NP-MRD: Showing NP-Card for 5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione (NP0155632)

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Record Information

Version

2.0

Created at

2022-09-02 12:43:55 UTC

Updated at

2022-09-02 12:43:55 UTC

NP-MRD ID

NP0155632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione

Description

12-Demethyl-12-oxo-eurotechinulin B belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on 12-demethyl-12-oxo-eurotechinulin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214432D          

 34 36  0  0  0  0            999 V2000
   -0.8857   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
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 16 22  1  0  0  0  0
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  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
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 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  2  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

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   -2.1189    1.2398    0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2355    3.6100   -1.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673    4.0003   -1.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241    4.3829   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954    4.0583   -2.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    1.6434    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279    0.3503    0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.4271    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024   -0.0249   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1962    2.8825   -2.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6809   -0.3465    2.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1182    1.5906    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022214432D          

 34 36  0  0  0  0            999 V2000
   -0.8857   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(CC=C(C)C)=C2N=C(C(=CC3=C(O)NC(=O)C(=O)N3)C2=C1)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H33N3O3/c1-8-28(6,7)24-21(15-22-25(32)31-27(34)26(33)29-22)20-14-18(11-9-16(2)3)13-19(23(20)30-24)12-10-17(4)5/h8-10,13-15H,1,11-12H2,2-7H3,(H,29,33)(H2,31,32,34)

> <INCHI_KEY>
QBHLUAIWFDJXQG-UHFFFAOYSA-N

> <FORMULA>
C28H33N3O3

> <MOLECULAR_WEIGHT>
459.59

> <EXACT_MASS>
459.252191935

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.2714808408718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-3H-indol-3-ylidene]methyl}-6-hydroxy-1,2,3,4-tetrahydropyrazine-2,3-dione

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
6.710850616679058

> <ALOGPS_LOGS>
-5.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.4322563415961564

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.803658062631699

> <JCHEM_PKA_STRONGEST_BASIC>
8.198557507624326

> <JCHEM_POLAR_SURFACE_AREA>
90.78999999999999

> <JCHEM_REFRACTIVITY>
151.63620000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.653  -3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   4.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.857   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.259   0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       4.187  -4.838   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       5.217  -5.982   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.723  -5.662   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.741  -7.447   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.772  -8.591   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0       3.235  -7.767   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22    8   24                                                  
CONECT   24   23    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃N₃O₃

Average Mass

459.5900 Da

Monoisotopic Mass

459.25219 Da

IUPAC Name

5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-3H-indol-3-ylidene]methyl}-6-hydroxy-1,2,3,4-tetrahydropyrazine-2,3-dione

Traditional Name

5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC(CC=C(C)C)=C2N=C(C(=CC3=C(O)NC(=O)C(=O)N3)C2=C1)C(C)(C)C=C

InChI Identifier

InChI=1S/C28H33N3O3/c1-8-28(6,7)24-21(15-22-25(32)31-27(34)26(33)29-22)20-14-18(11-9-16(2)3)13-19(23(20)30-24)12-10-17(4)5/h8-10,13-15H,1,11-12H2,2-7H3,(H,29,33)(H2,31,32,34)

InChI Key

QBHLUAIWFDJXQG-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Benzenoid
Pyrazine
Heteroaromatic compound
Lactam
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
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	5.33	ALOGPS
logP	6.71	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
pKa (Strongest Basic)	8.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.79 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	151.64 m³·mol⁻¹	ChemAxon
Polarizability	53.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

136866274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione (NP0155632)

MOL for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

3D MOL for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

3D SDF for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

3D-SDF for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

PDB for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

3D PDB for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

SMILES for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

INCHI for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

Structure for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)

3D Structure for NP0155632 (5-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)indol-3-ylidene]methyl}-6-hydroxy-1,4-dihydropyrazine-2,3-dione)