NP-MRD: Showing NP-Card for 7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one (NP0212391)

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Record Information

Version

2.0

Created at

2022-09-05 11:02:38 UTC

Updated at

2022-09-05 11:02:38 UTC

NP-MRD ID

NP0212391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one

Description

Pectachol belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Pectachol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Pectachol has been detected, but not quantified in, tea. 7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one is found in Achillea pseudopectinata, Agrobacterium rhizogenes, Artemisia abrotanum and Cotula cinerea. This could make pectachol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310492D          

 32 35  0  0  0  0            999 V2000
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    0.8986    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061310492D          

 32 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0212391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OCC2C(=C)CCC3C(C)(C)C(O)CCC23C)C(OC)=C2OC(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-15-7-9-19-25(2,3)20(27)11-12-26(19,4)17(15)14-31-23-18(29-5)13-16-8-10-21(28)32-22(16)24(23)30-6/h8,10,13,17,19-20,27H,1,7,9,11-12,14H2,2-6H3

> <INCHI_KEY>
QISGCNZPAGFKFT-UHFFFAOYSA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.5446

> <EXACT_MASS>
442.23553882

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.400799759623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methoxy]-6,8-dimethoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
4.019754261333333

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489413240225527

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8350316596938198

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
122.52059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.677   4.980   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.657   4.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  17.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   8.470   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  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  16.170   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       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   6.930   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  17.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.335  18.480   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001  13.090   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7    9   15                                                       
CONECT    8   10   16                                                       
CONECT    9    7   19                                                       
CONECT   10    8   21                                                       
CONECT   11   12   20                                                       
CONECT   12   11   26                                                       
CONECT   13   16   18                                                       
CONECT   14   17   31                                                       
CONECT   15    1    7   17                                                  
CONECT   16    8   13   22                                                  
CONECT   17   14   15   26                                                  
CONECT   18   13   23   29                                                  
CONECT   19    9   25   26                                                  
CONECT   20   11   25   27                                                  
CONECT   21   10   28   32                                                  
CONECT   22   16   24   32                                                  
CONECT   23   18   24   31                                                  
CONECT   24   22   23   30                                                  
CONECT   25    2    3   19   20                                             
CONECT   26    4   12   17   19                                             
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29    5   18                                                       
CONECT   30    6   24                                                       
CONECT   31   14   23                                                       
CONECT   32   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5446 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methoxy]-6,8-dimethoxy-2H-chromen-2-one

Traditional Name

7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(OCC2C(=C)CCC3C(C)(C)C(O)CCC23C)C(OC)=C2OC(=O)C=CC2=C1

InChI Identifier

InChI=1S/C26H34O6/c1-15-7-9-19-25(2,3)20(27)11-12-26(19,4)17(15)14-31-23-18(29-5)13-16-8-10-21(28)32-22(16)24(23)30-6/h8,10,13,17,19-20,27H,1,7,9,11-12,14H2,2-6H3

InChI Key

QISGCNZPAGFKFT-UHFFFAOYSA-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
Achillea pseudopectinata	LOTUS Database	35616633
Agrobacterium rhizogenes	LOTUS Database	35616633
Artemisia abrotanum	LOTUS Database	35616633
Cotula cinerea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	4.79	ALOGPS
logP	4.02	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.52 m³·mol⁻¹	ChemAxon
Polarizability	48.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039064

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018562

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

78178168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one (NP0212391)

MOL for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

3D MOL for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

3D SDF for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

3D-SDF for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

PDB for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

3D PDB for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

SMILES for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

INCHI for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

Structure for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)

3D Structure for NP0212391 (7-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methoxy]-6,8-dimethoxychromen-2-one)