NP-MRD: Showing NP-Card for ent-Epiafzeiechin-(4alpha->8)-epiafzelechin (NP0056277)

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Record Information

Version

2.0

Created at

2022-04-28 02:05:57 UTC

Updated at

2022-04-28 02:05:57 UTC

NP-MRD ID

NP0056277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-Epiafzeiechin-(4alpha->8)-epiafzelechin

Description

(2S,2'S,3S,3'S,4S)-3,3',4,4'-Tetrahydro-2beta,2'beta-bis(4-hydroxyphenyl)-4alpha,8'-bi[2H-1-benzopyran]-3beta,3'beta,5,5',7,7'-hexol 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''. ent-Epiafzeiechin-(4alpha->8)-epiafzelechin is found in Cassia fistula and Cassia javanica . Based on a literature review very few articles have been published on (2S,2'S,3S,3'S,4S)-3,3',4,4'-Tetrahydro-2beta,2'beta-bis(4-hydroxyphenyl)-4alpha,8'-bi[2H-1-benzopyran]-3beta,3'beta,5,5',7,7'-hexol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204052D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282204052D          

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  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
  4 14  1  6  0  0  0
  3 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 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  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 29  1  6  0  0  0
 17 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
 30 34  1  0  0  0  0
  2 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
  1 38  1  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C=C3)=C2O[C@H]1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O10/c31-15-5-1-13(2-6-15)28-22(37)11-18-19(34)12-21(36)25(30(18)40-28)26-24-20(35)9-17(33)10-23(24)39-29(27(26)38)14-3-7-16(32)8-4-14/h1-10,12,22,26-29,31-38H,11H2/t22-,26-,27-,28-,29-/m0/s1

> <INCHI_KEY>
JESPWQGCCOLVKQ-WQJHFXEDSA-N

> <FORMULA>
C30H26O10

> <MOLECULAR_WEIGHT>
546.528

> <EXACT_MASS>
546.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
54.38957555285564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.7228756570000003

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.261914644210217

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.834418872680184

> <JCHEM_PKA_STRONGEST_BASIC>
-3.284978724578348

> <JCHEM_POLAR_SURFACE_AREA>
180.29999999999998

> <JCHEM_REFRACTIVITY>
142.5462

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S)-2-(4-hydroxyphenyl)-4-[(2S,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <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      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.573  -3.374   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    4                                                            
CONECT   15    3   16   32                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29   19                                                            
CONECT   30   17   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   15   33                                                  
CONECT   33   32                                                            
CONECT   34   30                                                            
CONECT   35    2   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37    1                                                       
CONECT   39   37                                                            
CONECT   40   35                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(2S,2's,3S,3's,4S)-3,3',4,4'-Tetrahydro-2b,2'b-bis(4-hydroxyphenyl)-4a,8'-bi[2H-1-benzopyran]-3b,3'b,5,5',7,7'-hexol	Generator
(2S,2's,3S,3's,4S)-3,3',4,4'-Tetrahydro-2β,2'β-bis(4-hydroxyphenyl)-4α,8'-bi[2H-1-benzopyran]-3β,3'β,5,5',7,7'-hexol	Generator

Chemical Formula

C₃₀H₂₆O₁₀

Average Mass

546.5280 Da

Monoisotopic Mass

546.15260 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C=C3)=C2O[C@H]1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H26O10/c31-15-5-1-13(2-6-15)28-22(37)11-18-19(34)12-21(36)25(30(18)40-28)26-24-20(35)9-17(33)10-23(24)39-29(27(26)38)14-3-7-16(32)8-4-14/h1-10,12,22,26-29,31-38H,11H2/t22-,26-,27-,28-,29-/m0/s1

InChI Key

JESPWQGCCOLVKQ-WQJHFXEDSA-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
Cassia fistula	Plant	KNApSAcK
Cassia javanica	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

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan-3-ol
Flavan
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
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	2.56	ALOGPS
logP	3.72	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	180.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.55 m³·mol⁻¹	ChemAxon
Polarizability	54.39 Å³	ChemAxon
Number of Rings	6	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

14015944

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ent-Epiafzeiechin-(4alpha->8)-epiafzelechin (NP0056277)

MOL for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

3D MOL for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

3D SDF for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

3D-SDF for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

PDB for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

3D PDB for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

SMILES for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

INCHI for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

Structure for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)

3D Structure for NP0056277 (ent-Epiafzeiechin-(4alpha->8)-epiafzelechin)