NP-MRD: Showing NP-Card for (5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one (NP0145761)

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Record Information

Version

2.0

Created at

2022-09-02 01:01:34 UTC

Updated at

2022-09-02 01:01:34 UTC

NP-MRD ID

NP0145761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one

Description

(5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]Trideca-1,3(7),8-trien-10-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one is found in Ochna afzelii. Based on a literature review very few articles have been published on (5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]Trideca-1,3(7),8-trien-10-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203012D          

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M  END

     RDKit          3D

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  Mrv1652309022203012D          

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  5  6  2  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 30 38  1  0  0  0  0
 11 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>
NP0145761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@H]1OC2=CC3=C(C(=O)C[C@H](O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]1C(=O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H24O9/c1-38-19-9-4-16(5-10-19)31-28(29(36)20-11-8-18(33)12-21(20)34)27-25(40-31)14-24-26(30(27)37)22(35)13-23(39-24)15-2-6-17(32)7-3-15/h2-12,14,23,28,31-34,37H,13H2,1H3/t23-,28+,31+/m0/s1

> <INCHI_KEY>
YBNWSGJTIRDUAL-GFDPGFINSA-N

> <FORMULA>
C31H24O9

> <MOLECULAR_WEIGHT>
540.524

> <EXACT_MASS>
540.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
55.76254567446737

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.823219913333332

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.457085040985934

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.673906690839645

> <JCHEM_PKA_STRONGEST_BASIC>
-4.57380868420061

> <JCHEM_POLAR_SURFACE_AREA>
142.74999999999997

> <JCHEM_REFRACTIVITY>
143.69249999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.437  -4.947   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.667  -3.613   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.127  -3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.357  -2.279   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.817  -2.279   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.047  -3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.197  -0.533   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.077  -0.902   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.584  -0.582   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.047   0.242   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.459  -0.078   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.490   1.066   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.014   2.531   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.044   3.675   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.492   2.851   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.523   1.707   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.029   2.027   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.864  -0.533   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.199  -5.153   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.199  -6.693   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.533  -7.463   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.865  -7.463   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.531  -6.693   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.817  -4.947   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.357  -4.947   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   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15    7   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25                                                            
CONECT   27   12   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   30   11                                                       
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

C₃₁H₂₄O₉

Average Mass

540.5240 Da

Monoisotopic Mass

540.14203 Da

IUPAC Name

(5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

Traditional Name

(5S,6S,12S)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@H]1OC2=CC3=C(C(=O)C[C@H](O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]1C(=O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C31H24O9/c1-38-19-9-4-16(5-10-19)31-28(29(36)20-11-8-18(33)12-21(20)34)27-25(40-31)14-24-26(30(27)37)22(35)13-23(39-24)15-2-6-17(32)7-3-15/h2-12,14,23,28,31-34,37H,13H2,1H3/t23-,28+,31+/m0/s1

InChI Key

YBNWSGJTIRDUAL-GFDPGFINSA-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
Ochna afzelii	LOTUS Database	35616633

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
Furanoflavonoid or dihydroflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Neolignan skeleton
Hydroxyflavonoid
Flavanone
Flavan
Furanochromone
Alkyl-phenylketone
Chromone
Benzopyran
Chromane
1-benzopyran
Coumaran
Phenylketone
Benzofuran
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	4.86	ALOGPS
logP	5.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.69 m³·mol⁻¹	ChemAxon
Polarizability	55.76 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

556964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

641712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one (NP0145761)

MOL for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

3D MOL for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

3D SDF for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

3D-SDF for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

PDB for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

3D PDB for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

SMILES for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

INCHI for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

Structure for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)

3D Structure for NP0145761 ((5s,6s,12s)-6-(2,4-dihydroxybenzoyl)-8-hydroxy-12-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-10-one)