NP-MRD: Showing NP-Card for 1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone (NP0240764)

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Record Information

Version

2.0

Created at

2022-09-07 00:40:07 UTC

Updated at

2022-09-07 00:40:07 UTC

NP-MRD ID

NP0240764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone

Description

1-[3-({9-Hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethan-1-one belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone is found in Ligularia muliensis. 1-[3-({9-Hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171515372D          

 33 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171515372D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 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  0  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  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 31  2  0  0  0  0
 31 32  1  0  0  0  0
 17 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2C(O)C3=C(CC12C)C(C)=C(OC1=C(CC2(C)C(C)CCCC2C1)C(C)=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O4/c1-16-9-7-11-20-13-24(22(19(4)30)15-28(16,20)5)32-27-18(3)21-14-29(6)17(2)10-8-12-23(29)25(31)26(21)33-27/h16-17,20,23,25,31H,7-15H2,1-6H3

> <INCHI_KEY>
NZBIQFAHPKZEGM-UHFFFAOYSA-N

> <FORMULA>
C29H42O4

> <MOLECULAR_WEIGHT>
454.651

> <EXACT_MASS>
454.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.56459811955935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[3-({9-hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethan-1-one

> <ALOGPS_LOGP>
5.89

> <JCHEM_LOGP>
6.182655456000002

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.10468183355437

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.207521839790676

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8458582173943188

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
131.2266

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[3-({9-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1H-naphthalen-2-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -3.606  -8.948   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.066  -8.948   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.296 -10.281   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.244 -10.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.014  -8.948   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.244  -7.614   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.014  -6.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.244  -4.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.296  -4.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.066  -6.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.296  -7.614   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.836  -7.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.066  -3.613   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.606  -3.613   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.296  -2.279   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591  -5.923   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    6   12                                             
CONECT   12   11                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   19   32                                                  
CONECT   32   31   17   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₄

Average Mass

454.6510 Da

Monoisotopic Mass

454.30831 Da

IUPAC Name

1-[3-({9-hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethan-1-one

Traditional Name

1-[3-({9-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1H-naphthalen-2-yl]ethanone

CAS Registry Number

Not Available

SMILES

CC1CCCC2C(O)C3=C(CC12C)C(C)=C(OC1=C(CC2(C)C(C)CCCC2C1)C(C)=O)O3

InChI Identifier

InChI=1S/C29H42O4/c1-16-9-7-11-20-13-24(22(19(4)30)15-28(16,20)5)32-27-18(3)21-14-29(6)17(2)10-8-12-23(29)25(31)26(21)33-27/h16-17,20,23,25,31H,7-15H2,1-6H3

InChI Key

NZBIQFAHPKZEGM-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
Ligularia muliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Furan
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
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	5.89	ALOGPS
logP	6.18	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.23 m³·mol⁻¹	ChemAxon
Polarizability	53.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

75169399

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone (NP0240764)

MOL for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

3D MOL for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

3D SDF for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

3D-SDF for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

PDB for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

3D PDB for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

SMILES for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

INCHI for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

Structure for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)

3D Structure for NP0240764 (1-[3-({9-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-yl}oxy)-8,8a-dimethyl-4,4a,5,6,7,8-hexahydro-1h-naphthalen-2-yl]ethanone)