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Showing NP-Card for 16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate (NP0255240)

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Record Information
Version2.0
Created at2022-09-07 19:39:48 UTC
Updated at2022-09-07 19:39:48 UTC
NP-MRD IDNP0255240
Secondary Accession NumbersNone
Natural Product Identification
Common Name16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate
Description16-(Acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. 16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate is found in Cussonia zimmermannii. 16-(Acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)


  Mrv1533004241512422D          

 27 26  0  0  0  0            999 V2000
    6.7105   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2855   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7144   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
 15 17  1  0  0  0  0
 17 18  3  0  0  0  0
 18 19  1  0  0  0  0
 19 20  3  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
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3D MOL for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)

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3D SDF for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)

  Mrv1533004241512422D          

 27 26  0  0  0  0            999 V2000
    6.7105   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2855   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7144   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
 15 17  1  0  0  0  0
 17 18  3  0  0  0  0
 18 19  1  0  0  0  0
 19 20  3  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0255240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCCCCCCCCCCC(O)C#CC#CC(OC(C)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-4-22(27-20(3)24)17-13-12-16-21(25)15-11-9-7-5-6-8-10-14-18-26-19(2)23/h4,21-22,25H,1,5-11,14-15,18H2,2-3H3

> <INCHI_KEY>
AVKOLTWNMGUSAT-UHFFFAOYSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.75636769977076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.471244745666667

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.324740702338367

> <JCHEM_PKA_STRONGEST_BASIC>
-3.094158416797197

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
106.49579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)
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PDB for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)
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      12.526  -8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860  -8.002   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.860  -6.462   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.194  -8.772   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.527  -8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.861  -8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.195  -8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.528  -8.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.862  -8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.196  -8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.529  -8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.863  -8.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.197  -8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.530  -8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.864  -8.002   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      29.864  -6.462   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      31.198  -8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.532  -9.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.865 -10.312   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.199 -11.082   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.533 -11.852   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      37.866 -11.082   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      39.200 -11.852   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      40.534 -11.082   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      39.200 -13.392   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.533 -13.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.199 -14.162   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

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3D PDB for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)
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SMILES for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)
CC(=O)OCCCCCCCCCCC(O)C#CC#CC(OC(C)=O)C=C
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INCHI for NP0255240 (16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate)
InChI=1S/C22H32O5/c1-4-22(27-20(3)24)17-13-12-16-21(25)15-11-9-7-5-6-8-10-14-18-26-19(2)23/h4,21-22,25H,1,5-11,14-15,18H2,2-3H3
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Synonyms
ValueSource
16-(Acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetic acidGenerator
Chemical FormulaC22H32O5
Average Mass376.4930 Da
Monoisotopic Mass376.22497 Da
IUPAC Name16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate
Traditional Name16-(acetyloxy)-11-hydroxyoctadec-17-en-12,14-diyn-1-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCCCCCCCCCCC(O)C#CC#CC(OC(C)=O)C=C
InChI Identifier
InChI=1S/C22H32O5/c1-4-22(27-20(3)24)17-13-12-16-21(25)15-11-9-7-5-6-8-10-14-18-26-19(2)23/h4,21-22,25H,1,5-11,14-15,18H2,2-3H3
InChI KeyAVKOLTWNMGUSAT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cussonia zimmermanniiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohol esters  
Direct ParentFatty alcohol esters  
Alternative Parents
Substituents
  • Fatty alcohol ester
    • 

  • Fatty alcohol
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP5.04ALOGPS
logP4.47ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity106.5 m³·mol⁻¹ChemAxon
Polarizability45.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 Compound11632231  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]