NP-MRD: Showing NP-Card for 3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione (NP0331011)

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Record Information

Version

1.0

Created at

2022-09-12 16:55:39 UTC

Updated at

2022-09-12 16:55:39 UTC

NP-MRD ID

NP0331011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione

Description

3,19-Dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]Henicosa-2,4(9),10-triene-5,13-dione belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. 3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione is found in Cryptocarya obovata. 3,19-Dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]Henicosa-2,4(9),10-triene-5,13-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514022D          

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M  END

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M  END


  Mrv1533004191514022D          

 39 44  0  0  0  0            999 V2000
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   11.8709    3.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8838    2.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1758    2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 15 21  2  0  0  0  0
 17 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
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  4 31  1  0  0  0  0
 32 29  1  4  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
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C3CC(CCCC(=O)OC2=CC2=C1C(=O)CC(O2)C1=CC=CC=C1)OC(O)(C3)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O7/c33-24-17-25(21-10-5-2-6-11-21)37-27-18-26-29(31(35)30(24)27)22-16-23(12-7-13-28(34)38-26)39-32(36,19-22)15-14-20-8-3-1-4-9-20/h1-6,8-11,14-15,18,22-23,25,35-36H,7,12-13,16-17,19H2

> <INCHI_KEY>
QEBDFZMXMJQISE-UHFFFAOYSA-N

> <FORMULA>
C32H30O7

> <MOLECULAR_WEIGHT>
526.585

> <EXACT_MASS>
526.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.123529635703974

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2,4(9),10-triene-5,13-dione

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
6.179101539666666

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.645157162089145

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.724749469682571

> <JCHEM_PKA_STRONGEST_BASIC>
-4.266385087805642

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
145.54609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2,4(9),10-triene-5,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      12.864   2.807   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.360   1.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.368   0.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.881   0.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.889  -0.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.401  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.409  -1.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.905  -3.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.393  -3.304   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.385  -2.140   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.937  -0.667   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      13.873  -2.431   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.864  -1.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.352  -1.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.344  -0.394   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.832  -0.685   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.824   0.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.328   1.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.840   2.225   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.344   3.680   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.848   1.061   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.311   0.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.807  -1.267   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.295  -1.558   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.287  -0.394   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.791   1.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.303   1.352   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.905   1.061   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.897   2.225   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.348   3.664   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.385   1.934   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.219   3.016   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.195   4.556   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.516   5.346   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.492   6.886   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.814   7.677   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.159   6.928   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.183   5.388   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.862   4.597   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   15                                                  
CONECT   22   17   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28    6   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29    4                                                       
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₇

Average Mass

526.5850 Da

Monoisotopic Mass

526.19915 Da

IUPAC Name

3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2,4(9),10-triene-5,13-dione

Traditional Name

3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2,4(9),10-triene-5,13-dione

CAS Registry Number

Not Available

SMILES

OC1=C2C3CC(CCCC(=O)OC2=CC2=C1C(=O)CC(O2)C1=CC=CC=C1)OC(O)(C3)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C32H30O7/c33-24-17-25(21-10-5-2-6-11-21)37-27-18-26-29(31(35)30(24)27)22-16-23(12-7-13-28(34)38-26)39-32(36,19-22)15-14-20-8-3-1-4-9-20/h1-6,8-11,14-15,18,22-23,25,35-36H,7,12-13,16-17,19H2

InChI Key

QEBDFZMXMJQISE-UHFFFAOYSA-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
Cryptocarya obovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Styrene
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Lactone
Ketone
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	4.22	ALOGPS
logP	6.18	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	145.55 m³·mol⁻¹	ChemAxon
Polarizability	57.12 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

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

73809326

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione (NP0331011)

MOL for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

3D MOL for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

3D SDF for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

3D-SDF for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

PDB for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

3D PDB for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

SMILES for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

INCHI for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

Structure for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)

3D Structure for NP0331011 (3,19-dihydroxy-7-phenyl-19-(2-phenylethenyl)-8,12,18-trioxatetracyclo[15.3.1.0²,¹¹.0⁴,⁹]henicosa-2(11),3,9-triene-5,13-dione)