NP-MRD: Showing NP-Card for 3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one (NP0171457)

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Record Information

Version

1.0

Created at

2022-09-03 07:59:16 UTC

Updated at

2022-09-03 07:59:17 UTC

NP-MRD ID

NP0171457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one

Description

Gigantetronenin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Gigantetronenin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gigantetronenin has been detected, but not quantified in, fruits. 3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one is found in Annona glabra, Annona muricata, Asimina longifolia, Goniothalamus giganteus and Xylopia aromatica. It was first documented in 2000 (PMID: 11413487). This could make gigantetronenin a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311162D          

 44 45  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 34 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 42 43  2  0
 28 44  1  0
 44 25  1  0
 42 37  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  0
 11 67  1  0
 12 68  1  0
 12 69  1  0
 13 70  1  0
 14 71  1  0
 15 72  1  0
 15 73  1  0
 16 74  1  0
 16 75  1  0
 17 76  1  6
 18 77  1  0
 19 78  1  6
 20 79  1  0
 21 80  1  0
 21 81  1  0
 22 82  1  0
 22 83  1  0
 23 84  1  6
 24 85  1  0
 25 86  1  6
 26 87  1  0
 26 88  1  0
 27 89  1  0
 27 90  1  0
 28 91  1  1
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  0
 32 99  1  0
 33100  1  0
 33101  1  0
 34102  1  6
 35103  1  0
 36104  1  0
 36105  1  0
 38106  1  0
 39107  1  1
 40108  1  0
 40109  1  0
 40110  1  0
M  END


  Mrv0541 05061311162D          

 44 45  0  0  0  0            999 V2000
    4.1082   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2961   31.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8227   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9661   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6805   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3950   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1095   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8239   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5384   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2529   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9674   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6818   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3963   17.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3010   25.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9654   26.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8161   24.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1108   17.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4503   27.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1516   24.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1108   18.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8417   23.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5397   20.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5397   21.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5867   22.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6766   29.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5997   28.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1246   30.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2641   29.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1148   27.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6667   23.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8252   19.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8252   19.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2542   21.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2542   22.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4572   29.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943   27.9240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5397   18.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1108   20.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9687   21.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8441   28.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3709   30.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9216   22.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 25 24  1  0  0  0  0
 26 23  1  0  0  0  0
 29  2  1  0  0  0  0
 29 27  1  0  0  0  0
 30 27  2  0  0  0  0
 30 28  1  0  0  0  0
 31 20  1  0  0  0  0
 31 28  1  0  0  0  0
 32 21  1  0  0  0  0
 32 23  1  0  0  0  0
 33 22  1  0  0  0  0
 34 24  1  0  0  0  0
 34 33  1  0  0  0  0
 35 25  1  0  0  0  0
 36 26  1  0  0  0  0
 36 35  1  0  0  0  0
 37 30  1  0  0  0  0
 38 31  1  0  0  0  0
 39 33  1  0  0  0  0
 40 34  1  0  0  0  0
 41 35  1  0  0  0  0
 42 37  2  0  0  0  0
 43 29  1  0  0  0  0
 43 37  1  0  0  0  0
 44 32  1  0  0  0  0
 44 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C\CCC(O)C(O)CCC(O)C1CCC(CCCCCC(O)CC2=CC(C)OC2=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-33(39)34(40)24-25-35(41)36-26-23-32(44-36)21-18-16-17-20-31(38)28-30-27-29(2)43-37(30)42/h14-15,27,29,31-36,38-41H,3-13,16-26,28H2,1-2H3/b15-14+

> <INCHI_KEY>
LFIZQGRMDGWRQH-CCEZHUSRSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
77.65526096932297

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-hydroxy-7-{5-[(8E)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
7.05

> <JCHEM_LOGP>
8.233470311333335

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.255390135762887

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.69106604824016

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022876858394

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
179.66179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-7-{5-[(8E)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.669  33.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.286  58.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.002  32.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.336  33.166   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.670  32.396   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.003  33.166   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.337  32.396   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.671  33.166   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.004  32.396   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.338  33.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.672  32.396   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.005  33.166   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.339  32.396   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.673  33.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.006  32.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.295  47.904   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.669  49.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.390  46.658   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.340  33.166   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.574  50.557   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.016  45.252   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.340  34.706   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.571  44.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.007  37.786   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.007  39.326   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.095  42.541   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.996  55.950   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.853  53.210   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      31.966  57.095   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.226  54.617   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.948  51.964   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.111  44.006   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.674  35.476   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.674  37.016   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      30.341  40.096   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      30.341  41.636   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.720  54.937   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      30.416  52.125   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      29.007  34.706   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      26.340  37.786   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      31.675  39.326   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      29.576  53.906   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      30.559  56.468   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      31.587  42.541   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   29                                                            
CONECT    3    1    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   19                                                       
CONECT   16   17   18                                                       
CONECT   17   16   20                                                       
CONECT   18   16   21                                                       
CONECT   19   15   22                                                       
CONECT   20   17   31                                                       
CONECT   21   18   32                                                       
CONECT   22   19   33                                                       
CONECT   23   26   32                                                       
CONECT   24   25   34                                                       
CONECT   25   24   35                                                       
CONECT   26   23   36                                                       
CONECT   27   29   30                                                       
CONECT   28   30   31                                                       
CONECT   29    2   27   43                                                  
CONECT   30   27   28   37                                                  
CONECT   31   20   28   38                                                  
CONECT   32   21   23   44                                                  
CONECT   33   22   34   39                                                  
CONECT   34   24   33   40                                                  
CONECT   35   25   36   41                                                  
CONECT   36   26   35   44                                                  
CONECT   37   30   42   43                                                  
CONECT   38   31                                                            
CONECT   39   33                                                            
CONECT   40   34                                                            
CONECT   41   35                                                            
CONECT   42   37                                                            
CONECT   43   29   37                                                       
CONECT   44   32   36                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Value	Source
Gigantrionenin	HMDB
Gigantetronenin	MeSH

Chemical Formula

C₃₇H₆₆O₇

Average Mass

622.9157 Da

Monoisotopic Mass

622.48085 Da

IUPAC Name

3-(2-hydroxy-7-{5-[(8E)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(2-hydroxy-7-{5-[(8E)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC\C=C\CCC(O)C(O)CCC(O)C1CCC(CCCCCC(O)CC2=CC(C)OC2=O)O1

InChI Identifier

InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-33(39)34(40)24-25-35(41)36-26-23-32(44-36)21-18-16-17-20-31(38)28-30-27-29(2)43-37(30)42/h14-15,27,29,31-36,38-41H,3-13,16-26,28H2,1-2H3/b15-14+

InChI Key

LFIZQGRMDGWRQH-CCEZHUSRSA-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
Annona glabra	LOTUS Database	35616633
Annona muricata	LOTUS Database	35616633
Asimina longifolia	LOTUS Database	35616633
Goniothalamus giganteus	LOTUS Database	35616633
Xylopia aromatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
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	7.05	ALOGPS
logP	8.23	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	179.66 m³·mol⁻¹	ChemAxon
Polarizability	77.66 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

HMDB0039608

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019235

KNApSAcK ID

Not Available

Chemspider ID

4943887

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for 3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one (NP0171457)

MOL for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

3D MOL for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

3D SDF for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

3D-SDF for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

PDB for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

3D PDB for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

SMILES for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

INCHI for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

Structure for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)

3D Structure for NP0171457 (3-(2-hydroxy-7-{5-[(8e)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl}heptyl)-5-methyl-5h-furan-2-one)