NP-MRD: Showing NP-Card for (5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol (NP0256591)

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Record Information

Version

2.0

Created at

2022-09-07 21:28:29 UTC

Updated at

2022-09-07 21:28:29 UTC

NP-MRD ID

NP0256591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

Description

CHEMBL3291072 belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. (5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol is found in Fridericia platyphylla. Based on a literature review very few articles have been published on CHEMBL3291072.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223282D          

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M  END

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  Mrv1652309072223282D          

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 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 19 37  1  0  0  0  0
 37 38  1  6  0  0  0
  8 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC2=C1[C@@H](\C=C\C1=CC=CC=C1)[C@@H]1[C@H](OC3=CC(O)=CC(OC)=C3[C@@H]1O2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O6/c1-35-24-15-21(33)17-26-28(24)23(14-13-19-9-5-3-6-10-19)29-31(20-11-7-4-8-12-20)37-27-18-22(34)16-25(36-2)30(27)32(29)38-26/h3-18,23,29,31-34H,1-2H3/b14-13+/t23-,29-,31-,32-/m1/s1

> <INCHI_KEY>
YMZLDTUSRCHDNT-YNIFFJEOSA-N

> <FORMULA>
C32H28O6

> <MOLECULAR_WEIGHT>
508.57

> <EXACT_MASS>
508.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
54.789999218105415

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,11S,11aR,12S)-1,6-dimethoxy-11-phenyl-12-[(E)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

> <JCHEM_LOGP>
6.307534403666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.688623513219436

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.086168654942593

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2886428938216

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
145.35120000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,11S,11aR,12S)-1,6-dimethoxy-11-phenyl-12-[(E)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.482   1.661   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.986  -3.868   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.514   2.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   2.534   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.498   3.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.986   4.281   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.482   5.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.490   6.900   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.506   5.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.035   3.117   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.522   3.408   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.018   4.863   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.027   6.027   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.539   5.736   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.043   4.281   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.051   1.370   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      18.084  -2.122   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.043  -3.868   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.531  -3.577   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.027  -2.122   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   38                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   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   20   37                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   20   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   28   37                                                  
CONECT   37   36   19   38                                                  
CONECT   38   37    8                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₈O₆

Average Mass

508.5700 Da

Monoisotopic Mass

508.18859 Da

IUPAC Name

(5aR,11S,11aR,12S)-1,6-dimethoxy-11-phenyl-12-[(E)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

Traditional Name

(5aR,11S,11aR,12S)-1,6-dimethoxy-11-phenyl-12-[(E)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1[C@@H](\C=C\C1=CC=CC=C1)[C@@H]1[C@H](OC3=CC(O)=CC(OC)=C3[C@@H]1O2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H28O6/c1-35-24-15-21(33)17-26-28(24)23(14-13-19-9-5-3-6-10-19)29-31(20-11-7-4-8-12-20)37-27-18-22(34)16-25(36-2)30(27)32(29)38-26/h3-18,23,29,31-34H,1-2H3/b14-13+/t23-,29-,31-,32-/m1/s1

InChI Key

YMZLDTUSRCHDNT-YNIFFJEOSA-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
Arrabidaea brachypoda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Anisole
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen 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	6.31	ChemAxon
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-4.3	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	5	ChemAxon
Refractivity	145.35 m³·mol⁻¹	ChemAxon
Polarizability	54.79 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

34219025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90682495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol (NP0256591)

MOL for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D MOL for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D SDF for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D-SDF for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

PDB for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D PDB for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

SMILES for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

INCHI for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

Structure for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D Structure for NP0256591 ((5ar,11s,11ar,12s)-1,6-dimethoxy-11-phenyl-12-[(1e)-2-phenylethenyl]-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)