NP-MRD: Showing NP-Card for [(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate (NP0179334)

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Record Information

Version

2.0

Created at

2022-09-03 17:30:13 UTC

Updated at

2022-09-03 17:30:13 UTC

NP-MRD ID

NP0179334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate

Description

Stearoyldelicone belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. [(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate is found in Russula delica. Based on a literature review very few articles have been published on Stearoyldelicone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032219302D          

 36 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652309032219302D          

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    8.0659  -13.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7804  -14.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4948  -13.9312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0099  -13.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8304  -14.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6509  -14.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8224  -13.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1079  -13.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6070  -13.5367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1577  -12.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1591  -12.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7721  -13.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2201  -14.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0486  -14.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6617  -15.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2640  -15.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0924  -15.9577    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  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0179334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)OC[C@]1(C)CC2=C(C1)[C@@]1(C)CCC1=C(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H54O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-30(34)36-25-32(3)23-27-29(24-32)33(4)22-21-28(33)26(2)31(27)35/h5-25H2,1-4H3/t32-,33+/m1/s1

> <INCHI_KEY>
UTSRTAUYLDAFIC-SAIUNTKASA-N

> <FORMULA>
C33H54O3

> <MOLECULAR_WEIGHT>
498.792

> <EXACT_MASS>
498.407295599

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
64.42348543847648

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(6S,7bS)-3,6,7b-trimethyl-4-oxo-1H,2H,4H,5H,6H,7H,7bH-cyclobuta[e]inden-6-yl]methyl octadecanoate

> <JCHEM_LOGP>
9.982334134000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.124365410599039

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
151.3243

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(6S,7bS)-3,6,7b-trimethyl-4-oxo-1H,2H,5H,7H-cyclobuta[e]inden-6-yl]methyl octadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.950 -26.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.616 -26.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.283 -26.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.949 -26.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.615 -26.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.281 -26.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.948 -26.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.386 -26.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.720 -26.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.053 -26.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.387 -26.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.721 -26.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.054 -26.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.388 -26.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.722 -26.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.055 -26.775   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.389 -26.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.723 -26.775   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.723 -28.315   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      15.056 -26.005   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      16.390 -26.775   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.724 -26.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.818 -24.759   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.350 -27.412   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.882 -27.251   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.202 -25.744   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.868 -24.974   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.666 -25.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.828 -23.977   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.697 -24.124   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.841 -25.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.811 -26.299   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.491 -27.805   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.635 -28.836   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.026 -28.281   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      20.706 -29.788   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29   30   32                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   25   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₅₄O₃

Average Mass

498.7920 Da

Monoisotopic Mass

498.40730 Da

IUPAC Name

[(6S,7bS)-3,6,7b-trimethyl-4-oxo-1H,2H,4H,5H,6H,7H,7bH-cyclobuta[e]inden-6-yl]methyl octadecanoate

Traditional Name

[(6S,7bS)-3,6,7b-trimethyl-4-oxo-1H,2H,5H,7H-cyclobuta[e]inden-6-yl]methyl octadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OC[C@]1(C)CC2=C(C1)[C@@]1(C)CCC1=C(C)C2=O

InChI Identifier

InChI=1S/C33H54O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-30(34)36-25-32(3)23-27-29(24-32)33(4)22-21-28(33)26(2)31(27)35/h5-25H2,1-4H3/t32-,33+/m1/s1

InChI Key

UTSRTAUYLDAFIC-SAIUNTKASA-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
Russula delica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Illudanes and illudins

Alternative Parents

Substituents

Illudane sesquiterpenoid
Fatty acid ester
Fatty acyl
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	9.98	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	151.32 m³·mol⁻¹	ChemAxon
Polarizability	64.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

78438007

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15834292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate (NP0179334)

MOL for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

3D MOL for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

3D SDF for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

3D-SDF for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

PDB for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

3D PDB for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

SMILES for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

INCHI for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

Structure for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)

3D Structure for NP0179334 ([(6s,7bs)-3,6,7b-trimethyl-4-oxo-1h,2h,5h,7h-cyclobuta[e]inden-6-yl]methyl octadecanoate)