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Showing NP-Card for 9-Hydroxyasimicinone (NP0335202)

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Record Information
Version2.0
Created at2024-09-11 00:31:37 UTC
Updated at2024-09-11 00:31:37 UTC
NP-MRD IDNP0335202
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Hydroxyasimicinone
Description9-Hydroxyasimicinone 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. Based on a literature review very few articles have been published on 9-Hydroxyasimicinone.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335202 (9-Hydroxyasimicinone)


  Mrv2104 05262303032D          

 45 47  0  0  0  0            999 V2000
   -6.2407    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2407    0.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9738    0.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2544   -0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2544   -1.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9379   -1.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1689    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6887    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0280   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4042   -2.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
Download

3D MOL for NP0335202 (9-Hydroxyasimicinone)

Download
3D SDF for NP0335202 (9-Hydroxyasimicinone)

  Mrv2104 05262303032D          

 45 47  0  0  0  0            999 V2000
   -6.2407    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9738    0.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2544   -0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2544   -1.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9379   -1.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1689    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9746    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6887    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183    1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -2.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -2.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2606   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4042   -2.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    2.8108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8061    2.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4576    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8718    3.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
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  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
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  9 23  1  0  0  0  0
 11 12  1  0  0  0  0
 11 34  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
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 17 18  1  0  0  0  0
 17 45  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 36  1  0  0  0  0
 22 39  1  0  0  0  0
 23 24  1  0  0  0  0
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 26 27  1  0  0  0  0
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 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
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 44  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0335202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCC(O)CCCCC1CC(CC(C)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1/C37H66O8/c1-3-4-5-6-7-8-9-12-19-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-13-10-11-16-29(39)17-14-15-18-30-26-28(25-27(2)38)37(42)43-30/h28-36,39-41H,3-26H2,1-2H3

> <INCHI_KEY>
NWVGCWARKGPJIT-UHFFFAOYNA-N

> <FORMULA>
C37H66O8

> <MOLECULAR_WEIGHT>
638.927

> <EXACT_MASS>
638.475769085

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
78.79366216549025

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{5,11-dihydroxy-11-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]undecyl}-3-(2-oxopropyl)oxolan-2-one

> <JCHEM_LOGP>
7.085332262

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.501148637067814

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.899093232206383

> <JCHEM_PKA_STRONGEST_BASIC>
-1.273797514373295

> <JCHEM_POLAR_SURFACE_AREA>
122.52

> <JCHEM_REFRACTIVITY>
176.21320000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-{5,11-dihydroxy-11-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]undecyl}-3-(2-oxopropyl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335202 (9-Hydroxyasimicinone)
Download
PDB for NP0335202 (9-Hydroxyasimicinone)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0     -11.649   2.468   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.649   0.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.188   0.448   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -9.284   1.696   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.188   2.936   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.188  -1.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.675  -1.498   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.675  -3.042   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.188  -3.602   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -9.217  -2.416   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.852   3.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.519   2.936   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.184   3.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.851   2.936   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.518   3.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.182   2.936   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.849   3.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.486   2.936   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.819   3.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.152   2.936   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.488   3.703   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.821   2.936   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.852  -4.369   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.519  -3.602   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.184  -4.369   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.851  -3.602   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.518  -4.369   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.182  -3.602   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.849  -4.369   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.486  -3.602   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.819  -4.369   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.152  -3.602   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.488  -4.369   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.852   5.247   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -8.852  -5.913   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.222   1.449   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.761   1.449   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.304   2.936   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.105   3.893   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.791   3.338   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.188   4.820   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.675   5.221   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.094   5.913   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.644   0.183   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -0.849   5.247   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4   11                                                  
CONECT    6    3    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    6    9                                                       
CONECT   11    5   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   45                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   36   39                                                  
CONECT   23    9   24   35                                                  
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                                                            
CONECT   34   11                                                            
CONECT   35   23                                                            
CONECT   36   22   37                                                       
CONECT   37   36   38   44                                                  
CONECT   38   37   39   40                                                  
CONECT   39   22   38                                                       
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   37                                                            
CONECT   45   17                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

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3D PDB for NP0335202 (9-Hydroxyasimicinone)
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SMILES for NP0335202 (9-Hydroxyasimicinone)
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCC(O)CCCCC1CC(CC(C)=O)C(=O)O1
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INCHI for NP0335202 (9-Hydroxyasimicinone)
InChI=1/C37H66O8/c1-3-4-5-6-7-8-9-12-19-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-13-10-11-16-29(39)17-14-15-18-30-26-28(25-27(2)38)37(42)43-30/h28-36,39-41H,3-26H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC37H66O8
Average Mass638.9270 Da
Monoisotopic Mass638.47577 Da
IUPAC Name5-{5,11-dihydroxy-11-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]undecyl}-3-(2-oxopropyl)oxolan-2-one
Traditional Name5-{5,11-dihydroxy-11-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]undecyl}-3-(2-oxopropyl)oxolan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCC(O)CCCCC1CC(CC(C)=O)C(=O)O1
InChI Identifier
InChI=1/C37H66O8/c1-3-4-5-6-7-8-9-12-19-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-13-10-11-16-29(39)17-14-15-18-30-26-28(25-27(2)38)37(42)43-30/h28-36,39-41H,3-26H2,1-2H3
InChI KeyNWVGCWARKGPJIT-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohols  
Direct ParentAnnonaceous acetogenins  
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
    • 

  • Long chain fatty alcohol
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.09ChemAxon
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity176.21 m³·mol⁻¹ChemAxon
Polarizability78.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available