NP-MRD: Showing NP-Card for (2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one (NP0146888)

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Record Information

Version

2.0

Created at

2022-09-02 02:22:52 UTC

Updated at

2022-09-02 02:22:52 UTC

NP-MRD ID

NP0146888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one

Description

Kotolactone A belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. (2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one is found in Cinnamomum kotoense. Based on a literature review very few articles have been published on Kotolactone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204222D          

 37 38  0  0  1  0            999 V2000
  -12.5870    2.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1785    3.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3939    3.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9962    3.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022204222D          

 37 38  0  0  1  0            999 V2000
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   -4.9854    4.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007    3.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5876    4.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030    4.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    4.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    5.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    4.2660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    3.4814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8981    3.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    2.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    2.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1356    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8657    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5802    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4381    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030    2.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    3.4814    0.0000 C   0  0  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 22 36  1  0  0  0  0
 37 36  1  1  0  0  0
 15 37  1  0  0  0  0
 19 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC\C=C1/[C@@H]2O[C@@H](CCCCCCCCCCCCC)O[C@]2(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H60O4/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33(3,37-32(29)34)36-30(35-31)28-26-24-22-20-17-15-13-11-9-7-5-2/h27,30-31H,4-26,28H2,1-3H3/b29-27+/t30-,31+,33-/m1/s1

> <INCHI_KEY>
XOBIKJVESDPFSM-ZSUQRGCCSA-N

> <FORMULA>
C33H60O4

> <MOLECULAR_WEIGHT>
520.839

> <EXACT_MASS>
520.449160412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
68.71969430460697

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3aR,6E,6aS)-3a-methyl-6-tetradecylidene-2-tridecyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-one

> <ALOGPS_LOGP>
10.21

> <JCHEM_LOGP>
12.501984232999996

> <ALOGPS_LOGS>
-7.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.174634449109016

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
155.0957

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3aR,6E,6aS)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0     -23.496   4.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -22.351   5.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -20.887   4.636   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -19.742   5.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -18.278   5.190   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -17.133   6.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -15.669   5.745   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -14.524   6.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.060   6.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.915   7.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.450   6.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.306   7.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.841   7.409   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.697   8.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.232   7.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.986   8.868   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.986  10.408   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.741   7.963   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.216   6.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.676   6.499   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.741   5.034   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.986   4.129   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.986   2.589   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.653   1.819   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.319   2.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.015   1.819   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.348   2.589   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.682   1.819   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.016   2.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.349   1.819   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.683   2.589   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.017   1.819   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.350   2.589   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.684   1.819   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.018   2.589   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.232   5.034   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.756   6.499   0.000  0.00  0.00           C+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   37                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   37                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   22   37                                                       
CONECT   37   36   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₆₀O₄

Average Mass

520.8390 Da

Monoisotopic Mass

520.44916 Da

IUPAC Name

(2R,3aR,6E,6aS)-3a-methyl-6-tetradecylidene-2-tridecyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-one

Traditional Name

(2R,3aR,6E,6aS)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C1/[C@@H]2O[C@@H](CCCCCCCCCCCCC)O[C@]2(C)OC1=O

InChI Identifier

InChI=1S/C33H60O4/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33(3,37-32(29)34)36-30(35-31)28-26-24-22-20-17-15-13-11-9-7-5-2/h27,30-31H,4-26,28H2,1-3H3/b29-27+/t30-,31+,33-/m1/s1

InChI Key

XOBIKJVESDPFSM-ZSUQRGCCSA-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
Cinnamomum kotoense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Gamma butyrolactone
Meta-dioxolane
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
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	10.21	ALOGPS
logP	12.5	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	155.1 m³·mol⁻¹	ChemAxon
Polarizability	68.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

9795347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11620599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one (NP0146888)

MOL for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

3D MOL for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

3D SDF for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

3D-SDF for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

PDB for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

3D PDB for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

SMILES for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

INCHI for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

Structure for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)

3D Structure for NP0146888 ((2r,3ar,6e,6as)-3a-methyl-6-tetradecylidene-2-tridecyl-dihydrofuro[2,3-d][1,3]dioxol-5-one)