NP-MRD: Showing NP-Card for 2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate (NP0330103)

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Record Information

Version

2.0

Created at

2022-09-12 15:08:33 UTC

Updated at

2022-09-12 15:08:33 UTC

NP-MRD ID

NP0330103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate

Description

2-(Acetyloxy)-5-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl acetate belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. 2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate is found in Helminthostachys zeylanica. Based on a literature review very few articles have been published on 2-(acetyloxy)-5-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217082D          

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M  END

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M  END


  Mrv1652309122217082D          

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 16 21  2  0  0  0  0
  8 21  1  0  0  0  0
  7 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  3 28  2  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@H]2C(=O)CCCC2(C)C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O9/c1-15(30)36-22-9-8-17(11-25(22)37-16(2)31)23-13-21(33)27-26(38-23)14-24(35-5)18(28(27)34)12-19-20(32)7-6-10-29(19,3)4/h8-9,11,13-14,19,34H,6-7,10,12H2,1-5H3/t19-/m0/s1

> <INCHI_KEY>
UXFOPNAVDQIGLR-IBGZPJMESA-N

> <FORMULA>
C29H30O9

> <MOLECULAR_WEIGHT>
522.55

> <EXACT_MASS>
522.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.51697903112279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(acetyloxy)-4-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl acetate

> <JCHEM_LOGP>
4.594044041

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.04205596252272

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.21010320326318

> <JCHEM_PKA_STRONGEST_BASIC>
-4.749061076640342

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
138.1637

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-4-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.150  -4.084   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.873  -5.336   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16    8                                                       
CONECT   22    7   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   30   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-5-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl acetic acid	Generator

Chemical Formula

C₂₉H₃₀O₉

Average Mass

522.5500 Da

Monoisotopic Mass

522.18898 Da

IUPAC Name

2-(acetyloxy)-4-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl acetate

Traditional Name

2-(acetyloxy)-4-(6-{[(1R)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@H]2C(=O)CCCC2(C)C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1

InChI Identifier

InChI=1S/C29H30O9/c1-15(30)36-22-9-8-17(11-25(22)37-16(2)31)23-13-21(33)27-26(38-23)14-24(35-5)18(28(27)34)12-19-20(32)7-6-10-29(19,3)4/h8-9,11,13-14,19,34H,6-7,10,12H2,1-5H3/t19-/m0/s1

InChI Key

UXFOPNAVDQIGLR-IBGZPJMESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Helminthostachys zeylanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

6-prenylated flavones

Alternative Parents

Substituents

6-prenylated flavone
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Chromone
Benzopyran
Phenol ester
1-benzopyran
Phenoxy compound
Anisole
Alkyl aryl ether
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Cyclic ketone
Carboxylic acid ester
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Organic oxide
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen 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	4.59	ChemAxon
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	138.16 m³·mol⁻¹	ChemAxon
Polarizability	55.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

162960516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate (NP0330103)

MOL for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

3D MOL for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

3D SDF for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

3D-SDF for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

PDB for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

3D PDB for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

SMILES for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

INCHI for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

Structure for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)

3D Structure for NP0330103 (2-(acetyloxy)-4-(6-{[(1r)-2,2-dimethyl-6-oxocyclohexyl]methyl}-5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl acetate)