NP-MRD: Showing NP-Card for 2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol (NP0250901)

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Record Information

Version

2.0

Created at

2022-09-07 13:53:58 UTC

Updated at

2022-09-07 13:53:58 UTC

NP-MRD ID

NP0250901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

Description

2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol is found in Morus mongolica. Based on a literature review very few articles have been published on 2-[(1R,9S,12S)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]Trideca-2(7),3,5,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215532D          

 43 49  0  0  1  0            999 V2000
    3.3021    0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072215532D          

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    4.2933    5.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    3.0231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4461    1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0550    2.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3128    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537    1.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    1.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    1.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  6  8  1  0  0  0  0
  8  9  2  0  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  2  0  0  0  0
 13 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
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  6  0  0  0
  2 35  1  0  0  0  0
 34 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
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
 42 43  1  0  0  0  0
  2 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@H]([C@H](C(=O)C3=CC=C(O)C=C3O)C(=C1)C1=C(O)C=C(C=C1O)C1=CC3=CC=C(O)C=C3O1)C1=CC=C(O)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C34H26O9/c1-34-14-23(21-6-4-20(37)13-30(21)43-34)31(33(41)22-7-5-18(35)11-25(22)38)24(15-34)32-26(39)8-17(9-27(32)40)28-10-16-2-3-19(36)12-29(16)42-28/h2-13,15,23,31,35-40H,14H2,1H3/t23-,31-,34-/m0/s1

> <INCHI_KEY>
KINVGWHLWGHQKZ-UENJDZAYSA-N

> <FORMULA>
C34H26O9

> <MOLECULAR_WEIGHT>
578.573

> <EXACT_MASS>
578.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
60.53689506317062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,9S,12S)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

> <JCHEM_LOGP>
6.184824903

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.516338465851058

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.747364372159151

> <JCHEM_PKA_STRONGEST_BASIC>
-2.865880795714902

> <JCHEM_POLAR_SURFACE_AREA>
160.82

> <JCHEM_REFRACTIVITY>
157.89599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,9S,12S)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.164   0.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.678   1.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.842   2.832   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.953   4.368   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.414   4.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.724   6.363   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.573   7.385   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.185   6.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.337   5.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.798   6.312   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.050   5.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.290   6.328   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.798   6.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.821   7.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.335   8.631   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.358   9.783   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.827   8.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.804   7.790   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.264   7.779   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.027   4.317   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.565   3.831   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.256   2.323   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.945   5.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.635   6.909   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.464   8.207   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.787   8.195   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.250   8.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.402   9.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.092  10.767   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.245  12.053   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.629  10.858   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.477   9.572   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.014   9.663   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.409   5.643   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.566   3.575   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.244   4.635   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.969   5.499   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.584   4.826   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.473   3.290   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.912   2.618   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.749   2.427   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.134   3.099   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.142   1.935   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35   43                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   10                                                       
CONECT   20    9   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
CONECT   23    4   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32                                                            
CONECT   34   23   35   36                                                  
CONECT   35   34    2                                                       
CONECT   36   34   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36   43                                                  
CONECT   43   42    2                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₂₆O₉

Average Mass

578.5730 Da

Monoisotopic Mass

578.15768 Da

IUPAC Name

2-[(1R,9S,12S)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

Traditional Name

2-[(1R,9S,12S)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@H]([C@H](C(=O)C3=CC=C(O)C=C3O)C(=C1)C1=C(O)C=C(C=C1O)C1=CC3=CC=C(O)C=C3O1)C1=CC=C(O)C=C1O2

InChI Identifier

InChI=1S/C34H26O9/c1-34-14-23(21-6-4-20(37)13-30(21)43-34)31(33(41)22-7-5-18(35)11-25(22)38)24(15-34)32-26(39)8-17(9-27(32)40)28-10-16-2-3-19(36)12-29(16)42-28/h2-13,15,23,31,35-40H,14H2,1H3/t23-,31-,34-/m0/s1

InChI Key

KINVGWHLWGHQKZ-UENJDZAYSA-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
Morus mongolica	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	6.18	ChemAxon
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	157.9 m³·mol⁻¹	ChemAxon
Polarizability	60.54 Å³	ChemAxon
Number of Rings	7	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

9874555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11699830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol (NP0250901)

MOL for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

3D MOL for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

3D SDF for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

3D-SDF for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

PDB for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

3D PDB for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

SMILES for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

INCHI for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

Structure for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)

3D Structure for NP0250901 (2-[(1r,9s,12s)-12-(2,4-dihydroxybenzoyl)-5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol)