NP-MRD: Showing NP-Card for (5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol (NP0180062)

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Record Information

Version

2.0

Created at

2022-09-03 18:21:50 UTC

Updated at

2022-09-03 18:21:50 UTC

NP-MRD ID

NP0180062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

Description

CHEMBL3291071 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-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-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 CHEMBL3291071.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220212D          

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M  END

     RDKit          3D

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  Mrv1652309032220212D          

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    1.3502   -5.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2700   -6.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.6655    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 38 31  1  1  0  0  0
  9 38  1  0  0  0  0
 20 38  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  2  0  0  0  0
  3 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\[C@H]2[C@@H]3[C@H](OC4=CC(O)=CC(OC)=C4[C@@H]3OC3=CC(O)=CC(OC)=C23)C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O7/c1-36-23-12-9-19(10-13-23)11-14-24-29-25(37-2)15-21(34)17-27(29)40-33-30(24)32(20-7-5-4-6-8-20)39-28-18-22(35)16-26(38-3)31(28)33/h4-18,24,30,32-35H,1-3H3/b14-11+/t24-,30-,32-,33-/m1/s1

> <INCHI_KEY>
NTMAFGPMRMTODT-BIJDMMQYSA-N

> <FORMULA>
C33H30O7

> <MOLECULAR_WEIGHT>
538.596

> <EXACT_MASS>
538.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.967260676752744

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,11S,11aR,12S)-1,6-dimethoxy-12-[(E)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

> <JCHEM_LOGP>
6.149863138

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.68862351321939

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.086168654942556

> <JCHEM_PKA_STRONGEST_BASIC>
-4.177221543921802

> <JCHEM_POLAR_SURFACE_AREA>
86.61000000000001

> <JCHEM_REFRACTIVITY>
151.81439999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,11S,11aR,12S)-1,6-dimethoxy-12-[(E)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-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      -1.008 -17.219   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.016 -16.055   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.512 -14.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.520 -13.436   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.016 -11.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.504 -11.690   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000 -10.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.512  -9.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.008  -9.070   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.520  -9.361   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.016  -3.832   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.024  -5.578   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.041  -3.832   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.545  -2.377   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.082  -5.578   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.049  -9.070   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.537  -9.361   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.033 -10.817   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.041 -11.981   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.537 -13.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.024 -13.727   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.016 -12.563   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.520 -11.108   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.529  -8.197   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.504 -12.854   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000 -14.309   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   38                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   31    9   20                                                  
CONECT   39    6   40                                                       
CONECT   40   39    3                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₇

Average Mass

538.5960 Da

Monoisotopic Mass

538.19915 Da

IUPAC Name

(5aR,11S,11aR,12S)-1,6-dimethoxy-12-[(E)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

Traditional Name

(5aR,11S,11aR,12S)-1,6-dimethoxy-12-[(E)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\[C@H]2[C@@H]3[C@H](OC4=CC(O)=CC(OC)=C4[C@@H]3OC3=CC(O)=CC(OC)=C23)C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C33H30O7/c1-36-23-12-9-19(10-13-23)11-14-24-29-25(37-2)15-21(34)17-27(29)40-33-30(24)32(20-7-5-4-6-8-20)39-28-18-22(35)16-26(38-3)31(28)33/h4-18,24,30,32-35H,1-3H3/b14-11+/t24-,30-,32-,33-/m1/s1

InChI Key

NTMAFGPMRMTODT-BIJDMMQYSA-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
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	6.15	ChemAxon
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.81 m³·mol⁻¹	ChemAxon
Polarizability	57.97 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	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

34219024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90682494

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-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol (NP0180062)

MOL for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D MOL for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D SDF for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D-SDF for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

PDB for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D PDB for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

SMILES for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

INCHI for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

Structure for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)

3D Structure for NP0180062 ((5ar,11s,11ar,12s)-1,6-dimethoxy-12-[(1e)-2-(4-methoxyphenyl)ethenyl]-11-phenyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphene-3,8-diol)