NP-MRD: Showing NP-Card for (1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol (NP0171960)

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Record Information

Version

2.0

Created at

2022-09-03 08:41:46 UTC

Updated at

2022-09-03 08:41:47 UTC

NP-MRD ID

NP0171960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol

Description

(1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-3,3a-diol 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,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol is found in Aglaia odorata. Based on a literature review very few articles have been published on (1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-3,3a-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210412D          

 34 38  0  0  1  0            999 V2000
    4.8010    2.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370    2.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335    2.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    1.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267    2.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907    3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    4.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    4.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1941    3.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    2.6853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2722    3.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441    3.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3603    4.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3892    1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032210412D          

 34 38  0  0  1  0            999 V2000
    4.8010    2.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0171960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1)[C@]1(O)[C@H](O)C[C@@H](C3=CC=CC=C3)[C@@]1(C2)C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O6/c1-31-20-12-18-16-27(19-10-11-22(32-2)23(13-19)33-3)21(17-8-6-5-7-9-17)15-25(29)28(27,30)26(18)24(14-20)34-4/h5-14,21,25,29-30H,15-16H2,1-4H3/t21-,25+,27+,28+/m0/s1

> <INCHI_KEY>
XIIWVZRHQQMJBE-JLGHAOBZSA-N

> <FORMULA>
C28H30O6

> <MOLECULAR_WEIGHT>
462.542

> <EXACT_MASS>
462.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.053472242704665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-3,3a-diol

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.681505499

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.648389218935964

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.535821646135322

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3149280096172786

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
128.63730000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-3,3a-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.962   5.057   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.909   3.933   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.409   4.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.356   3.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.857   3.508   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.410   4.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.463   6.106   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.016   7.580   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.068   8.704   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.962   5.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.870   5.012   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.375   6.467   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.642   5.942   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.673   7.482   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.621   5.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.174   3.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.438   2.707   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.307   1.173   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.571   0.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.965   0.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.096   2.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.832   3.361   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.365   3.558   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.335   2.018   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.653   1.222   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.623  -0.318   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.274  -1.062   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.244  -2.601   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.562  -3.397   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.044  -0.265   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.393  -1.009   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.423  -2.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.014   1.274   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.593   2.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3                                                       
CONECT   11    6   12   13   23                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   16   11   24   34                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   24                                                       
CONECT   34   23    5                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₆

Average Mass

462.5420 Da

Monoisotopic Mass

462.20424 Da

IUPAC Name

(1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,3aH,8H,8aH-cyclopenta[a]indene-3,3a-diol

Traditional Name

(1S,3R,3aS,8aS)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1H,2H,3H,8H-cyclopenta[a]indene-3,3a-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1)[C@]1(O)[C@H](O)C[C@@H](C3=CC=CC=C3)[C@@]1(C2)C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C28H30O6/c1-31-20-12-18-16-27(19-10-11-22(32-2)23(13-19)33-3)21(17-8-6-5-7-9-17)15-25(29)28(27,30)26(18)24(14-20)34-4/h5-14,21,25,29-30H,15-16H2,1-4H3/t21-,25+,27+,28+/m0/s1

InChI Key

XIIWVZRHQQMJBE-JLGHAOBZSA-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
Dimethoxybenzene
O-dimethoxybenzene
Indane
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
1,2-diol
Ether
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	3.96	ALOGPS
logP	3.68	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.64 m³·mol⁻¹	ChemAxon
Polarizability	50.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162852795

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol (NP0171960)

MOL for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

3D MOL for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

3D SDF for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

3D-SDF for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

PDB for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

3D PDB for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

SMILES for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

INCHI for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

Structure for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)

3D Structure for NP0171960 ((1s,3r,3as,8as)-8a-(3,4-dimethoxyphenyl)-4,6-dimethoxy-1-phenyl-1h,2h,3h,8h-cyclopenta[a]indene-3,3a-diol)