NP-MRD: Showing NP-Card for (3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one (NP0330511)

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Record Information

Version

1.0

Created at

2022-09-12 15:56:14 UTC

Updated at

2022-09-12 15:56:14 UTC

NP-MRD ID

NP0330511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

Description

(3S)-3alpha-Isopropenyl-4abeta,5beta-dimethyl-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-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. (3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one is found in Ligularia kanaitzensis, Ligularia subspicata and Senecio linearifolius. It was first documented in 2002 (PMID: 12381112). Based on a literature review very few articles have been published on (3S)-3alpha-Isopropenyl-4abeta,5beta-dimethyl-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    2.9792   -0.8229   -1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9503   -0.7221   -0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2324   -0.5847    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7095   -0.7316    0.3139 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4549   -0.8669   -0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972   -0.2784    0.3290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6670   -0.8565    1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4625    1.1880    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469    1.5718    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    0.5356    1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880    0.7542    2.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    2.2166   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741    1.7704   -1.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004    0.3195   -1.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0223   -0.5569   -0.2777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2529    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.8074   -2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.9255   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    0.4533    0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1365   -1.2428    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -0.8981   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964   -1.5705    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.8753   -0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497   -0.1686   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.1607    2.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1061   -1.8340    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6800   -1.1213    2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844    2.6256    0.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.5656    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047    3.1248   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602    2.3617   -2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104    1.9246   -0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3394    0.1709   -2.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -0.0435   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1502   -1.6040   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    0.4396    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0112    0.1793    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5046   -1.1773    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  4  2  1  0
  2  3  1  0
  2  1  2  3
  6 15  1  0
  6  8  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  6
 14 33  1  0
 14 34  1  0
 13 31  1  0
 13 32  1  0
 12 29  1  0
 12 30  1  0
  9 28  1  0
  4 22  1  1
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv1652309122217562D          

 16 17  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0330511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC2=CC(=O)[C@@H](C[C@]12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11,13H,1,5-7,9H2,2-4H3/t11-,13-,15+/m0/s1

> <INCHI_KEY>
DIZRSLUNVNGBPA-CORIIIEPSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.234281328098056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aR,5S)-4a,5-dimethyl-3-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <JCHEM_LOGP>
3.9558039946666677

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.37167295417838

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9922309600814

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.0964

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,5S)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   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  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3a-Isopropenyl-4abeta,5b-dimethyl-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one	Generator
(3S)-3Α-isopropenyl-4abeta,5β-dimethyl-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one	Generator

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3400 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

(3S,4aR,5S)-4a,5-dimethyl-3-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

Traditional Name

(3S,4aR,5S)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC2=CC(=O)[C@@H](C[C@]12C)C(C)=C

InChI Identifier

InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11,13H,1,5-7,9H2,2-4H3/t11-,13-,15+/m0/s1

InChI Key

DIZRSLUNVNGBPA-CORIIIEPSA-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 kanaitzensis	LOTUS Database	35616633
Ligularia subspicata	LOTUS Database	35616633
Senecio linearifolius	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
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.96	ChemAxon
pKa (Strongest Acidic)	17.37	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.1 m³·mol⁻¹	ChemAxon
Polarizability	26.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

58828721

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14482759

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jang DS, Park EJ, Hawthorne ME, Vigo JS, Graham JG, Cabieses F, Santarsiero BD, Mesecar AD, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD: Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase. J Agric Food Chem. 2002 Oct 23;50(22):6330-4. doi: 10.1021/jf0206670. [PubMed:12381112 ]
LOTUS database [Link]

Showing NP-Card for (3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one (NP0330511)

MOL for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D MOL for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D SDF for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D-SDF for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

PDB for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D PDB for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

SMILES for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

INCHI for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

Structure for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D Structure for NP0330511 ((3s,4ar,5s)-4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)