NP-MRD: Showing NP-Card for 1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone (NP0302768)

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Record Information

Version

2.0

Created at

2022-09-10 16:33:35 UTC

Updated at

2022-09-10 16:33:35 UTC

NP-MRD ID

NP0302768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

Description

Fredericamycin, also known as FCRC-a48, belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. 1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone is found in Streptomyces griseus. 1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone was first documented in 2020 (PMID: 32999145). Based on a literature review a small amount of articles have been published on Fredericamycin (PMID: 32025682) (PMID: 34377413) (PMID: 33522232) (PMID: 32481766).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218332D          

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M  END

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M  END


  Mrv1652309102218332D          

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 10 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 26 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 23 38  1  0  0  0  0
 38 39  2  0  0  0  0
 18 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302768

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(C(=O)C3=C(O)C4(CCC5=CC6=CC(\C=C\C=C\C)=NC(O)=C6C(O)=C45)C(O)=C3C2=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,36-38H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+

> <INCHI_KEY>
NJLAGDPRCAPJIF-VNKDHWASSA-N

> <FORMULA>
C30H21NO9

> <MOLECULAR_WEIGHT>
539.496

> <EXACT_MASS>
539.12163126

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.51964093228237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,1',3,9'-tetrahydroxy-7-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-4,5,6',7',8,9-hexahydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

> <JCHEM_LOGP>
2.683203527666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.234400931129452

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6812606466671416

> <JCHEM_PKA_STRONGEST_BASIC>
5.523866777962565

> <JCHEM_POLAR_SURFACE_AREA>
171.32

> <JCHEM_REFRACTIVITY>
148.88959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,1',3,9'-tetrahydroxy-7-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      18.543  -3.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.052  -3.354   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.641  -1.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.150  -1.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.738  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.247   0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.836   1.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345   2.254   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.933   3.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.442   4.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.363   3.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.774   1.541   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.695   0.443   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.265   1.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.677  -0.328   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.598  -1.427   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      12.168  -0.714   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.985   3.712   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.212   5.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.731   5.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.757   2.189   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.855   1.110   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.238   1.935   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.411   0.636   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.122  -0.730   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.872   0.703   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.045  -0.596   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.756  -1.962   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.506  -0.529   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.205   0.837   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.743   0.904   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.571  -0.395   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.623   2.136   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.089   3.502   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.161   2.069   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.988   3.368   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.277   4.734   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.527   3.301   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.606   4.399   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.352   5.918   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6                                                       
CONECT   18   11   19   21   39                                             
CONECT   19   18   20                                                       
CONECT   20   19   10                                                       
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   38                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   35                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   23   39                                                  
CONECT   39   38   18   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
FCRC-a48	MeSH
Fredericamycin a	MeSH

Chemical Formula

C₃₀H₂₁NO₉

Average Mass

539.4960 Da

Monoisotopic Mass

539.12163 Da

IUPAC Name

1,1',3,9'-tetrahydroxy-7-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-4,5,6',7',8,9-hexahydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

Traditional Name

1,1',3,9'-tetrahydroxy-7-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(C(=O)C3=C(O)C4(CCC5=CC6=CC(\C=C\C=C\C)=NC(O)=C6C(O)=C45)C(O)=C3C2=O)C1=O

InChI Identifier

InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,36-38H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+

InChI Key

NJLAGDPRCAPJIF-VNKDHWASSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Naphthalene
Isoquinoline
Indene
Indane
Anisole
1-hydroxy-4-unsubstituted benzenoid
Hydroxypyridine
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Azacycle
Polyol
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.68	ChemAxon
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	5.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	171.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.89 m³·mol⁻¹	ChemAxon
Polarizability	55.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018380

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135430424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujioka H: Development of New Innovative Synthetic Organic Chemistry Using Lone Pairs of Oxygen Atoms. Chem Pharm Bull (Tokyo). 2020;68(10):907-945. doi: 10.1248/cpb.c20-00178. [PubMed:32999145 ]
Najera C, Foubelo F, Sansano JM, Yus M: Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds. Org Biomol Chem. 2020 Feb 19;18(7):1279-1336. doi: 10.1039/c9ob02597a. [PubMed:32025682 ]
Wang FX, Yan JL, Liu Z, Zhu T, Liu Y, Ren SC, Lv WX, Jin Z, Chi YR: Assembly of multicyclic isoquinoline scaffolds from pyridines: formal total synthesis of fredericamycin A. Chem Sci. 2021 Jun 28;12(30):10259-10265. doi: 10.1039/d1sc02442f. eCollection 2021 Aug 4. [PubMed:34377413 ]
Kita Y, Akai S, Fujioka H, Kamitanaka T: 1-Alkoxyvinyl Ester as an Excellent Acyl Donor: Efficient Macrolactone Synthesis. J Org Chem. 2021 Mar 5;86(5):3683-3696. doi: 10.1021/acs.joc.0c02677. Epub 2021 Jan 31. [PubMed:33522232 ]
Rodriguez Estevez M, Myronovskyi M, Rosenkranzer B, Paululat T, Petzke L, Ristau J, Luzhetskyy A: Novel Fredericamycin Variant Overproduced by a Streptomycin-resistant Streptomyces albus subsp. chlorinus Strain. Mar Drugs. 2020 May 28;18(6):284. doi: 10.3390/md18060284. [PubMed:32481766 ]
LOTUS database [Link]

Showing NP-Card for 1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone (NP0302768)

MOL for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

3D MOL for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

3D SDF for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

3D-SDF for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

PDB for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

3D PDB for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

SMILES for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

INCHI for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

Structure for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)

3D Structure for NP0302768 (1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1e,3e)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone)