NP-MRD: Showing NP-Card for (4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one (NP0200265)

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Record Information

Version

2.0

Created at

2022-09-04 19:03:57 UTC

Updated at

2022-09-04 19:03:57 UTC

NP-MRD ID

NP0200265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one

Description

(4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one is found in Ligularia virgaurea.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221042D          

 35 39  0  0  1  0            999 V2000
    1.5983   -0.4834    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


  Mrv1652309042221042D          

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  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 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
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
  4 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0200265

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC[C@@H]2C[C@]3(O)OC(=O)C(C)=C3[C@@H](C(=O)C(C)=C3C[C@]4(C)[C@@H](C)CCCC4=CC3=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O5/c1-16-9-7-11-20-13-23(31)22(15-28(16,20)5)18(3)26(32)25-24-19(4)27(33)35-30(24,34)14-21-12-8-10-17(2)29(21,25)6/h13,16-17,21,25,34H,7-12,14-15H2,1-6H3/b22-18+/t16-,17-,21+,25-,28+,29+,30-/m0/s1

> <INCHI_KEY>
UVWVSOFBRYDOJR-HXSCCECRSA-N

> <FORMULA>
C30H40O5

> <MOLECULAR_WEIGHT>
480.645

> <EXACT_MASS>
480.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.907362055635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aR,5S,8aR,9aS)-4-{2-[(2Z,8S,8aR)-8,8a-dimethyl-3-oxo-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_LOGP>
6.341185891333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.988050702995675

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.80516953583313

> <JCHEM_PKA_STRONGEST_BASIC>
-4.445172568230622

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
136.5192

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,8aR,9aS)-4-{2-[(2Z,8S,8aR)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1H-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.983  -0.902   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.626  -2.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.626  -0.702   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.960   0.068   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.755   0.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.222  -1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.422   2.408   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.756   0.098   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.556  -1.904   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.222  -2.674   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  C   UNK     0       7.586  -2.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.591  -1.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591  -4.383   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  O   UNK     0       4.763  -5.914   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    3   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₅

Average Mass

480.6450 Da

Monoisotopic Mass

480.28757 Da

IUPAC Name

(4S,4aR,5S,8aR,9aS)-4-{2-[(2Z,8S,8aR)-8,8a-dimethyl-3-oxo-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4S,4aR,5S,8aR,9aS)-4-{2-[(2Z,8S,8aR)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1H-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC[C@@H]2C[C@]3(O)OC(=O)C(C)=C3[C@@H](C(=O)C(C)=C3C[C@]4(C)[C@@H](C)CCCC4=CC3=O)[C@]12C

InChI Identifier

InChI=1S/C30H40O5/c1-16-9-7-11-20-13-23(31)22(15-28(16,20)5)18(3)26(32)25-24-19(4)27(33)35-30(24,34)14-21-12-8-10-17(2)29(21,25)6/h13,16-17,21,25,34H,7-12,14-15H2,1-6H3/b22-18+/t16-,17-,21+,25-,28+,29+,30-/m0/s1

InChI Key

UVWVSOFBRYDOJR-HXSCCECRSA-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 virgaurea	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	6.34	ChemAxon
pKa (Strongest Acidic)	10.81	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.52 m³·mol⁻¹	ChemAxon
Polarizability	53.91 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one (NP0200265)

MOL for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D MOL for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D SDF for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D-SDF for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

PDB for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D PDB for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

SMILES for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

INCHI for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

Structure for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D Structure for NP0200265 ((4s,4ar,5s,8ar,9as)-4-{2-[(2z,8s,8ar)-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1h-naphthalen-2-ylidene]propanoyl}-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)