(3S,4S,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-8,10,12,14,19,21,23,25,27-nonaen-16-one
PubChem CID
6711321
Structure
Molecular Formula
Synonyms
- staurosporine
- (3S,4S,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-8,10,12,14,19,21,23,25,27-nonaen-16-one
- NSC618487
- NSC-618487
- NCI60_005573
Molecular Weight
466.5 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
- Create:2006-06-05
- Modify:2025-01-25
Description
An indolocarbazole that is a potent protein kinase C inhibitor which enhances cAMP-mediated responses in human neuroblastoma cells. (Biochem Biophys Res Commun 1995;214(3):1114-20)
Staurosporine is a cell permeable alkaloid isolated from Streptomyces staurosporeus exhibiting anti-cancer activity. Staurosporine is a potent, non-selective inhibitor of protein kinases, including protein kinase C. This agent induces apoptosis by an undetermined mechanism. (NCI)
An indolocarbazole that is a potent PROTEIN KINASE C inhibitor which enhances cAMP-mediated responses in human neuroblastoma cells. (Biochem Biophys Res Commun 1995;214(3):1114-20)
See also: Staurosporine (annotation moved to).
Chemical Structure Depiction
(3S,4S,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-8,10,12,14,19,21,23,25,27-nonaen-16-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)
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?/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
HKSZLNNOFSGOKW-VYEKLMEQSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
CC12[C@H]([C@H](C[C@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)NC)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C28H26N4O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)
62996-74-1
- 8,12-Epoxy-1H,8H-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-1-one, 2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-10-(methylamino)-, (8alpha,9beta,10beta,12alpha)-(+)-
- Staurosporine
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
466.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.2
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
466.20049070 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
466.20049070 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
69.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
35
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
901
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2010.01.29)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Staurosporine (annotation moved to)
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useStaurosporinehttps://www.drugbank.ca/drugs/DB02010
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- DTP/NCILICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- Metabolomics Workbench
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/aboutstaurosporinehttps://pharos.nih.gov/ligands/4UXS9UGRZQTR
- SpectraBaseSTAUROSPORINEhttps://spectrabase.com/spectrum/9ekOATRdogU
- WikipediaStaurosporinehttps://en.wikipedia.org/wiki/Staurosporine
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlStaurosporinehttps://www.ncbi.nlm.nih.gov/mesh/68019311Enzyme Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68004791
- PubChem
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