NP-MRD: Showing NP-Card for (4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione (NP0261119)

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Record Information

Version

2.0

Created at

2022-09-08 03:28:55 UTC

Updated at

2022-09-08 03:28:55 UTC

NP-MRD ID

NP0261119

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione

Description

9-Oxo-10,11-dehydroageraphorone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione is found in Ageratina adenophora. (4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione was first documented in 2018 (PMID: 28880111). Based on a literature review a small amount of articles have been published on 9-Oxo-10,11-dehydroageraphorone (PMID: 32929734) (PMID: 32250541).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5846    3.3099    1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205    1.8706    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    1.6002   -0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2252    0.2044   -0.6770 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1199   -0.2143   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803    0.5059   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -0.1299    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    1.9500   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568   -1.6823    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895   -2.1280    0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -2.4977   -0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423   -2.1211   -0.5613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9047   -2.3905   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -0.7322   -0.0883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3370   -0.5646    1.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5863    0.8532    1.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305    1.2351    2.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    3.3784    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963    3.6355    2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    3.9735    0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679    2.4455   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564    0.0490   -1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -0.4147    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753    0.5716    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -1.0734   -0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    2.4681    0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.3728   -0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    2.1853   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4978   -2.2827   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -3.5938   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221   -2.8443    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789   -3.5023   -1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2913   -2.1142   -2.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -1.9297   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999   -0.3687   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861   -0.8863    1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070   -1.1384    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
 14 12  1  0
 14  4  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 12 31  1  1
 11 29  1  0
 11 30  1  0
  4 22  1  6
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 15 36  1  0
 15 37  1  0
 14 35  1  6
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
M  END


  Mrv1652309082205282D          

 17 18  0  0  1  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0261119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(=O)C([C@@H]2C=C(C)C(=O)C[C@H]12)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-8(2)15-12-5-10(4)13(16)7-11(12)9(3)6-14(15)17/h5,9,11-12H,6-7H2,1-4H3/t9-,11+,12+/m0/s1

> <INCHI_KEY>
RDQAKTSDUZUBQC-MVWJERBFSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.738643922047395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,8aS)-4,7-dimethyl-1-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene-2,6-dione

> <JCHEM_LOGP>
3.070123150333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.561163624309082

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
69.7182

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,8aS)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3H-naphthalene-2,6-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(4S,4aR,8aS)-4,7-dimethyl-1-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene-2,6-dione

Traditional Name

(4S,4aR,8aS)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3H-naphthalene-2,6-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1CC(=O)C([C@@H]2C=C(C)C(=O)C[C@H]12)=C(C)C

InChI Identifier

InChI=1S/C15H20O2/c1-8(2)15-12-5-10(4)13(16)7-11(12)9(3)6-14(15)17/h5,9,11-12H,6-7H2,1-4H3/t9-,11+,12+/m0/s1

InChI Key

RDQAKTSDUZUBQC-MVWJERBFSA-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
Ageratina adenophora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane 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	3.07	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.72 m³·mol⁻¹	ChemAxon
Polarizability	26.74 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

C00020224

Chemspider ID

57577001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131636964

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Luo SH, Hua J, Li DS, Ling Y, Luo Q, Li SH: Characterization of defensive cadinenes and a novel sesquiterpene synthase responsible for their biosynthesis from the invasive Eupatorium adenophorum. New Phytol. 2021 Feb;229(3):1740-1754. doi: 10.1111/nph.16925. Epub 2020 Oct 14. [PubMed:32929734 ]
Zhou X, Wang J, Sun L, Xiang A, Shi Q, Li H, Zhou D, Ge F: An efficient, green, and easy-to-scale-up strategy for target-oriented isolating cadinene sesquiterpenoids from Eupatorium adenophorum Spreng. J Sep Sci. 2020 Jul;43(13):2646-2656. doi: 10.1002/jssc.201901245. Epub 2020 May 5. [PubMed:32250541 ]
Xu R, Weng J, Hu L, Peng G, Ren Z, Deng J, Jia Y, Wang C, He H, Hu Y: Anti-NDV activity of 9-oxo10,11-dehydroageraphorone extracted from Eupatorium adenophorum Spreng in vitro. Nat Prod Res. 2018 Sep;32(18):2244-2247. doi: 10.1080/14786419.2017.1371158. Epub 2017 Sep 7. [PubMed:28880111 ]
LOTUS database [Link]

Showing NP-Card for (4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione (NP0261119)

MOL for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

3D MOL for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

3D SDF for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

3D-SDF for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

PDB for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

3D PDB for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

SMILES for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

INCHI for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

Structure for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)

3D Structure for NP0261119 ((4s,4ar,8as)-4,7-dimethyl-1-(propan-2-ylidene)-4,4a,5,8a-tetrahydro-3h-naphthalene-2,6-dione)