NP-MRD: Showing NP-Card for 2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol (NP0303912)

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Record Information

Version

2.0

Created at

2022-09-10 18:39:07 UTC

Updated at

2022-09-10 18:39:08 UTC

NP-MRD ID

NP0303912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol

Description

2-{[(5S,6R,11S,12R)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]Trideca-1,3(7),8-trien-5-yl]methyl}benzene-1,3,5-triol belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. 2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol is found in Sanguisorba officinalis. Based on a literature review very few articles have been published on 2-{[(5S,6R,11S,12R)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]Trideca-1,3(7),8-trien-5-yl]methyl}benzene-1,3,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220392D          

 41 46  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309102220392D          

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    5.6424   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -3.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -4.0789    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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  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  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 18 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 29 38  1  0  0  0  0
 12 38  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
  2 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C1O[C@@H](CC3=C(O)C=C(O)C=C3O)[C@@H](C1=C2O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O11/c31-14-7-19(34)15(20(35)8-14)10-25-27(12-1-3-17(32)21(36)5-12)28-26(40-25)11-24-16(29(28)39)9-23(38)30(41-24)13-2-4-18(33)22(37)6-13/h1-8,11,23,25,27,30-39H,9-10H2/t23-,25-,27-,30+/m0/s1

> <INCHI_KEY>
FFCVTFZKQFEUKL-BKVCSMAQSA-N

> <FORMULA>
C30H26O11

> <MOLECULAR_WEIGHT>
562.527

> <EXACT_MASS>
562.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
56.87479542609543

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(5S,6R,11S,12R)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol

> <JCHEM_LOGP>
4.034741160666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.18604201936915

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.742811317224247

> <JCHEM_PKA_STRONGEST_BASIC>
-5.270449784131515

> <JCHEM_POLAR_SURFACE_AREA>
200.52999999999997

> <JCHEM_REFRACTIVITY>
145.3005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(5S,6R,11S,12R)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -7.127  -8.948   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.357  -7.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.127  -6.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.357  -4.947   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.127  -3.613   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.817  -4.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.047  -3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.197  -0.533   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.077  -0.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.584  -0.582   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.060   0.882   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.029   2.027   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.505   3.492   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.523   1.707   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.492   2.851   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.047   0.242   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.531  -2.073   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.199  -5.153   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.199  -6.693   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.533  -7.463   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.865  -7.463   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.865  -9.003   0.000  0.00  0.00           O+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      -4.047  -6.280   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.507  -6.280   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.817  -7.614   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   38                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16    8   18                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   13   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   38                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
CONECT   38   29   12                                                       
CONECT   39    6   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39    2                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₁

Average Mass

562.5270 Da

Monoisotopic Mass

562.14751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C1O[C@@H](CC3=C(O)C=C(O)C=C3O)[C@@H](C1=C2O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H26O11/c31-14-7-19(34)15(20(35)8-14)10-25-27(12-1-3-17(32)21(36)5-12)28-26(40-25)11-24-16(29(28)39)9-23(38)30(41-24)13-2-4-18(33)22(37)6-13/h1-8,11,23,25,27,30-39H,9-10H2/t23-,25-,27-,30+/m0/s1

InChI Key

FFCVTFZKQFEUKL-BKVCSMAQSA-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
Sanguisorba officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Furanoflavonoid or dihydroflavonoid
Linear 1,7-diphenylheptane skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
1-phenylcoumaran
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzenetriol
Phloroglucinol derivative
Catechol
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
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

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

10290183

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21676381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol (NP0303912)

MOL for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

3D MOL for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

3D SDF for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

3D-SDF for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

PDB for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

3D PDB for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

SMILES for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

INCHI for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

Structure for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)

3D Structure for NP0303912 (2-{[(5s,6r,11s,12r)-6,12-bis(3,4-dihydroxyphenyl)-8,11-dihydroxy-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,7-trien-5-yl]methyl}benzene-1,3,5-triol)