NP-MRD: Showing NP-Card for 8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol (NP0056057)

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Record Information

Version

2.0

Created at

2022-04-28 01:56:38 UTC

Updated at

2022-04-28 01:56:39 UTC

NP-MRD ID

NP0056057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol

Description

8-Trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Thus, 8-trans-[2-(6-benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol is considered to be a flavonoid. 8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol is found in Dracaena draco . Based on a literature review very few articles have been published on 8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203562D          

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  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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 13 25  1  0  0  0  0
 12 26  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 30 33  1  6  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
  1 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CC[C@H](OC2=C(\C=C\C2=C(OC)C(C)=C(O)C=C2OC(=O)C2=CC=CC=C2)C(O)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O7/c1-20-26(34)18-30(40-33(36)22-12-8-5-9-13-22)25(31(20)38-3)15-14-23-27(35)19-29(37-2)24-16-17-28(39-32(23)24)21-10-6-4-7-11-21/h4-15,18-19,28,34-35H,16-17H2,1-3H3/b15-14+/t28-/m0/s1

> <INCHI_KEY>
YKHFNHVQGRPOOZ-ZJYVBTJHSA-N

> <FORMULA>
C33H30O7

> <MOLECULAR_WEIGHT>
538.596

> <EXACT_MASS>
538.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.48833170788947

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-[(E)-2-[(2S)-7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]ethenyl]-3-methoxy-4-methylphenyl benzoate

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
7.676496571666665

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.814843296554988

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.99545246130633

> <JCHEM_PKA_STRONGEST_BASIC>
-4.392208968562638

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
153.90169999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-[(E)-2-[(2S)-7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]ethenyl]-3-methoxy-4-methylphenyl benzoate

> <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      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   13                                                            
CONECT   26   12                                                            
CONECT   27   11   28                                                       
CONECT   28   27                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31    2                                                       
CONECT   33   30   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39    1   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₇

Average Mass

538.5960 Da

Monoisotopic Mass

538.19915 Da

IUPAC Name

5-hydroxy-2-[(E)-2-[(2S)-7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]ethenyl]-3-methoxy-4-methylphenyl benzoate

Traditional Name

5-hydroxy-2-[(E)-2-[(2S)-7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]ethenyl]-3-methoxy-4-methylphenyl benzoate

CAS Registry Number

Not Available

SMILES

COC1=C2CC[C@H](OC2=C(\C=C\C2=C(OC)C(C)=C(O)C=C2OC(=O)C2=CC=CC=C2)C(O)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H30O7/c1-20-26(34)18-30(40-33(36)22-12-8-5-9-13-22)25(31(20)38-3)15-14-23-27(35)19-29(37-2)24-16-17-28(39-32(23)24)21-10-6-4-7-11-21/h4-15,18-19,28,34-35H,16-17H2,1-3H3/b15-14+/t28-/m0/s1

InChI Key

YKHFNHVQGRPOOZ-ZJYVBTJHSA-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
Dracaena draco	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Stilbene
Benzopyran
Methoxyphenol
Benzoate ester
1-benzopyran
Chromane
Phenol ester
Benzoic acid or derivatives
Benzoyl
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020254 )

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	5.87	ALOGPS
logP	7.68	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	153.9 m³·mol⁻¹	ChemAxon
Polarizability	57.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008791

Chemspider ID

24842650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol (NP0056057)

MOL for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

3D MOL for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

3D SDF for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

3D-SDF for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

PDB for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

3D PDB for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

SMILES for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

INCHI for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

Structure for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)

3D Structure for NP0056057 (8-trans-[2-(6-Benzoyloxy-4-hydroxy-2-methoxy-3-methylphenyl)ethenyl]-5-methoxyflavan-7-ol)