NP-MRD: Showing NP-Card for 7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol (NP0265934)

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Record Information

Version

2.0

Created at

2022-09-08 10:06:10 UTC

Updated at

2022-09-08 10:06:10 UTC

NP-MRD ID

NP0265934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol

Description

2-Methyl-6-(methylthio)pyrazine belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. 7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol is found in Aesculus hippocastanum and Parameria laevigata. 2-Methyl-6-(methylthio)pyrazine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209352D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241209352D          

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   -1.2641   -1.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305   -1.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075   -2.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973   -3.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973   -3.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5637   -4.2536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2 30  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 33  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 20  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  2  0  0  0  0
 12 39  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 41  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 32  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 34  2  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  0  0  0  0
 26 27  1  0  0  0  0
 26 35  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 38  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O)C3=C(OC4(OC5=C(C3C4O)C(O)=CC(O)=C5)C3=CC=C(O)C(O)=C3)C=C2OC1C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2

> <INCHI_KEY>
BEPYKTSNKZMROV-UHFFFAOYSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.5044

> <EXACT_MASS>
576.126776232

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
56.64019584249761

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2(11),3,9,15(20),16,18-hexaene-3,6,17,19,21-pentol

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.590532096666666

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111216654632905

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.666792986478557

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8766022958579898

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
144.19629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2(11),3,9,15(20),16,18-hexaene-3,6,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.361   7.368   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.074   8.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.787   7.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.787   5.793   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.217   4.936   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.361   5.793   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.792   5.078   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.790   5.078   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.220   5.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.078   3.934   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.652   4.221   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.646  -5.937   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.646  -7.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.076  -8.083   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.076  -9.657   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.357   4.936   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.508   1.359   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.507   2.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.075   2.360   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.074   3.648   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.643   3.361   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.500   1.787   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.931   0.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.073  -0.500   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.360  -1.358   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.648  -0.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.935  -1.216   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.078  -2.789   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.366  -3.361   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.074   9.657   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.931   2.360   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.787   3.648   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.217   3.505   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.360   1.787   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.504   0.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.935   1.645   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.360  -2.933   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.790  -3.648   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.934  -5.078   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.222  -5.793   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.222  -7.368   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.652  -7.940   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   33                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9   20                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10                                                            
CONECT   12   13   39                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14                                                            
CONECT   16    4   21                                                       
CONECT   17   18                                                            
CONECT   18   10   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20    8   19   21                                                  
CONECT   21   16   20   22   32                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   38                                                  
CONECT   29   28                                                            
CONECT   30    2                                                            
CONECT   31   32                                                            
CONECT   32   21   31   33                                                  
CONECT   33    5   32   34                                                  
CONECT   34   23   33   35                                                  
CONECT   35   26   34   36                                                  
CONECT   36   35                                                            
CONECT   37   25   38                                                       
CONECT   38   28   37   39                                                  
CONECT   39   12   38   40                                                  
CONECT   40   39   41                                                       
CONECT   41   14   40   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Epicatechin-(2b->7,4b->6)-catechin	HMDB, Generator
Epicatechin-(2β->7,4β->6)-catechin	Generator

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5044 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2(11),3,9,15(20),16,18-hexaene-3,6,17,19,21-pentol

Traditional Name

7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2(11),3,9,15(20),16,18-hexaene-3,6,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

OC1CC2=C(O)C3=C(OC4(OC5=C(C3C4O)C(O)=CC(O)=C5)C3=CC=C(O)C(O)=C3)C=C2OC1C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2

InChI Key

BEPYKTSNKZMROV-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
Aesculus hippocastanum	LOTUS Database	35616633
Parameria laevigata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
Alkylarylthioether
Pyrazine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.46	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	56.64 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

HMDB0040061

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019748

KNApSAcK ID

Not Available

Chemspider ID

453932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol (NP0265934)

MOL for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

3D MOL for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

3D SDF for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

3D-SDF for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

PDB for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

3D PDB for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

SMILES for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

INCHI for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

Structure for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)

3D Structure for NP0265934 (7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol)