NP-MRD: Showing NP-Card for (+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone (NP0074598)

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Record Information

Version

2.0

Created at

2022-04-28 19:53:46 UTC

Updated at

2022-04-28 19:53:46 UTC

NP-MRD ID

NP0074598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone

Description

(2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. (+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone is found in Duranta erecta and Duranta repens. Based on a literature review very few articles have been published on (2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221532D          

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M  END

     RDKit          3D

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 15 16  1  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  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 11 27  1  0  0  0  0
  5 28  1  0  0  0  0
  2 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
  1 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC(=C(O)C(=O)C2=C1OC)C1=CC=C(O)C(CCCCCC[C@H](C)COC(C)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O9/c1-16(15-36-17(2)29)9-7-5-6-8-10-18-13-19(11-12-20(18)30)26-25(33)24(32)23-22(37-26)14-21(31)27(34-3)28(23)35-4/h11-14,16,30-31,33H,5-10,15H2,1-4H3/t16-/m0/s1

> <INCHI_KEY>
PEZYILOZNWLRTK-INIZCTEOSA-N

> <FORMULA>
C28H34O9

> <MOLECULAR_WEIGHT>
514.571

> <EXACT_MASS>
514.220282675

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.58830933184945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.7929092403333335

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.722972780510087

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.898650930113732

> <JCHEM_PKA_STRONGEST_BASIC>
-3.817986318044471

> <JCHEM_POLAR_SURFACE_AREA>
131.75

> <JCHEM_REFRACTIVITY>
138.62679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate

> <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     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.669 -13.860   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -11.550   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  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2    7   32                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   28                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   11                                                            
CONECT   28    5                                                            
CONECT   29    2   30   36                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31    1                                                       
CONECT   33   31                                                            
CONECT   34   30   35                                                       
CONECT   35   34                                                            
CONECT   36   29   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2S)-8-[5-(3,7-Dihydroxy-5,6-dimethoxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₉

Average Mass

514.5710 Da

Monoisotopic Mass

514.22028 Da

IUPAC Name

(2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate

Traditional Name

(2S)-8-[5-(3,7-dihydroxy-5,6-dimethoxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-2-methyloctyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC(=C(O)C(=O)C2=C1OC)C1=CC=C(O)C(CCCCCC[C@H](C)COC(C)=O)=C1

InChI Identifier

InChI=1S/C28H34O9/c1-16(15-36-17(2)29)9-7-5-6-8-10-18-13-19(11-12-20(18)30)26-25(33)24(32)23-22(37-26)14-21(31)27(34-3)28(23)35-4/h11-14,16,30-31,33H,5-10,15H2,1-4H3/t16-/m0/s1

InChI Key

PEZYILOZNWLRTK-INIZCTEOSA-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
Duranta erecta	LOTUS Database	35616633
Duranta repens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Fatty alcohol ester
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
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	4.95	ALOGPS
logP	4.79	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.75 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	138.63 m³·mol⁻¹	ChemAxon
Polarizability	56.59 Å³	ChemAxon
Number of Rings	3	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

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

162967842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone (NP0074598)

MOL for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

3D MOL for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

3D SDF for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

3D-SDF for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

PDB for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

3D PDB for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

SMILES for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

INCHI for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

Structure for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)

3D Structure for NP0074598 ((+)-3,7,4'-Trihydroxy-3'-(8''-acetoxy-7''-methyloctyl)-5,6-dimethoxyflavone)