NP-MRD: Showing NP-Card for Semecarpetin (NP0054364)

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Record Information

Version

2.0

Created at

2022-04-28 00:44:27 UTC

Updated at

2022-04-28 00:44:27 UTC

NP-MRD ID

NP0054364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Semecarpetin

Description

(2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Semecarpetin is found in Semecarpus anacardium and Semecarpus kurzii. Based on a literature review very few articles have been published on (2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202442D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282202442D          

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    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  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  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  2  0  0  0  0
 29 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 23 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C[C@H](O2)C1=CC=C(OC)C(=C1)C1=C(O)C=CC2=C1O[C@H](CC2=O)C1=CC(OC)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H30O9/c1-38-20-7-8-21-25(36)16-29(42-31(21)15-20)18-5-11-27(39-2)23(13-18)33-24(35)10-9-22-26(37)17-30(43-34(22)33)19-6-12-28(40-3)32(14-19)41-4/h5-15,29-30,35H,16-17H2,1-4H3/t29-,30+/m0/s1

> <INCHI_KEY>
PUZBENASFBKDLA-XZWHSSHBSA-N

> <FORMULA>
C34H30O9

> <MOLECULAR_WEIGHT>
582.605

> <EXACT_MASS>
582.188982546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
61.32419491953141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
4.931337192333333

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.485664441709833

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.487372002012674

> <JCHEM_PKA_STRONGEST_BASIC>
-4.186116093564071

> <JCHEM_POLAR_SURFACE_AREA>
109.75000000000001

> <JCHEM_REFRACTIVITY>
157.60609999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    9                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    3   21                                                       
CONECT   21   20                                                            
CONECT   22    2   23   27                                                  
CONECT   23   22   24   43                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   29   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36   40                                                       
CONECT   40   39                                                            
CONECT   41   35   42                                                       
CONECT   42   41                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀O₉

Average Mass

582.6050 Da

Monoisotopic Mass

582.18898 Da

IUPAC Name

(2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R)-2-(3,4-dimethoxyphenyl)-7-hydroxy-8-{2-methoxy-5-[(2S)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C(=O)C[C@H](O2)C1=CC=C(OC)C(=C1)C1=C(O)C=CC2=C1O[C@H](CC2=O)C1=CC(OC)=C(OC)C=C1

InChI Identifier

InChI=1S/C34H30O9/c1-38-20-7-8-21-25(36)16-29(42-31(21)15-20)18-5-11-27(39-2)23(13-18)33-24(35)10-9-22-26(37)17-30(43-34(22)33)19-6-12-28(40-3)32(14-19)41-4/h5-15,29-30,35H,16-17H2,1-4H3/t29-,30+/m0/s1

InChI Key

PUZBENASFBKDLA-XZWHSSHBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Semecarpus anacardium	Plant	KNApSAcK
Semecarpus kurzii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
7-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavanone
7-hydroxyflavonoid
Flavan
Chromone
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Benzopyran
Chromane
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.7	ALOGPS
logP	4.93	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	157.61 m³·mol⁻¹	ChemAxon
Polarizability	61.32 Å³	ChemAxon
Number of Rings	6	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

162981135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Semecarpetin (NP0054364)

MOL for NP0054364 (Semecarpetin)

3D MOL for NP0054364 (Semecarpetin)

3D SDF for NP0054364 (Semecarpetin)

3D-SDF for NP0054364 (Semecarpetin)

PDB for NP0054364 (Semecarpetin)

3D PDB for NP0054364 (Semecarpetin)

SMILES for NP0054364 (Semecarpetin)

INCHI for NP0054364 (Semecarpetin)

Structure for NP0054364 (Semecarpetin)

3D Structure for NP0054364 (Semecarpetin)