NP-MRD: Showing NP-Card for Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin (NP0047152)

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Record Information

Version

2.0

Created at

2022-03-17 20:35:30 UTC

Updated at

2022-03-17 20:35:30 UTC

NP-MRD ID

NP0047152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin

Description

Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin is found in Areca catechu , Betula spp., Illicium anisatum , Pinus taeda, Salix spp. and Thujopsis dolabrata.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212292D          

 63 71  0  0  0  0            999 V2000
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   -3.5589   -3.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7010   -4.1122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 21  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  6  0  0  0
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 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 19  1  0  0  0  0
 22 23  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
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 33 34  1  0  0  0  0
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 23 38  1  0  0  0  0
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 57 58  1  0  0  0  0
 57 62  1  0  0  0  0
 58 61  1  0  0  0  0
  8 45  1  1  0  0  0
M  END


  Mrv0541 02241212292D          

 63 71  0  0  0  0            999 V2000
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   -3.5589   -3.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589   -4.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1300   -3.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4155   -4.5247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0047152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C45H38O18/c46-18-10-26(53)33-32(11-18)62-43(16-2-5-21(48)24(51)8-16)40(59)37(33)35-27(54)13-28(55)36-38(41(60)44(63-45(35)36)17-3-6-22(49)25(52)9-17)34-29(56)14-31-19(39(34)58)12-30(57)42(61-31)15-1-4-20(47)23(50)7-15/h1-11,13-14,30,37-38,40-44,46-60H,12H2/t30-,37+,38-,40+,41+,42+,43+,44+/m0/s1

> <INCHI_KEY>
PBYRKMXDROOXMU-XKDUFCMJSA-N

> <FORMULA>
C45H38O18

> <MOLECULAR_WEIGHT>
866.7724

> <EXACT_MASS>
866.205814412

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
85.85943859200842

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.436383012

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.059968517303735

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.640182398664432

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1954200537404605

> <JCHEM_POLAR_SURFACE_AREA>
331.14

> <JCHEM_REFRACTIVITY>
219.01630000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arecatannin B1

> <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                                  
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HETATM   21  O   UNK     0      -5.310  -9.986   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.995   1.488   0.000  0.00  0.00           C+0
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HETATM   24  C   UNK     0      -9.328  -0.822   0.000  0.00  0.00           C+0
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HETATM   28  O   UNK     0      -5.327   1.488   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.327  -1.592   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.994  -0.822   0.000  0.00  0.00           C+0
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HETATM   43  C   UNK     0      -1.217 -13.846   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.216 -12.306   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.550 -11.536   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.884 -12.306   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -3.884 -13.846   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.550 -14.616   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -2.550 -16.156   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -5.218 -14.616   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -5.218 -16.156   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -3.884 -16.926   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -3.884 -18.466   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -2.550 -20.776   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -2.550 -19.236   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -5.217 -19.236   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -5.218 -20.776   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.884 -21.546   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       0.117 -11.536   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -6.551 -16.926   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -3.884 -23.086   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      -6.551 -21.546   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -5.218 -11.536   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   45                                                  
CONECT    9    8   10   18                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   12   15   19                                                  
CONECT   17    2                                                            
CONECT   18    9                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21    4                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   38                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   42                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   28   26                                                  
CONECT   28   27   31                                                       
CONECT   29   26   30    1                                                  
CONECT   30   29   31   39                                                  
CONECT   31   28   30   32                                                  
CONECT   32   31   34   35                                                  
CONECT   33   34   37                                                       
CONECT   34   32   33                                                       
CONECT   35   32   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   33   36   40                                                  
CONECT   38   23                                                            
CONECT   39   30                                                            
CONECT   40   37                                                            
CONECT   41   36                                                            
CONECT   42   25                                                            
CONECT   43   44   48                                                       
CONECT   44   43   45   59                                                  
CONECT   45   44   46    8                                                  
CONECT   46   45   47   63                                                  
CONECT   47   46   48   50                                                  
CONECT   48   43   47   49                                                  
CONECT   49   48   52                                                       
CONECT   50   47   51                                                       
CONECT   51   50   52   60                                                  
CONECT   52   49   51   53                                                  
CONECT   53   52   55   56                                                  
CONECT   54   55   58                                                       
CONECT   55   53   54                                                       
CONECT   56   53   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   54   57   61                                                  
CONECT   59   44                                                            
CONECT   60   51                                                            
CONECT   61   58                                                            
CONECT   62   57                                                            
CONECT   63   46                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  142    0
END

View in JSmol

Synonyms

Value	Source
Epicatechin-(4b->8)-epicatechin-(4b->6)-catechin	Generator
Epicatechin-(4β->8)-epicatechin-(4β->6)-catechin	Generator

Chemical Formula

C₄₅H₃₈O₁₈

Average Mass

866.7724 Da

Monoisotopic Mass

866.20581 Da

IUPAC Name

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

arecatannin B1

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C2O

InChI Identifier

InChI=1S/C45H38O18/c46-18-10-26(53)33-32(11-18)62-43(16-2-5-21(48)24(51)8-16)40(59)37(33)35-27(54)13-28(55)36-38(41(60)44(63-45(35)36)17-3-6-22(49)25(52)9-17)34-29(56)14-31-19(39(34)58)12-30(57)42(61-31)15-1-4-20(47)23(50)7-15/h1-11,13-14,30,37-38,40-44,46-60H,12H2/t30-,37+,38-,40+,41+,42+,43+,44+/m0/s1

InChI Key

PBYRKMXDROOXMU-XKDUFCMJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Areca catechu	Plant	KNApSAcK
Betula spp.	Plant	KNApSAcK
Illicium anisatum	Plant	KNApSAcK
Pinus taeda	Plant	KNApSAcK
Salix spp.	Plant	KNApSAcK
Thujopsis dolabrata	Plant	KNApSAcK
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75642 )
proanthocyanidin (CHEBI:75642 )
hydroxyflavan (CHEBI:75642 )

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	3.38	ALOGPS
logP	4.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	331.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	219.02 m³·mol⁻¹	ChemAxon
Polarizability	85.86 Å³	ChemAxon
Number of Rings	9	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

FDB007562

KNApSAcK ID

C00009089

Chemspider ID

Not Available

KEGG Compound ID

C17892

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arecatannin_B1

METLIN ID

Not Available

PubChem Compound

14237657

PDB ID

Not Available

ChEBI ID

75642

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin (NP0047152)

MOL for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D MOL for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D SDF for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D-SDF for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

PDB for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D PDB for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

SMILES for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

INCHI for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

Structure for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D Structure for NP0047152 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)