NP-MRD: Showing NP-Card for 4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one (NP0197602)

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Record Information

Version

2.0

Created at

2022-09-04 15:53:54 UTC

Updated at

2022-09-04 15:53:55 UTC

NP-MRD ID

NP0197602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one

Description

4-[2-(8,8A-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. 4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)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. 4-[2-(8,8A-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261513152D          

 35 39  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004261513152D          

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    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0197602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(=O)C1C2=C(C)C(=O)OC2(O)CC2CCCC(C)C12C)C1=CC2(C)C(C)CCCC2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O5/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/h15-18,20-21,25,34H,7-14H2,1-6H3

> <INCHI_KEY>
GWHMEAPEDZSTOU-UHFFFAOYSA-N

> <FORMULA>
C30H42O5

> <MOLECULAR_WEIGHT>
482.661

> <EXACT_MASS>
482.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.0593887288432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
6.174710869

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.845603958254685

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.695458004996057

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444963591824952

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
135.9332

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)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                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.145  -3.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.652  -3.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.519  -4.747   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.289  -6.081   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.988  -4.586   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.421  -3.985   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    5   15   22                                             
CONECT   22   21                                                            
CONECT   23    2   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   32                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   23   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

C₃₀H₄₂O₅

Average Mass

482.6610 Da

Monoisotopic Mass

482.30322 Da

IUPAC Name

4-[2-(8,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)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

4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)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

CC(C(=O)C1C2=C(C)C(=O)OC2(O)CC2CCCC(C)C12C)C1=CC2(C)C(C)CCCC2CC1=O

InChI Identifier

InChI=1S/C30H42O5/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/h15-18,20-21,25,34H,7-14H2,1-6H3

InChI Key

GWHMEAPEDZSTOU-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 virgaurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoid skeleton
Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Eremophilane sesquiterpenoid
Naphthofuran
Cyclohexenone
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.43	ALOGPS
logP	6.17	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.7	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	3	ChemAxon
Refractivity	135.93 m³·mol⁻¹	ChemAxon
Polarizability	54.06 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

74340728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one (NP0197602)

MOL for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D MOL for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D SDF for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D-SDF for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

PDB for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D PDB for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

SMILES for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

INCHI for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

Structure for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)

3D Structure for NP0197602 (4-[2-(8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)propanoyl]-9a-hydroxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-2-one)