NP-MRD: Showing NP-Card for 3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one (NP0204850)

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Record Information

Version

2.0

Created at

2022-09-05 00:37:35 UTC

Updated at

2022-09-05 00:37:35 UTC

NP-MRD ID

NP0204850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one

Description

3-({6-[2-(Dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one is found in Fumaria densiflora. 3-({6-[2-(Dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500422D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004261500422D          

 38 42  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 10 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  7 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(C(=O)N(CCC3=CC=CC=C3)C2(O)CC2=CC3=C(OCO3)C=C2CCN(C)C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H34N2O6/c1-31(2)14-13-21-16-25-26(38-19-37-25)17-22(21)18-30(34)23-10-11-24(35-3)28(36-4)27(23)29(33)32(30)15-12-20-8-6-5-7-9-20/h5-11,16-17,34H,12-15,18-19H2,1-4H3

> <INCHI_KEY>
HFYGXQFCFQNRAX-UHFFFAOYSA-N

> <FORMULA>
C30H34N2O6

> <MOLECULAR_WEIGHT>
518.61

> <EXACT_MASS>
518.241686823

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.6877044944412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
4.2280646583333334

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.106119130605498

> <JCHEM_PKA_STRONGEST_BASIC>
9.100737444297076

> <JCHEM_POLAR_SURFACE_AREA>
80.7

> <JCHEM_REFRACTIVITY>
145.4585

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      11.411  -3.397   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.106  -1.888   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.647  -1.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.342   0.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.883   0.604   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.728  -0.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.032  -1.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.690  -2.680   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.513  -4.210   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.557  -1.637   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.047  -1.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.556  -3.401   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.046  -3.706   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.555  -5.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.955  -5.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.973  -4.315   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.482  -2.855   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.028  -2.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.881   0.561   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       6.531   6.693   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.492  -2.415   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.796  -3.925   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.255  -4.416   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   10    6   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    7    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄N₂O₆

Average Mass

518.6100 Da

Monoisotopic Mass

518.24169 Da

IUPAC Name

3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

Traditional Name

3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C(=O)N(CCC3=CC=CC=C3)C2(O)CC2=CC3=C(OCO3)C=C2CCN(C)C)=C1OC

InChI Identifier

InChI=1S/C30H34N2O6/c1-31(2)14-13-21-16-25-26(38-19-37-25)17-22(21)18-30(34)23-10-11-24(35-3)28(36-4)27(23)29(33)32(30)15-12-20-8-6-5-7-9-20/h5-11,16-17,34H,12-15,18-19H2,1-4H3

InChI Key

HFYGXQFCFQNRAX-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
Fumaria densiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Benzodioxole
Isoindole
Phenethylamine
Anisole
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Lactam
Amino acid or derivatives
Carboxamide group
Oxacycle
Azacycle
Alkanolamine
Acetal
Ether
Carboxylic acid derivative
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen 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	3.33	ALOGPS
logP	4.23	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.7 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	145.46 m³·mol⁻¹	ChemAxon
Polarizability	56.69 Å³	ChemAxon
Number of Rings	5	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

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 3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one (NP0204850)

MOL for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

3D MOL for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

3D SDF for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

3D-SDF for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

PDB for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

3D PDB for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

SMILES for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

INCHI for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

Structure for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)

3D Structure for NP0204850 (3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methyl)-3-hydroxy-6,7-dimethoxy-2-(2-phenylethyl)isoindol-1-one)