NP-MRD: Showing NP-Card for Robinetinidol-(2beta->7,4beta->8)-catechin (NP0056438)

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Record Information

Version

2.0

Created at

2022-04-28 02:13:21 UTC

Updated at

2022-04-28 02:13:21 UTC

NP-MRD ID

NP0056438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Robinetinidol-(2beta->7,4beta->8)-catechin

Description

(1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Robinetinidol-(2beta->7,4beta->8)-catechin is found in Acacia mearnsii . Based on a literature review very few articles have been published on (1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204132D          

 42 48  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282204132D          

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    3.7532    5.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936    6.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993    8.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618    7.8849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9831    2.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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
  1  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  5  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  1  0  0  0
 19 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
 15 31  1  0  0  0  0
  9 32  1  1  0  0  0
  8 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 35 41  1  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@H]1C1=CC(O)=C(O)C=C1)C1=C(O[C@@]3(OC4=C(C=CC(O)=C4)[C@H]1[C@@H]3O)C1=CC(O)=C(O)C(O)=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-13-2-3-14-22(8-13)41-30(12-6-19(35)26(38)20(36)7-12)29(39)24(14)25-23(42-30)10-17(33)15-9-21(37)27(40-28(15)25)11-1-4-16(32)18(34)5-11/h1-8,10,21,24,27,29,31-39H,9H2/t21-,24+,27-,29-,30-/m0/s1

> <INCHI_KEY>
HFHKGXMFMWRZHD-RCSLUZJGSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.51

> <EXACT_MASS>
576.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
56.74125115020479

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
3.590532096666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.05290401091958

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.524326408706896

> <JCHEM_PKA_STRONGEST_BASIC>
-3.862893346806758

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
144.19630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.430   6.377   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.817   4.886   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.720   3.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.236   4.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.849   5.706   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.946   6.787   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.958   8.327   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.877   9.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.556   7.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.309   5.718   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.228   6.816   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.240   8.356   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.337   9.436   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.912   9.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.427   8.376   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.439   6.836   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.889   6.056   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.877   4.516   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.463   3.756   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.791   4.537   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.779   6.077   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.130   3.777   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.475   2.216   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.853   1.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.841  -0.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.499  -0.864   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.826  -0.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.814   1.457   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.511  -2.403   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.169  -0.884   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.755   9.157   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.351   6.056   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.478  10.842   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.550  12.071   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.150  13.489   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.678  13.679   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.606  12.450   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.006  11.032   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.135  12.639   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.279  15.097   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.222  14.718   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.302   4.476   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13   33                                             
CONECT    9    8   10   32                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31   15                                                            
CONECT   32    9                                                            
CONECT   33    8   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37   33                                                       
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   35                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5100 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

(1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol

Traditional Name

(1R,5S,6S,13S,21S)-5-(3,4-dihydroxyphenyl)-13-(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,21-tetrol

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O[C@H]1C1=CC(O)=C(O)C=C1)C1=C(O[C@@]3(OC4=C(C=CC(O)=C4)[C@H]1[C@@H]3O)C1=CC(O)=C(O)C(O)=C1)C=C2O

InChI Identifier

InChI=1S/C30H24O12/c31-13-2-3-14-22(8-13)41-30(12-6-19(35)26(38)20(36)7-12)29(39)24(14)25-23(42-30)10-17(33)15-9-21(37)27(40-28(15)25)11-1-4-16(32)18(34)5-11/h1-8,10,21,24,27,29,31-39H,9H2/t21-,24+,27-,29-,30-/m0/s1

InChI Key

HFHKGXMFMWRZHD-RCSLUZJGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acacia mearnsii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

A-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Epigallocatechin
Catechin
Pyranoflavonoid
Hydroxyflavonoid
Flavan-3-ol
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Pyranochromene
1-benzopyran
Benzopyran
Chromane
Pyrogallol derivative
Benzenetriol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
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
logP	2.48	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.52	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	56.74 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

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

163184546

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Robinetinidol-(2beta->7,4beta->8)-catechin (NP0056438)

MOL for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

3D MOL for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

3D SDF for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

3D-SDF for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

PDB for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

3D PDB for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

SMILES for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

INCHI for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

Structure for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)

3D Structure for NP0056438 (Robinetinidol-(2beta->7,4beta->8)-catechin)