NP-MRD: Showing NP-Card for (+)-Staurosporine (NP0062054)

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Record Information

Version

1.0

Created at

2022-04-28 06:44:02 UTC

Updated at

2022-04-28 06:44:02 UTC

NP-MRD ID

NP0062054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Staurosporine

Description

Staurosporine, also known as STS, belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. It belongs to the most frequently isolated group of indolocarbazoles: Indolo(2,3-a)carbazoles. Staurosporine is a very strong basic compound (based on its pKa). Glucose is transformed to NTP-L-ristoamine by StaA/B/E/J/I/K which is then added on to the staurosporine aglycone at 1 indole N by StaG. This is followed by a nucleophilic attack between the indole nitrogens resulting in cyclization and then decarboxylation assisted by StaC exclusively forming staurosporine aglycone or K252c. (+)-Staurosporine is found in Eudistoma toealensis, Lycogala epidendrum, Micromonospora sp. L-31-CLCO-002 (CECT3347), Monobiceros langi, Saccharothrix aerocolonigenes subsp. copiosa SCC1951, Streptomyces actuosus, Streptomyces bingchenggensis, Streptomyces hygroscopicus, Streptomyces hygroscopicus C39280-450-9 (ATCC53730), Streptomyces lividus ATCC21178, Streptomyces longisporoflavus, Streptomyces longisporoflavus R-19 (DSM10189), Streptomyces platensis, Streptomyces platensis subsp. malvinus RK-1409, Streptomyces sanyensis, Streptomyces sp .N-128, Streptomyces sp. AB1869R-359 (NRRL B-16735), Streptomyces sp. AM-2282, Streptomyces sp. C-71799, Streptomyces sp. KS3, Streptomyces sp. M-193, Streptomyces sp. N-115, Streptomyces sp. N-126, Streptomyces sp. N-129, Streptomyces sp. N-71, Streptomyces sp. N96C-47, Streptomyces sp. RK-286, Streptomyces sp. TP-A0274, Streptomyces staurosporeus AM-2282 and Streptomyces staurosporininus. The main biological activity of staurosporine is the inhibition of protein kinases through the prevention of ATP binding to the kinase.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041411302D          

 38 45  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05041411302D          

 38 45  0  0  1  0            999 V2000
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 26 17  1  0  0  0  0
 27 23  1  0  0  0  0
 28  1  1  6  0  0  0
 28 26  1  0  0  0  0
 29  2  1  0  0  0  0
 17 29  1  1  0  0  0
 30 13  1  0  0  0  0
 30 27  1  0  0  0  0
 31 18  1  0  0  0  0
 31 20  1  0  0  0  0
 31 24  1  0  0  0  0
 32 19  1  0  0  0  0
 32 25  1  0  0  0  0
 32 28  1  0  0  0  0
 33 27  2  0  0  0  0
 34  3  1  0  0  0  0
 26 34  1  1  0  0  0
 35 20  1  0  0  0  0
 35 28  1  0  0  0  0
 17 36  1  6  0  0  0
 20 37  1  6  0  0  0
 26 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0062054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C[C@@]2([H])O[C@](C)(N3C4=CC=CC=C4C4=C5CNC(=O)C5=C5C6=CC=CC=C6N2C5=C34)[C@]1([H])OC)NC

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
HKSZLNNOFSGOKW-FYTWVXJKSA-N

> <FORMULA>
C28H26N4O3

> <MOLECULAR_WEIGHT>
466.531

> <EXACT_MASS>
466.200490718

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.47314305361091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,6R)-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

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.969673164333333

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.47811317441846

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.144814219414428

> <JCHEM_PKA_STRONGEST_BASIC>
9.55360394965467

> <JCHEM_POLAR_SURFACE_AREA>
69.45

> <JCHEM_REFRACTIVITY>
132.37209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,6R)-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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   28                                                            
CONECT    2   29                                                            
CONECT    3   34                                                            
CONECT    4    6    8                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8    4   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   18                                                       
CONECT   11    7   19                                                       
CONECT   12   17   20                                                       
CONECT   13   16   30                                                       
CONECT   14    8   18   22                                                  
CONECT   15    9   19   21                                                  
CONECT   16   13   21   23                                                  
CONECT   17   12   26   29   36                                             
CONECT   18   10   14   31                                                  
CONECT   19   11   15   32                                                  
CONECT   20   12   31   35   37                                             
CONECT   21   15   16   25                                                  
CONECT   22   14   23   24                                                  
CONECT   23   16   22   27                                                  
CONECT   24   22   25   31                                                  
CONECT   25   21   24   32                                                  
CONECT   26   17   28   34   38                                             
CONECT   27   23   30   33                                                  
CONECT   28    1   26   32   35                                             
CONECT   29    2   17                                                       
CONECT   30   13   27                                                       
CONECT   31   18   20   24                                                  
CONECT   32   19   25   28                                                  
CONECT   33   27                                                            
CONECT   34    3   26                                                       
CONECT   35   20   28                                                       
CONECT   36   17                                                            
CONECT   37   20                                                            
CONECT   38   26                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   90    0
END

View in JSmol

Synonyms

Value	Source
(+)-Staurosporine	ChEBI
Staurosporin	ChEBI
STS	ChEBI

Chemical Formula

C₂₈H₂₆N₄O₃

Average Mass

466.5310 Da

Monoisotopic Mass

466.20049 Da

IUPAC Name

(2S,3R,4R,6R)-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

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[C@@]2([H])O[C@](C)(N3C4=CC=CC=C4C4=C5CNC(=O)C5=C5C6=CC=CC=C6N2C5=C34)[C@]1([H])OC)NC

InChI Identifier

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

InChI Key

HKSZLNNOFSGOKW-FYTWVXJKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eudistoma toealensis	Animalia	KNApSAcK
Lycogala epidendrum	LOTUS Database	35616633
Micromonospora sp. L-31-CLCO-002 (CECT3347)	Bacteria	KNApSAcK
Monobiceros langi	LOTUS Database	35616633
Saccharothrix aerocolonigenes subsp. copiosa SCC1951	-	KNApSAcK
Streptomyces actuosus	Bacteria	KNApSAcK
Streptomyces bingchenggensis	LOTUS Database	35616633
Streptomyces hygroscopicus	LOTUS Database	35616633
Streptomyces hygroscopicus C39280-450-9 (ATCC53730)	Bacteria	KNApSAcK
Streptomyces lividus ATCC21178	Bacteria	KNApSAcK
Streptomyces longisporoflavus	Bacteria	KNApSAcK
Streptomyces longisporoflavus R-19 (DSM10189)	Bacteria	KNApSAcK
Streptomyces platensis	LOTUS Database	35616633
Streptomyces platensis subsp. malvinus RK-1409	Bacteria	KNApSAcK
Streptomyces sanyensis	LOTUS Database	35616633
Streptomyces sp .N-128	Bacteria	KNApSAcK
Streptomyces sp. AB1869R-359 (NRRL B-16735)	Bacteria	KNApSAcK
Streptomyces sp. AM-2282	Bacteria	KNApSAcK
Streptomyces sp. C-71799	Bacteria	KNApSAcK
Streptomyces sp. KS3	Bacteria	KNApSAcK
Streptomyces sp. M-193	Bacteria	KNApSAcK
Streptomyces sp. N-115	Bacteria	KNApSAcK
Streptomyces sp. N-126	Bacteria	KNApSAcK
Streptomyces sp. N-129	Bacteria	KNApSAcK
Streptomyces sp. N-71	Bacteria	KNApSAcK
Streptomyces sp. N96C-47	Bacteria	KNApSAcK
Streptomyces sp. RK-286	Bacteria	KNApSAcK
Streptomyces sp. TP-A0274	Bacteria	KNApSAcK
Streptomyces staurosporeus AM-2282	Bacteria	KNApSAcK
Streptomyces staurosporininus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Pyrroloindole
Isoindolone
Indole
Isoindoline
Isoindole or derivatives
Benzenoid
Oxane
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Secondary amine
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterooctacyclic compound (CHEBI:15738 )
indolocarbazole alkaloid (CHEBI:15738 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.14	ALOGPS
logP	3.97	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.14	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.37 m³·mol⁻¹	ChemAxon
Polarizability	50.47 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB02010

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018127

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Staurosporine

METLIN ID

Not Available

PubChem Compound

44259

PDB ID

Not Available

ChEBI ID

15738

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Staurosporine (NP0062054)

MOL for NP0062054 ((+)-Staurosporine)

3D MOL for NP0062054 ((+)-Staurosporine)

3D SDF for NP0062054 ((+)-Staurosporine)

3D-SDF for NP0062054 ((+)-Staurosporine)

PDB for NP0062054 ((+)-Staurosporine)

3D PDB for NP0062054 ((+)-Staurosporine)

SMILES for NP0062054 ((+)-Staurosporine)

INCHI for NP0062054 ((+)-Staurosporine)

Structure for NP0062054 ((+)-Staurosporine)

3D Structure for NP0062054 ((+)-Staurosporine)