Molecule

Staurosporinone

AlkaPlorer ID: AK017017

Synonym: 6,7,12,13-Tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one, Staurosporine aglycone, K 252c

IUPAC Name: 3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one

Structure

SMILES: OC1=NCC2=C1C1=C(NC3=CC=CC=C31)C1=C2C2=CC=CC=C2N1

InChI: InChI=1S/C20H13N3O/c24-20-17-12(9-21-20)15-10-5-1-3-7-13(10)22-18(15)19-16(17)11-6-2-4-8-14(11)23-19/h1-8,22-23H,9H2,(H,21,24)

InChIKey: MEXUTNIFSHFQRG-UHFFFAOYSA-N

Reference

Production of the Staurosporine Aglycon K-252c with a Blocked Mutant of the Staurosporine Producer Strain Streptomyces longisporoflavus and by Biotransformation of Staurosporine with Streptomyces mediocidicus ATCC 13279.

PubChem CID: 3815

CAS: 85753-43-1

LOTUS: LTS0120415

NPASS: NPC195314

COCONUT: CNP0107474

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NPAtlas: NPA007264

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Nocardiopsis sp.	Nocardiopsis	Nocardiopsaceae	Streptosporangiales	Actinomycetes	Actinomycetota	None	Bacteria
None	Eudistoma	Polycitoridae	Aplousobranchia	Ascidiacea	Chordata	Metazoa	Eukaryota
Lycogala epidendrum	Lycogala	Enteridiidae	Liceales	Eumycetozoa	Evosea	None	Eukaryota
None	Eudistoma	Polycitoridae	Aplousobranchia	Ascidiacea	Chordata	Metazoa	Eukaryota
Lycogala epidendrum	Lycogala	Enteridiidae	Liceales	Eumycetozoa	Evosea	None	Eukaryota

Properties Information

Molecule Weight: 311.344

TPSA？: 64.17

MolLogP？: 4.773800000000002

Number of H-Donors: 3

Number of H-Acceptors: 1

RingCount: 6

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus cereus	Bacillus cereus	MIC	50.0	ug.mL-1	10.1021/jm9603779
Bos taurus	cAMP-dependent protein kinase alpha-catalytic subunit	IC50	10000.0	nM	10.1016/S0960-894X(01)80995-1
Bos taurus	cGMP-dependent protein kinase 1 alpha	IC50	650.0	nM	10.1016/S0960-894X(01)80995-1
Escherichia coli K-12	Beta-lactamase AmpC	Change in IC50	8.0	fold	10.1021/jm020427b
Escherichia coli K-12	Beta-lactamase AmpC	Change in IC50	50.0	fold	10.1021/jm020427b
Escherichia coli K-12	Beta-lactamase AmpC	IC50	8000.0	nM	10.1021/jm030266r
Escherichia coli K-12	Beta-lactamase AmpC	Inhibition	17.0	%	10.1021/jm030266r
Escherichia coli K-12	Beta-lactamase AmpC	Inhibition	80.0	%	10.1021/jm030266r
Gallus gallus	Myosin light chain kinase, smooth muscle	IC50	2800.0	nM	10.1016/S0960-894X(01)80995-1
Homo sapiens	78 kDa glucose-regulated protein	Potency	14125.4	nM	None
Homo sapiens	Beta-chymotrypsin	IC50	10000.0	nM	10.1021/jm020427b
Homo sapiens	CaM kinase II	IC50	184.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	cAMP-dependent protein kinase (PKA)	IC50	2000.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	cAMP-dependent protein kinase (PKA)	IC50	25700.0	nM	10.1016/S0960-894X(00)80167-5
Homo sapiens	cAMP-dependent protein kinase (PKA)	IC50	25700.0	nM	10.1021/jm020427b
Homo sapiens	Casein kinase II	Inhibition	67.0	%	10.1042/0264-6021:3510095
Homo sapiens	c-Jun N-terminal kinase 1	Inhibition	82.0	%	10.1042/0264-6021:3510095
Homo sapiens	Cyclin-dependent kinase 1/cyclin B	IC50	nan	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	Cyclin-dependent kinase 2/cyclin E	IC50	1000.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	Cyclin-dependent kinase 2/cyclin E	IC50	1000.0	nM	10.1016/s0960-894x(03)00792-3
Homo sapiens	Cyclin-dependent kinase 4/cyclin D1	IC50	830.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	Cyclin-dependent kinase 4/cyclin D1	IC50	830.0	nM	10.1016/s0960-894x(03)00792-3
Homo sapiens	DNA topoisomerase I	MIC	10.0	ug.mL-1	10.1021/jm9603779
Homo sapiens	DNA topoisomerase II beta	MIC	10.0	ug.mL-1	10.1021/jm9603779
Homo sapiens	Eyes absent homolog 2	Potency	1901.5	nM	None
Homo sapiens	Glycogen synthase kinase-3 beta	Inhibition	84.0	%	10.1042/0264-6021:3510095
Homo sapiens	HCT-116	IC50	1720.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	HCT-116	IC50	1720.0	nM	10.1016/s0960-894x(03)00792-3
Homo sapiens	HepG2	Potency	12589.3	nM	None
Homo sapiens	Jurkat	IC50	nan	None	10.1016/j.bmcl.2009.04.039
Homo sapiens	K562	IC50	7800.0	nM	10.1016/j.bmc.2016.05.032
Homo sapiens	MAP kinase-activated protein kinase 2	Inhibition	83.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase-activated protein kinase 5	Inhibition	50.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase ERK2	Inhibition	37.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase p38 alpha	Inhibition	100.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase p38 beta	Inhibition	88.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase p38 delta	Inhibition	93.0	%	10.1042/0264-6021:3510095
Homo sapiens	MAP kinase p38 gamma	Inhibition	64.0	%	10.1042/0264-6021:3510095
Homo sapiens	Mitogen-activated protein kinase kinase kinase 11	IC50	49.0	nM	10.1021/jm051074u
Homo sapiens	Mitogen-activated protein kinase kinase kinase 9	IC50	138.0	nM	10.1021/jm051074u
Homo sapiens	Mothers against decapentaplegic homolog 3	Potency	12589.3	nM	None
Homo sapiens	NCI-H460	IC50	3200.0	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	NCI-H460	IC50	3200.0	nM	10.1016/s0960-894x(03)00792-3
Homo sapiens	Nuclear factor erythroid 2-related factor 2	Potency	29092.9	nM	None
Homo sapiens	PANC-1	Selectivity Index	3.0	None	10.1021/jm801420y
Homo sapiens	Protein kinase C alpha	IC50	2450.0	nM	10.1021/jm9603779
Homo sapiens	Protein kinase C alpha	Inhibition	60.0	%	10.1042/0264-6021:3510095
Homo sapiens	Protein kinase C (PKC)	IC50	2450.0	nM	10.1016/S0960-894X(00)80167-5
Homo sapiens	Protein kinase C (PKC)	IC50	2450.0	nM	10.1021/acs.jmedchem.7b01231
Homo sapiens	Protein kinase C (PKC)	IC50	2450.0	nM	10.1021/jm020427b
Homo sapiens	Protein kinase C (PKC)	IC50	nan	nM	10.1016/s0960-894x(03)00791-1
Homo sapiens	Protein kinase C theta	IC50	2500.0	nM	10.1021/acs.jmedchem.0c01271
Homo sapiens	Protein kinase C theta	Inhibition	50.0	%	10.1021/acs.jmedchem.0c01271
Homo sapiens	Pyruvate dehydrogenase kinase isoform 1	Inhibition	6.0	%	10.1042/0264-6021:3510095
Homo sapiens	Ribosomal protein S6 kinase 1	Inhibition	49.0	%	10.1042/0264-6021:3510095
Homo sapiens	Ribosomal protein S6 kinase alpha 5	Inhibition	62.0	%	10.1042/0264-6021:3510095
Homo sapiens	Serine/threonine-protein kinase AKT	Inhibition	65.0	%	10.1042/0264-6021:3510095
Homo sapiens	Serine/threonine-protein kinase Chk1	Inhibition	4.0	%	10.1042/0264-6021:3510095
Homo sapiens	Serine/threonine-protein kinase Sgk1	Inhibition	28.0	%	10.1042/0264-6021:3510095
Homo sapiens	Tyrosine-protein kinase JAK3	IC50	61.0	nM	10.1016/j.bmcl.2009.04.039
Homo sapiens	Tyrosine-protein kinase LCK	Inhibition	68.0	%	10.1042/0264-6021:3510095
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	2818.4	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	3162.3	nM	None
Homo sapiens	Zinc finger protein GLI1	IC50	1800.0	nM	10.1021/jm801420y
Homo sapiens	Zinc finger protein GLI2	IC50	2700.0	nM	10.1021/jm801420y
Mus musculus	B16	IC50	4800.0	nM	10.1021/jm9603779
Mus musculus	Mus musculus	Mean survival in days	11.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	Mean survival in days	11.5	None	10.1021/jm9603779
Mus musculus	Mus musculus	Mean survival in days	23.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	Mean survival in days	26.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	Mean survival in days	30.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	T/C x100	94.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	T/C x100	100.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	T/C x100	104.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	T/C x100	106.0	None	10.1021/jm9603779
Mus musculus	Mus musculus	T/C x100	122.0	None	10.1021/jm9603779
Mus musculus	P388	IC50	4000.0	nM	10.1021/jm9603779
Mus musculus	Splenocyte	IC50	nan	nM	10.1016/S0960-894X(01)80995-1
Mus musculus	Transcription factor HES-1	Inhibition	nan	%	10.1016/j.bmcl.2009.07.146
Rattus norvegicus	Choline acetylase	Control	162.0	%	10.1016/0960-894X(95)00188-Y
Rattus norvegicus	Protein kinase C (PKC)	IC50	680.0	nM	10.1016/S0960-894X(01)80995-1
Rattus norvegicus	Rho-associated protein kinase 2	Inhibition	19.0	%	10.1042/0264-6021:3510095
Thermus thermophilus	Malate dehydrogenase	IC50	8000.0	nM	10.1021/jm020427b
None	NON-PROTEIN TARGET	IC50	1720.0	nM	10.1016/j.bmc.2016.05.032
None	Unchecked	IC50	8000.0	nM	10.1021/acs.jmedchem.7b01231
None	Unchecked	IC50	8000.0	nM	10.1021/jm020427b
None	Unchecked	IC50	25700.0	nM	10.1021/acs.jmedchem.7b01231
None	Unchecked	IC50	25700.0	nM	10.1021/jm9603779
None	Unchecked	Inhibition	0.0	%	10.1042/0264-6021:3510095
None	Unchecked	Inhibition	29.0	%	10.1042/0264-6021:3510095
None	Unchecked	Inhibition	30.0	%	10.1042/0264-6021:3510095
None	Unchecked	Inhibition	59.0	%	10.1042/0264-6021:3510095
None	Unchecked	Inhibition	99.0	%	10.1042/0264-6021:3510095
None	Unchecked	Potency	2685.9	nM	None
None	Unchecked	Potency	3548.1	nM	None
None	Unchecked	Potency	3981.1	nM	None

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT015180	Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3C[C@@H](N)[C@@H](O)[C@H](C)O3)O2)c(=O)[nH]c1=O.O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21>>C[C@@H]1O[C@@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@H](N)[C@H]1O	RXN-10931
AKRT015199	Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3C[C@](O)(C(=O)O)[C@H](C)O3)O2)c(=O)[nH]c1=O.O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21>>C[C@@H]1OC(n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@]1(O)C(=O)O	RXN-10926
AKRT015208	Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)O2)c(=O)[nH]c1=O.O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21>>C[C@@H]1OC(n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)[C@H](O)[C@H](O)[C@H]1O	RXN-10925
AKRT023267	O=C(O)c1[nH]c(C(=O)O)c(-c2c[nH]c3ccccc23)c1-c1c[nH]c2ccccc12>>O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21	RXN-10924
AKRT023601	O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C1NCc2c1c1c3ccccc3n([C@H]3O[C@H](CO)[C@@H](O)[C@H](O)C3O)c1c1[nH]c3ccccc3c21	enzymemap_85955