NP-MRD: Showing NP-Card for Manoalide monoacetate (NP0076840)

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Record Information

Version

2.0

Created at

2022-04-28 22:01:43 UTC

Updated at

2022-04-28 22:01:43 UTC

NP-MRD ID

NP0076840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Manoalide monoacetate

Description

(2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Manoalide monoacetate is found in Luffariella variabilis. Based on a literature review very few articles have been published on (2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200012D          

 33 35  0  0  1  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -8.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -9.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -8.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -7.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4521   -7.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652   -8.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -7.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936   -9.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
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  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 25 32  1  0  0  0  0
 21 33  1  0  0  0  0
M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
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    1.0940    1.0288   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0416    1.6022    1.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2465   -0.4687    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183    1.8767    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    1.7319   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0345    0.4795   -0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.2030   -1.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6281    0.3454   -2.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3214   -1.4921   -1.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5142   -1.8829   -1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0305   -0.2687    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203    2.6923    1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2737   -0.8050    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476    2.9486    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292200012D          

 33 35  0  0  1  0            999 V2000
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  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
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 29 30  1  0  0  0  0
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 25 32  1  0  0  0  0
 21 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1OC(=O)C=C1[C@@H]1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)[C@@H](O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O5/c1-18(11-14-24-19(2)9-7-15-28(24,4)5)8-6-10-21-12-13-22(16-25(21)30)23-17-26(31)33-27(23)32-20(3)29/h8,12,17,22,25,27,30H,6-7,9-11,13-16H2,1-5H3/b18-8+/t22-,25+,27+/m1/s1

> <INCHI_KEY>
YFPJKEBHMGIVPZ-CAEINODZSA-N

> <FORMULA>
C28H40O5

> <MOLECULAR_WEIGHT>
456.623

> <EXACT_MASS>
456.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.934943655460046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

> <ALOGPS_LOGP>
5.29

> <JCHEM_LOGP>
5.684342195999999

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.56581610210787

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3554624803641806

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2391235198692025

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
132.086

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2H-furan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770 -16.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.675 -17.476   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.770 -16.230   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.711 -14.289   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.855 -15.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.320 -14.844   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.535 -16.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-[(1R,5S)-5-Hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2,5-dihydrofuran-2-yl acetic acid	Generator

Chemical Formula

C₂₈H₄₀O₅

Average Mass

456.6230 Da

Monoisotopic Mass

456.28757 Da

IUPAC Name

(2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

Traditional Name

(2S)-3-[(1R,5S)-5-hydroxy-4-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]cyclohex-3-en-1-yl]-5-oxo-2H-furan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1OC(=O)C=C1[C@@H]1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)[C@@H](O)C1

InChI Identifier

InChI=1S/C28H40O5/c1-18(11-14-24-19(2)9-7-15-28(24,4)5)8-6-10-21-12-13-22(16-25(21)30)23-17-26(31)33-27(23)32-20(3)29/h8,12,17,22,25,27,30H,6-7,9-11,13-16H2,1-5H3/b18-8+/t22-,25+,27+/m1/s1

InChI Key

YFPJKEBHMGIVPZ-CAEINODZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Luffariella variabilis	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Acylal
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.29	ALOGPS
logP	5.68	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.09 m³·mol⁻¹	ChemAxon
Polarizability	52.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

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

163106708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Manoalide monoacetate (NP0076840)

MOL for NP0076840 (Manoalide monoacetate)

3D MOL for NP0076840 (Manoalide monoacetate)

3D SDF for NP0076840 (Manoalide monoacetate)

3D-SDF for NP0076840 (Manoalide monoacetate)

PDB for NP0076840 (Manoalide monoacetate)

3D PDB for NP0076840 (Manoalide monoacetate)

SMILES for NP0076840 (Manoalide monoacetate)

INCHI for NP0076840 (Manoalide monoacetate)

Structure for NP0076840 (Manoalide monoacetate)

3D Structure for NP0076840 (Manoalide monoacetate)