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Showing NP-Card for 1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate (NP0308829)

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Record Information
Version2.0
Created at2022-09-11 02:55:29 UTC
Updated at2022-09-11 02:55:29 UTC
NP-MRD IDNP0308829
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate
Description15-Palmitoylsolamin, also known as 15-hexadecanoylsolamin, 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. 15-Palmitoylsolamin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 15-Palmitoylsolamin has been detected, but not quantified in, fruits. 1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate is found in Annona muricata. This could make 15-palmitoylsolamin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)


  Mrv0541 05061309042D          

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M  END
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3D MOL for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)

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3D SDF for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)

  Mrv0541 05061309042D          

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M  END
> <DATABASE_ID>
NP0308829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCC1=CC(C)OC1=O)C1CCC(O1)C(O)CCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C51H94O6/c1-4-6-8-10-12-14-16-17-18-24-28-32-36-40-50(53)57-48(39-35-31-27-23-20-19-21-25-29-33-37-45-43-44(3)55-51(45)54)49-42-41-47(56-49)46(52)38-34-30-26-22-15-13-11-9-7-5-2/h43-44,46-49,52H,4-42H2,1-3H3

> <INCHI_KEY>
GBSUIQLRRKMVMZ-UHFFFAOYSA-N

> <FORMULA>
C51H94O6

> <MOLECULAR_WEIGHT>
803.2885

> <EXACT_MASS>
802.70504074

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
107.55210274040742

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl hexadecanoate

> <ALOGPS_LOGP>
10.50

> <JCHEM_LOGP>
17.400745594333333

> <ALOGPS_LOGS>
-7.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.165146052700862

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.150301175822285

> <JCHEM_PKA_STRONGEST_BASIC>
-3.14866532662555

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
239.5956

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5H-furan-3-yl)tridecyl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)
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PDB for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)
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     -31.240 -13.019   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.628  -3.723   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.432 -18.523   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -29.705 -13.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.174  -4.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -28.828 -11.879   0.000  0.00  0.00           C+0
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HETATM    8  C   UNK     0     -27.293 -12.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.553  -3.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -26.416 -10.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.386  -2.731   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -24.881 -10.867   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.932  -3.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -24.004  -9.601   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.765  -2.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -22.470  -9.728   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -21.593  -8.462   0.000  0.00  0.00           C+0
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HETATM   19  C   UNK     0      -3.175  -9.981   0.000  0.00  0.00           C+0
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HETATM   23  C   UNK     0      -5.368  -8.462   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -19.181  -7.322   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.983 -11.500   0.000  0.00  0.00           C+0
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HETATM   27  C   UNK     0      -6.025  -7.069   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -17.646  -7.449   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.552 -11.626   0.000  0.00  0.00           C+0
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HETATM   34  C   UNK     0      -3.476  -1.243   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.218  -5.550   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -15.234  -6.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.745 -13.145   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.930  -1.752   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.753  -5.424   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.357  -5.044   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -8.817  -0.379   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.042  -1.312   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.663 -15.889   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.719 -17.010   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.403 -14.538   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -6.097  -0.747   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -7.551  -1.256   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -10.411  -4.031   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -9.533  -2.765   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -12.822  -5.170   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.916 -14.824   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -5.811   0.766   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -12.165  -6.563   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       6.037 -13.768   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       5.111 -16.352   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -7.994  -2.731   0.000  0.00  0.00           O+0
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CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   44                                                            
CONECT    4    1    6                                                       
CONECT    5    2    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   22                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   24                                                       
CONECT   19   20   21                                                       
CONECT   20   19   23                                                       
CONECT   21   19   25                                                       
CONECT   22   15   26                                                       
CONECT   23   20   27                                                       
CONECT   24   18   28                                                       
CONECT   25   21   29                                                       
CONECT   26   22   30                                                       
CONECT   27   23   31                                                       
CONECT   28   24   32                                                       
CONECT   29   25   33                                                       
CONECT   30   26   34                                                       
CONECT   31   27   35                                                       
CONECT   32   28   36                                                       
CONECT   33   29   37                                                       
CONECT   34   30   38                                                       
CONECT   35   31   39                                                       
CONECT   36   32   40                                                       
CONECT   37   33   45                                                       
CONECT   38   34   46                                                       
CONECT   39   35   48                                                       
CONECT   40   36   50                                                       
CONECT   41   42   47                                                       
CONECT   42   41   49                                                       
CONECT   43   44   45                                                       
CONECT   44    3   43   55                                                  
CONECT   45   37   43   51                                                  
CONECT   46   38   47   52                                                  
CONECT   47   41   46   56                                                  
CONECT   48   39   49   57                                                  
CONECT   49   42   48   56                                                  
CONECT   50   40   53   57                                                  
CONECT   51   45   54   55                                                  
CONECT   52   46                                                            
CONECT   53   50                                                            
CONECT   54   51                                                            
CONECT   55   44   51                                                       
CONECT   56   47   49                                                       
CONECT   57   48   50                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  116    0
END

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3D PDB for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)
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SMILES for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)
CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCC1=CC(C)OC1=O)C1CCC(O1)C(O)CCCCCCCCCCCC
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INCHI for NP0308829 (1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl hexadecanoate)
InChI=1S/C51H94O6/c1-4-6-8-10-12-14-16-17-18-24-28-32-36-40-50(53)57-48(39-35-31-27-23-20-19-21-25-29-33-37-45-43-44(3)55-51(45)54)49-42-41-47(56-49)46(52)38-34-30-26-22-15-13-11-9-7-5-2/h43-44,46-49,52H,4-42H2,1-3H3
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View in JSmol
Synonyms
ValueSource
15-HexadecanoylsolaminHMDB
1-[5-(1-Hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl hexadecanoic acidGenerator
Chemical FormulaC51H94O6
Average Mass803.2885 Da
Monoisotopic Mass802.70504 Da
IUPAC Name1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl hexadecanoate
Traditional Name1-[5-(1-hydroxytridecyl)oxolan-2-yl]-13-(5-methyl-2-oxo-5H-furan-3-yl)tridecyl hexadecanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCC1=CC(C)OC1=O)C1CCC(O1)C(O)CCCCCCCCCCCC
InChI Identifier
InChI=1S/C51H94O6/c1-4-6-8-10-12-14-16-17-18-24-28-32-36-40-50(53)57-48(39-35-31-27-23-20-19-21-25-29-33-37-45-43-44(3)55-51(45)54)49-42-41-47(56-49)46(52)38-34-30-26-22-15-13-11-9-7-5-2/h43-44,46-49,52H,4-42H2,1-3H3
InChI KeyGBSUIQLRRKMVMZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona muricataLOTUS Database
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
    • 

  • Fatty alcohol ester
    • 

  • Fatty acid ester
    • 

  • 2-furanone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Dihydrofuran
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • 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
logP10.5ALOGPS
logP17.4ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.15ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity239.6 m³·mol⁻¹ChemAxon
Polarizability107.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036341  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015212  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102506803  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]