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Showing NP-Card for Ricinoleic acid (NP0047929)

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Record Information
Version2.0
Created at2022-03-17 20:48:15 UTC
Updated at2022-03-17 20:48:15 UTC
NP-MRD IDNP0047929
Secondary Accession NumbersNone
Natural Product Identification
Common NameRicinoleic acid
DescriptionRicinoleic acid, also known as 12-hydroxyoleate or ricinoleate, 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. Ricinoleic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ricinoleic acid has been detected, but not quantified in, a few different foods, such as corns, fats and oils, and fruits. This could make ricinoleic acid a potential biomarker for the consumption of these foods. Ricinoleic acid is found in Artocarpus integer, Azima tetracantha, Brunfelsia americana, Cephalocroton cordofanus, Claviceps purpurea , Cordia sinensis, Crotalaria pallida, Crotalaria retusa, Ganoderma lucidum , Hevea brasiliensis, Lesquerella densipila, Linum mucronatum, Platycodon grandiflorus, Ricinus communis , Ricinus opp. and Trichodesma zeylanicum. Ricinoleic acid was first documented in 1982 (PMID: 6948953). A hydroxy fatty acid that is (9Z)-octadec-9-enoic (oleic) acid carrying a hydroxy substituent at position 12 (PMID: 11050297).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047929 (Ricinoleic acid)


  Mrv0541 05061307422D          

 21 20  0  0  0  0            999 V2000
    9.4875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.0000    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
    5.7750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  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  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 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 NP0047929 (Ricinoleic acid)

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3D SDF for NP0047929 (Ricinoleic acid)

  Mrv0541 05061307422D          

 21 20  0  0  0  0            999 V2000
    9.4875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.0000    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
    5.7750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  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  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 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>
NP0047929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-

> <INCHI_KEY>
WBHHMMIMDMUBKC-XFXZXTDPSA-N

> <FORMULA>
C18H34O3

> <MOLECULAR_WEIGHT>
298.4608

> <EXACT_MASS>
298.250794954

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.85424145779921

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z)-12-hydroxyoctadec-9-enoic acid

> <ALOGPS_LOGP>
6.14

> <JCHEM_LOGP>
5.397079924

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.401256348683585

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167501938923

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3110906911209161

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
89.07169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-oleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047929 (Ricinoleic acid)
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PDB for NP0047929 (Ricinoleic acid)
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      17.710   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.170   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.400   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.090   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.240   0.000   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      10.780   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.550  -1.334   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3   11                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   13                                                       
CONECT   11    4   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   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 NP0047929 (Ricinoleic acid)
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SMILES for NP0047929 (Ricinoleic acid)
CCCCCCC(O)C\C=C/CCCCCCCC(O)=O
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INCHI for NP0047929 (Ricinoleic acid)
InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-
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Synonyms
ValueSource
12-Hydroxyoleic acidChEBI
12-HydroxyoleateGenerator
RicinoleateGenerator
(9Z)-(12S)-Hydroxyoctadecenoic acidHMDB
(9Z)-12-Hydroxy-9-octadecenoic acidHMDB
(9Z)-12-Hydroxyoctadec-9-enoic acidHMDB
(9Z,12R)-12-Hydroxyoctadec-9-enoic acidHMDB
(R)-12-Hydroxy-cis-9-octadecenoic acidHMDB
12-Hydroxy-(9Z,12R)-9-octadecenoic acidHMDB
12-Hydroxy-9-octadecenoic acidHMDB
12-Hydroxy-cis-9-octadecenoic acidHMDB
12-Hydroxy-oleic acidHMDB
12-Hydroxy-[R-(Z)]-9-octadecenoic acidHMDB
D-12-Hydroxyoleic acidHMDB
Flexricin 100HMDB
L'acide ricinoleiqueHMDB
p -10 acidHMDB
RCLHMDB
Ricinelaidic acidHMDB
Ricinic acidHMDB
Ricinolic acidHMDB
Ricinusoleic acidHMDB
Riconoleic acidHMDB
12-Hydroxy-9-octadecenic acidHMDB
12-Hydroxyoctadec-cis-9-enoic acidHMDB
Ricinoleic acid, (R-(e))-isomerHMDB
(9Z)-12-Hydroxyoctadec-9-enoateGenerator
12-D-Hydroxy-9-trans-octadecenoic acidMeSH
Ricinoleic acidMeSH
Chemical FormulaC18H34O3
Average Mass298.4608 Da
Monoisotopic Mass298.25079 Da
IUPAC Name(9Z)-12-hydroxyoctadec-9-enoic acid
Traditional Name12-hydroxy-oleic acid
CAS Registry Number141-22-0
SMILES
CCCCCCC(O)C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-
InChI KeyWBHHMMIMDMUBKC-XFXZXTDPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artocarpus champedenLOTUS Database
Azima tetracanthaLOTUS Database
Brunfelsia americanaLOTUS Database
Cephalocroton cordofanusLOTUS Database
Claviceps purpureaFungi
Cordia sinensisLOTUS Database
Crotalaria pallidaLOTUS Database
Crotalaria retusaLOTUS Database
Ganoderma lucidumFungi
Hevea brasiliensisLOTUS Database
Lesquerella densipilaPlant
Linum mucronatumLOTUS Database
Platycodon grandiflorusLOTUS Database
Ricinus communisPlant
Ricinus opp.Plant
Trichodesma zeylanicumLOTUS Database
Zea mays L.FooDB
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
    • 

  • Unsaturated fatty acid
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP6.14ALOGPS
logP5.4ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability37.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034297  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012640  
KNApSAcK IDC00001237  
Chemspider ID4446069  
KEGG Compound IDC08365  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRicinoleic acid  
METLIN IDNot Available
PubChem Compound5282942  
PDB IDNot Available
ChEBI ID85639  
Good Scents IDNot Available
References
General References
  1. Gullikson GW, Sender M, Bass P: Laxative-like effects of nonsteroidal anti-inflammatory drugs on intestinal fluid movement and membrane integrity. J Pharmacol Exp Ther. 1982 Feb;220(2):236-42. [PubMed:6948953  ] 
  2. Vieira C, Evangelista S, Cirillo R, Terracciano R, Lippi A, Maggi CA, Manzini S: Antinociceptive activity of ricinoleic acid, a capsaicin-like compound devoid of pungent properties. Eur J Pharmacol. 2000 Oct 27;407(1-2):109-16. doi: 10.1016/s0014-2999(00)00727-5. [PubMed:11050297  ]