NP-MRD: Showing NP-Card for (1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid (NP0311670)

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Record Information

Version

2.0

Created at

2022-09-11 07:49:44 UTC

Updated at

2022-09-11 07:49:44 UTC

NP-MRD ID

NP0311670

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid

Description

(1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboximidic acid 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. (1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid is found in Aglaia odorata. Based on a literature review very few articles have been published on (1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209492D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112209492D          

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 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 14 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  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
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0311670

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(C[C@]3([C@@H]([C@H]([C@@H](O)[C@@]23O)C(O)=NC)C2=CC=CC=C2)C2=CC=C(OC)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO7/c1-30-27(33)23-25(16-8-6-5-7-9-16)28(18-10-11-21(36-3)20(31)13-18)15-17-12-19(35-2)14-22(37-4)24(17)29(28,34)26(23)32/h5-14,23,25-26,31-32,34H,15H2,1-4H3,(H,30,33)/t23-,25-,26-,28-,29+/m1/s1

> <INCHI_KEY>
DCOAOFKGFOXTMZ-HMGGBNILSA-N

> <FORMULA>
C29H31NO7

> <MOLECULAR_WEIGHT>
505.567

> <EXACT_MASS>
505.210052342

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.73754854570396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboximidic acid

> <JCHEM_LOGP>
0.5056820167935769

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.863231017826276

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.737173101653407

> <JCHEM_PKA_STRONGEST_BASIC>
11.849105786371505

> <JCHEM_POLAR_SURFACE_AREA>
120.97000000000003

> <JCHEM_REFRACTIVITY>
137.48150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.029  -5.116   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.484  -4.611   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.774  -3.099   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.610  -2.091   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.229  -2.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.676  -1.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.413  -0.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.018  -0.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.245  -0.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.114   1.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.280   2.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.543   1.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.216  -1.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.711   0.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.719   1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.214   2.984   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.702   3.275   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.197   4.730   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.205   5.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.694   2.110   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.345   2.854   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.199   0.655   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.444  -0.161   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.707  -1.041   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.207  -0.691   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.260  -1.815   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.759  -1.465   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.812  -2.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.813  -3.289   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.313  -3.639   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.866  -5.112   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.919  -6.236   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.260  -2.515   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.720  -2.545   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.225  -4.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.493  -3.475   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.523  -5.014   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   36                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6   14   23   34                                             
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   13   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   24   34                                                  
CONECT   34   33   13   35   36                                             
CONECT   35   34                                                            
CONECT   36   34    5   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,3AS,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,3ah,8H,8ah-cyclopenta[a]indene-2-carboximidate	Generator

Chemical Formula

C₂₉H₃₁NO₇

Average Mass

505.5670 Da

Monoisotopic Mass

505.21005 Da

IUPAC Name

(1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-2-carboximidic acid

Traditional Name

(1S,2R,3R,3aS,8aS)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-N-methyl-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(C[C@]3([C@@H]([C@H]([C@@H](O)[C@@]23O)C(O)=NC)C2=CC=CC=C2)C2=CC=C(OC)C(O)=C2)=C1

InChI Identifier

InChI=1S/C29H31NO7/c1-30-27(33)23-25(16-8-6-5-7-9-16)28(18-10-11-21(36-3)20(31)13-18)15-17-12-19(35-2)14-22(37-4)24(17)29(28,34)26(23)32/h5-14,23,25-26,31-32,34H,15H2,1-4H3,(H,30,33)/t23-,25-,26-,28-,29+/m1/s1

InChI Key

DCOAOFKGFOXTMZ-HMGGBNILSA-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
Methoxyphenol
Monoterpenoid
11-noriridane monoterpenoid
Aromatic monoterpenoid
Indane
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
1,2-diol
Secondary alcohol
Organic 1,3-dipolar compound
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Ether
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen 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	0.51	ChemAxon
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	11.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.48 m³·mol⁻¹	ChemAxon
Polarizability	53.74 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

162927379

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid (NP0311670)

MOL for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

3D MOL for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

3D SDF for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

3D-SDF for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

PDB for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

3D PDB for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

SMILES for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

INCHI for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

Structure for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)

3D Structure for NP0311670 ((1s,2r,3r,3as,8as)-3,3a-dihydroxy-8a-(3-hydroxy-4-methoxyphenyl)-4,6-dimethoxy-n-methyl-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-2-carboximidic acid)