Showing NP-Card for 18-Hydroxyoctadecanoic acid (NP0046996)

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Record Information
Version2.0
Created at2022-03-17 20:32:54 UTC
Updated at2022-03-17 20:32:54 UTC
NP-MRD IDNP0046996
Secondary Accession NumbersNone
Natural Product Identification
Common Name18-Hydroxyoctadecanoic acid
Description18-Hydroxyoctadecanoic acid, also known as omega-hydroxystearic acid or 18-hydroxystearate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. An omega-hydroxy-long-chain fatty acid that is octadecanoic (stearic) acid in which one of the hydrogens of the terminal methyl group has been replaced by a hydroxy group. 18-Hydroxyoctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 18-Hydroxyoctadecanoic acid has been detected, but not quantified in, gooseberries and potato. 18-Hydroxyoctadecanoic acid is found in Arabidopsis thaliana and Pinus radiata. 18-Hydroxyoctadecanoic acid was first documented in 2005 (PMID: 15846120). This could make 18-hydroxyoctadecanoic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046996 (18-Hydroxyoctadecanoic acid)

  Mrv1652310091719302D          

 21 20  0  0  0  0            999 V2000
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
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3D MOL for NP0046996 (18-Hydroxyoctadecanoic acid)

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3D SDF for NP0046996 (18-Hydroxyoctadecanoic acid)
  Mrv1652310091719302D          

 21 20  0  0  0  0            999 V2000
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCCCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h19H,1-17H2,(H,20,21)

> <INCHI_KEY>
VLHZUYUOEGBBJB-UHFFFAOYSA-N

> <FORMULA>
C18H36O3

> <MOLECULAR_WEIGHT>
300.483

> <EXACT_MASS>
300.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.678720878310266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-hydroxyoctadecanoic acid

> <ALOGPS_LOGP>
6.78

> <JCHEM_LOGP>
5.709041491

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.84394282199214

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019704603348

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922594590354228

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
88.21429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-hydroxy stearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046996 (18-Hydroxyoctadecanoic acid)
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PDB for NP0046996 (18-Hydroxyoctadecanoic acid)
HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0      12.209  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.876   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.543   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.542  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.877  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.210   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.544  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.878   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.212  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.545   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.879  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      24.213   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    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   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

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3D PDB for NP0046996 (18-Hydroxyoctadecanoic acid)
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SMILES for NP0046996 (18-Hydroxyoctadecanoic acid)
OCCCCCCCCCCCCCCCCCC(O)=O
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INCHI for NP0046996 (18-Hydroxyoctadecanoic acid)
InChI=1S/C18H36O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h19H,1-17H2,(H,20,21)
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View in JSmol
Synonyms
ValueSource
18-Hydroxystearic acidChEBI
Omega-hydroxyoctadecanoic acidChEBI
Omega-hydroxystearic acidChEBI
18-HydroxystearateGenerator
Omega-hydroxyoctadecanoateGenerator
Omega-hydroxystearateGenerator
18-HydroxyoctadecanoateGenerator
Chemical FormulaC18H36O3
Average Mass300.4830 Da
Monoisotopic Mass300.26645 Da
IUPAC Name18-hydroxyoctadecanoic acid
Traditional Name18-hydroxy stearic acid
CAS Registry NumberNot Available
SMILES
OCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H36O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h19H,1-17H2,(H,20,21)
InChI KeyVLHZUYUOEGBBJB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
Pinus radiataLOTUS Database
Ribes uva-crispaFooDB
Solanum tuberosumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentLong-chain fatty acids  
Alternative Parents
Substituents
  • Long-chain fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP6.78ALOGPS
logP5.71ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity88.21 m³·mol⁻¹ChemAxon
Polarizability39.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0171069  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006898  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282915  
PDB IDNot Available
ChEBI ID79182  
Good Scents IDNot Available
References
General References
  1. Abe A, Sugiyama K: Growth inhibition and apoptosis induction of human melanoma cells by omega-hydroxy fatty acids. Anticancer Drugs. 2005 Jun;16(5):543-9. doi: 10.1097/00001813-200506000-00010. [PubMed:15846120  ]