Np mrd loader

Showing NP-Card for Asimicin (NP0049213)

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Record Information
Version1.0
Created at2022-03-17 21:08:53 UTC
Updated at2022-03-17 21:08:54 UTC
NP-MRD IDNP0049213
Secondary Accession NumbersNone
Natural Product Identification
Common NameAsimicin
DescriptionTrilobacin 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. Trilobacin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Trilobacin has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, fruits, and sugar apples. Asimicin is found in Annona atemoya , Annona cherimolia, Annona purpurea , Annona reticulata , Annona senegalensis, Asimina parviflora, Asimina triloba , Eurytides marcellus and Rollinia mucosa . It was first documented in 2000 (PMID: 11413487). This could make trilobacin a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049213 (Asimicin)


  Mrv0541 02241216212D          

 44 46  0  0  0  0            999 V2000
   -1.6920    4.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    3.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for NP0049213 (Asimicin)

Download
3D SDF for NP0049213 (Asimicin)

  Mrv0541 02241216212D          

 44 46  0  0  0  0            999 V2000
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    4.9928   -3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -4.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323   -4.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -4.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9291   -4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865   -4.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043   -3.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3617   -3.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5369   -2.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3423    3.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0049213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3

> <INCHI_KEY>
MBABCNBNDNGODA-UHFFFAOYSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
78.19038170351644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
6.98

> <JCHEM_LOGP>
8.682191933333334

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.379912503383732

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.851679326137901

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174217

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
176.39659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049213 (Asimicin)
Download
PDB for NP0049213 (Asimicin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.158   8.164   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.003   6.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.081   5.545   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.469   5.853   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.547   4.775   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.933   5.545   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.320   4.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.087  -4.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.087  -5.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.320  -6.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.320  -8.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.087  -8.781   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.701  -8.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.468  -9.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.081  -8.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.928  -6.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.542  -6.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.388  -4.775   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.002  -4.159   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.464   6.316   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.384   7.395   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.156   7.086   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.080   8.319   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.620   8.011   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.698   9.089   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.239   8.781   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.701   7.395   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.622   6.161   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.084   4.775   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.006   3.542   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.620   3.851   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.545   0.925   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.468  -0.307   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.009   0.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.009   1.694   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.468   2.156   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.006  -1.848   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.620  -2.310   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.620  -3.851   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.006  -4.312   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.931  -3.081   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.622   8.627   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.239   7.240   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -7.780   7.086   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   43                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   44                                                  
CONECT    7    6                                                            
CONECT    8    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   39                                                  
CONECT   19   18                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
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   36                                                  
CONECT   31   30                                                            
CONECT   32   33   36                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   30   32   35                                                  
CONECT   37   33   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   18   38   40                                                  
CONECT   40   39   41                                                       
CONECT   41   37   40                                                       
CONECT   42   43                                                            
CONECT   43    4   42   44                                                  
CONECT   44    6   43                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

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3D PDB for NP0049213 (Asimicin)
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SMILES for NP0049213 (Asimicin)
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O
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INCHI for NP0049213 (Asimicin)
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC37H66O7
Average Mass622.9157 Da
Monoisotopic Mass622.48085 Da
IUPAC Name3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one
Traditional Name3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-5H-furan-2-one
CAS Registry Number120298-30-8
SMILES
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3
InChI KeyMBABCNBNDNGODA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona atemoyaPlant
Annona cherimoliaPlant
Annona purpureaPlant
Annona reticulataPlant
Annona senegalensisLOTUS Database
Annona squamosaFooDB
Asimina parvifloraLOTUS Database
Asimina trilobaPlant
Eurytides marcellusAnimalia
Rollinia mucosaPlant
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.
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
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP6.98ALOGPS
logP8.68ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity176.4 m³·mol⁻¹ChemAxon
Polarizability78.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0031369  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018174  
KNApSAcK IDNot Available
Chemspider ID115108  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound130056  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. 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  ] 
  3. 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  ] 
  4. 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  ]