimide-differentiated cells could be further differentiated into hepatocytes. Stauprimide treatment during differentiation decreased the concentration of Activin A required for definitive endoderm formation, and it eliminated the need for serum. The mechanism of action of stauprimide is to sensitize cells for differentiation. Stauprimide enabled differentiation into other cell lineages under varying differentiation conditions, including neurons, hematopoietic mesoderm, beating cardiac myocytes, and skeletal muscle. The cellular target of stauprimide was determined to be inhibition of NME2 transcription factor translocation to the nucleus, leading to down-regulation of c-Myc expression.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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