NP-MRD: Showing NP-Card for 1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione (NP0151954)

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Record Information

Version

2.0

Created at

2022-09-02 08:21:05 UTC

Updated at

2022-09-02 08:21:05 UTC

NP-MRD ID

NP0151954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione

Description

1,4-Bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]-2H,3H,5H-benzo[e]indole-2,5-dione belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. 1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione is found in Iotrochota baculifera. 1,4-Bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]-2H,3H,5H-benzo[e]indole-2,5-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521152D          

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M  END

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M  END


  Mrv1533004231521152D          

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    7.0422   -1.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 24  1  0  0  0  0
 17 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 25 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 33 40  1  0  0  0  0
  5 41  1  0  0  0  0
 41 42  2  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CCN2C(=O)C(=C3C2=C(C2=CC=C(O)C(O)=C2)C(=O)C2=CC(O)=C(O)C=C32)C2=CC=C(O)C(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H23NO9/c34-18-5-1-15(2-6-18)9-10-33-30-28(17-4-8-22(36)24(38)12-17)31(41)20-14-26(40)25(39)13-19(20)29(30)27(32(33)42)16-3-7-21(35)23(37)11-16/h1-8,11-14,34-40H,9-10H2

> <INCHI_KEY>
BOYSXATUCQEFBT-UHFFFAOYSA-N

> <FORMULA>
C32H23NO9

> <MOLECULAR_WEIGHT>
565.534

> <EXACT_MASS>
565.137281325

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
58.53456502261355

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]-2H,3H,5H-benzo[e]indole-2,5-dione

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.9653863869999997

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.388789945124412

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.61358920162657

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5146837360816465

> <JCHEM_POLAR_SURFACE_AREA>
178.98999999999998

> <JCHEM_REFRACTIVITY>
154.44639999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0      14.048  -4.525   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.872  -3.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.423  -4.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.247  -3.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.520  -1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.344  -0.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.719  -0.076   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.228  -3.205   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.745   0.674   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.307  -3.109   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.846  -3.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.657  -4.370   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.929  -5.727   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.741  -7.036   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.390  -5.775   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.662  -7.132   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.579  -4.466   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.039   3.538   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.561   3.968   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.193   5.463   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.305   6.529   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.938   8.025   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.784   6.099   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.896   7.165   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.151   4.604   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.969  -1.021   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.145  -2.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   41                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   12   17                                                  
CONECT   25   14   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33   11   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33                                                       
CONECT   41    5   42                                                       
CONECT   42   41    2                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₃NO₉

Average Mass

565.5340 Da

Monoisotopic Mass

565.13728 Da

IUPAC Name

1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]-2H,3H,5H-benzo[e]indole-2,5-dione

Traditional Name

1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CCN2C(=O)C(=C3C2=C(C2=CC=C(O)C(O)=C2)C(=O)C2=CC(O)=C(O)C=C32)C2=CC=C(O)C(O)=C2)C=C1

InChI Identifier

InChI=1S/C32H23NO9/c34-18-5-1-15(2-6-18)9-10-33-30-28(17-4-8-22(36)24(38)12-17)31(41)20-14-26(40)25(39)13-19(20)29(30)27(32(33)42)16-3-7-21(35)23(37)11-16/h1-8,11-14,34-40H,9-10H2

InChI Key

BOYSXATUCQEFBT-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

Species Name	Source	Reference
Iotrochota baculifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Indole or derivatives
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Vinylogous amide
Tertiary carboxylic acid amide
Pyrroline
Carboxamide group
Ketone
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen 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	3.95	ALOGPS
logP	3.97	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	154.45 m³·mol⁻¹	ChemAxon
Polarizability	58.53 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione (NP0151954)

MOL for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

3D MOL for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

3D SDF for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

3D-SDF for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

PDB for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

3D PDB for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

SMILES for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

INCHI for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

Structure for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)

3D Structure for NP0151954 (1,4-bis(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-[2-(4-hydroxyphenyl)ethyl]benzo[e]indole-2,5-dione)