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62996-74-1 molecular structure
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(2S,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-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),21,23,25-nonaen-16-one

ChemBase ID: 134161
Molecular Formular: C28H26N4O3
Molecular Mass: 466.53104
Monoisotopic Mass: 466.20049071
SMILES and InChIs

SMILES:
C[C@@]12[C@@H]([C@@H](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3C(=O)NC1)NC)OC
Canonical SMILES:
CN[C@@H]1C[C@@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
InChI:
InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20+,26-,28+/m1/s1
InChIKey:
HKSZLNNOFSGOKW-WIFUGMKFSA-N

Cite this record

CBID:134161 http://www.chembase.cn/molecule-134161.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-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),21,23,25-nonaen-16-one
(2S,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8(13),9,11,14(28),15(19),20(27),21,23,25-nonaen-16-one
IUPAC Traditional name
(2S,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-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),21,23,25-nonaen-16-one
(2S,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8(13),9,11,14(28),15(19),20(27),21,23,25-nonaen-16-one
Synonyms
Antibiotic AM-2282
Staurosporine from Streptomyces sp.
CAS Number
62996-74-1
MDL Number
MFCD00077402
Beilstein Number
1060573
PubChem SID
24899603
24899680
162228438
PubChem CID
9937179

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 9937179 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.562835  H Acceptors
H Donor LogD (pH = 5.5) 0.7899368 
LogD (pH = 7.4) 1.8470752  Log P 3.9696732 
Molar Refractivity 132.3721 cm3 Polarizability 55.985493 Å3
Polar Surface Area 69.45 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
H2O: insoluble expand Show data source
methanol: soluble expand Show data source
Apperance
film expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-46 expand Show data source
Safety Statements
53-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H340-H350 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥95.0% (HPLC) expand Show data source
Grade
for molecular biology expand Show data source
Quality Level
PREMIUM expand Show data source
Empirical Formula (Hill Notation)
C28H26N4O3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - S5921 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
Tested for inhibition of interleukin 2 production in Jurkat cells.
Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Partially reverses MDR, sensitizing cells with MDR phenotype to cytotoxic agents. Inhibits Pgp phosphorylation. However, functional significance of Pgp phosphorylation is ill defined.
Sigma Aldrich - S4400 external link
Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Partially reverses MDR, sensitizing cells with MDR phenotype to cytotoxic agents. Inhibits Pgp phosphorylation. However, functional significance of Pgp phosphorylation is ill defined.
Sigma Aldrich - 85658 external link
Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Sigma Aldrich - 85660 external link
Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Other Notes
A potent inhibitor of phospholipid / calcium dependent protein kinase1,2; Inhibits the respiratory burst and induces exocytosis in human neutrophils3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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