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Showing NP-Card for 4-hydroxy-6-pentadecylpyran-2-one (NP0223707)

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Record Information
Version2.0
Created at2022-09-06 01:52:55 UTC
Updated at2022-09-06 01:52:55 UTC
NP-MRD IDNP0223707
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-6-pentadecylpyran-2-one
Description4-Hydroxy-6-pentadecylpyran-2-one, also known as palmitoyl triketide pyrone, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. 4-Hydroxy-6-pentadecylpyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-hydroxy-6-pentadecylpyran-2-one is found in Garcinia conrauana. A 2-pyranone in which the hydrogens at positions 4 and 6 of 2H-pyran-2-one are replaced by hydroxy and pentadecyl groups respectively.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)


  Mrv1533004241510382D          

 23 23  0  0  0  0            999 V2000
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
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3D MOL for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)

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3D SDF for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)

  Mrv1533004241510382D          

 23 23  0  0  0  0            999 V2000
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC1=CC(O)=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-18(21)17-20(22)23-19/h16-17,21H,2-15H2,1H3

> <INCHI_KEY>
YDVWWMILPXBXSV-UHFFFAOYSA-N

> <FORMULA>
C20H34O3

> <MOLECULAR_WEIGHT>
322.489

> <EXACT_MASS>
322.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.142244555002904

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-6-pentadecyl-2H-pyran-2-one

> <ALOGPS_LOGP>
7.35

> <JCHEM_LOGP>
6.850996689666667

> <ALOGPS_LOGS>
-5.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.90560501434259

> <JCHEM_PKA_STRONGEST_BASIC>
-5.901888366727946

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
98.14389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6-pentadecylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)
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PDB for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.674 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.007 -16.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.341 -16.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.341 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      28.007 -20.790   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      26.674 -18.480   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      30.675 -16.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    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   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16                                                       
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

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3D PDB for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)
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SMILES for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)
CCCCCCCCCCCCCCCC1=CC(O)=CC(=O)O1
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INCHI for NP0223707 (4-hydroxy-6-pentadecylpyran-2-one)
InChI=1S/C20H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-18(21)17-20(22)23-19/h16-17,21H,2-15H2,1H3
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View in JSmol
Synonyms
ValueSource
Palmitoyl triketide pyroneChEBI
Chemical FormulaC20H34O3
Average Mass322.4890 Da
Monoisotopic Mass322.25079 Da
IUPAC Name4-hydroxy-6-pentadecyl-2H-pyran-2-one
Traditional Name4-hydroxy-6-pentadecylpyran-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC1=CC(O)=CC(=O)O1
InChI Identifier
InChI=1S/C20H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-18(21)17-20(22)23-19/h16-17,21H,2-15H2,1H3
InChI KeyYDVWWMILPXBXSV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Garcinia conrauanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP7.35ALOGPS
logP6.85ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.14 m³·mol⁻¹ChemAxon
Polarizability41.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 ID84168  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]