NP-MRD: Showing NP-Card for Lophirone C (NP0054394)

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Record Information

Version

2.0

Created at

2022-04-28 00:45:30 UTC

Updated at

2022-04-28 00:45:30 UTC

NP-MRD ID

NP0054394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lophirone C

Description

(E)-3-[[3beta-(2,4-Dihydroxybenzoyl)-2,3-dihydro-2alpha-(4-hydroxyphenyl)benzofuran]-5-yl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Lophirone C is found in Lophira alata , Lophira lanceolata , Ochna afzelii and Ochna integerrima . Based on a literature review very few articles have been published on (E)-3-[[3beta-(2,4-Dihydroxybenzoyl)-2,3-dihydro-2alpha-(4-hydroxyphenyl)benzofuran]-5-yl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202452D          

 38 42  0  0  1  0            999 V2000
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282202452D          

 38 42  0  0  1  0            999 V2000
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 34 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1OC2=C(C=C(\C=C\C(=O)C3=CC=C(O)C=C3O)C=C2)[C@@H]1C(=O)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O8/c31-18-5-3-17(4-6-18)30-28(29(37)22-10-8-20(33)15-26(22)36)23-13-16(2-12-27(23)38-30)1-11-24(34)21-9-7-19(32)14-25(21)35/h1-15,28,30-33,35-36H/b11-1+/t28-,30-/m1/s1

> <INCHI_KEY>
ZHASXSWRTDVPQX-QBIWMMAFSA-N

> <FORMULA>
C30H22O8

> <MOLECULAR_WEIGHT>
510.498

> <EXACT_MASS>
510.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.694835263484585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-[(2S,3S)-3-(2,4-dihydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
6.471847151

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.847769607248823

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.037829871384343

> <JCHEM_PKA_STRONGEST_BASIC>
-4.896022021463263

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
140.74009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(2S,3S)-3-(2,4-dihydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-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       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.743   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.340   3.801   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.401   6.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.432   7.234   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.938   6.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.414   5.449   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.383   4.305   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.968   8.058   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.895   6.410   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.455   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.123   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.456   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.456  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.123  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.789  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      16.790  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17    7   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22                                                            
CONECT   26   20                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36                                                            
CONECT   38   34                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(e)-3-[[3b-(2,4-Dihydroxybenzoyl)-2,3-dihydro-2a-(4-hydroxyphenyl)benzofuran]-5-yl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one	Generator
(e)-3-[[3Β-(2,4-dihydroxybenzoyl)-2,3-dihydro-2α-(4-hydroxyphenyl)benzofuran]-5-yl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one	Generator

Chemical Formula

C₃₀H₂₂O₈

Average Mass

510.4980 Da

Monoisotopic Mass

510.13147 Da

IUPAC Name

(2E)-3-[(2S,3S)-3-(2,4-dihydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-3-[(2S,3S)-3-(2,4-dihydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1OC2=C(C=C(\C=C\C(=O)C3=CC=C(O)C=C3O)C=C2)[C@@H]1C(=O)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O8/c31-18-5-3-17(4-6-18)30-28(29(37)22-10-8-20(33)15-26(22)36)23-13-16(2-12-27(23)38-30)1-11-24(34)21-9-7-19(32)14-25(21)35/h1-15,28,30-33,35-36H/b11-1+/t28-,30-/m1/s1

InChI Key

ZHASXSWRTDVPQX-QBIWMMAFSA-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
Lophira alata	Plant	KNApSAcK
Lophira lanceolata	Plant	KNApSAcK
Ochna afzelii	Plant	KNApSAcK
Ochna integerrima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Furanochalcone
Neolignan skeleton
2'-hydroxychalcone
Alkyl-phenylketone
Benzofuran
Coumaran
Phenylketone
Benzoyl
Aryl alkyl ketone
Aryl ketone
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	4.94	ALOGPS
logP	6.47	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.04	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.74 m³·mol⁻¹	ChemAxon
Polarizability	52.69 Å³	ChemAxon
Number of Rings	5	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

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

12085730

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lophirone C (NP0054394)

MOL for NP0054394 (Lophirone C)

3D MOL for NP0054394 (Lophirone C)

3D SDF for NP0054394 (Lophirone C)

3D-SDF for NP0054394 (Lophirone C)

PDB for NP0054394 (Lophirone C)

3D PDB for NP0054394 (Lophirone C)

SMILES for NP0054394 (Lophirone C)

INCHI for NP0054394 (Lophirone C)

Structure for NP0054394 (Lophirone C)

3D Structure for NP0054394 (Lophirone C)