NP-MRD: Showing NP-Card for 8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide (NP0164448)

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Record Information

Version

2.0

Created at

2022-09-02 23:19:34 UTC

Updated at

2022-09-02 23:19:35 UTC

NP-MRD ID

NP0164448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide

Description

8A-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboxamide belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide is found in Aglaia odorata. 8A-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboxamide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519242D          

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M  END

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M  END


  Mrv1533004161519242D          

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    3.9640    2.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4242    3.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    4.1061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5047    4.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140    3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741    3.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    3.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    2.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  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  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  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  3 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 30 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1)C1(O)C(O)C(C(C3=CC=CC=C3)C1(C2)C1=CC=C(OC)C(OC)=C1)C(=O)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H35NO7/c1-32(2)29(34)25-27(18-10-8-7-9-11-18)30(20-12-13-22(37-4)23(15-20)38-5)17-19-14-21(36-3)16-24(39-6)26(19)31(30,35)28(25)33/h7-16,25,27-28,33,35H,17H2,1-6H3

> <INCHI_KEY>
RFZDMRXQEZZIKZ-UHFFFAOYSA-N

> <FORMULA>
C31H35NO7

> <MOLECULAR_WEIGHT>
533.621

> <EXACT_MASS>
533.241352471

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.77656904244397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboxamide

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
2.70056699

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.234674952662392

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.468002080024476

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2782327938658082

> <JCHEM_POLAR_SURFACE_AREA>
97.69000000000001

> <JCHEM_REFRACTIVITY>
146.3388

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.719   0.346   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.666   1.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.650   2.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.417   1.814   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.571  -2.079   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.373   0.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.868  -1.065   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.228  -2.177   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.175  -3.301   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.319  -0.164   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.484   0.844   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       8.610  -1.676   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      10.065  -2.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.445  -2.684   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.681   2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.550   4.229   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.814   5.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.208   4.456   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.339   2.921   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.075   2.041   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.382   3.300   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.895   3.590   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.399   5.045   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.392   6.210   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.896   7.665   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.409   7.955   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.879   5.919   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.872   7.084   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.359   6.793   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.375   4.464   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12   30                                             
CONECT    8    7    9   24                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    3                                                       
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    8   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30    7   31   39                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   30                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₅NO₇

Average Mass

533.6210 Da

Monoisotopic Mass

533.24135 Da

IUPAC Name

8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboxamide

Traditional Name

8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-N,N-dimethyl-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-2-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1)C1(O)C(O)C(C(C3=CC=CC=C3)C1(C2)C1=CC=C(OC)C(OC)=C1)C(=O)N(C)C

InChI Identifier

InChI=1S/C31H35NO7/c1-32(2)29(34)25-27(18-10-8-7-9-11-18)30(20-12-13-22(37-4)23(15-20)38-5)17-19-14-21(36-3)16-24(39-6)26(19)31(30,35)28(25)33/h7-16,25,27-28,33,35H,17H2,1-6H3

InChI Key

RFZDMRXQEZZIKZ-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
Aglaia odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Monoterpenoid
11-noriridane monoterpenoid
Dimethoxybenzene
O-dimethoxybenzene
Aromatic monoterpenoid
Indane
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Tertiary alcohol
Cyclic alcohol
1,2-diol
Carboxamide group
Secondary alcohol
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.65	ALOGPS
logP	2.7	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.34 m³·mol⁻¹	ChemAxon
Polarizability	57.78 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 8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide (NP0164448)

MOL for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

3D MOL for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

3D SDF for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

3D-SDF for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

PDB for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

3D PDB for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

SMILES for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

INCHI for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

Structure for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)

3D Structure for NP0164448 (8a-(3,4-dimethoxyphenyl)-3,3a-dihydroxy-4,6-dimethoxy-n,n-dimethyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboxamide)