MiMeDB: Showing metabocard for (9Z)-12-hydroxyoctadec-9-enoic acid (MMDBc0050825)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 20:07:39 UTC

Update Date

2024-04-30 20:42:45 UTC

Metabolite ID

MMDBc0050825

Metabolite Identification

Common Name

(9Z)-12-hydroxyoctadec-9-enoic acid

Description

Ricinoleic 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. Based on a literature review a significant number of articles have been published on Ricinoleic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0034297
     RDKit          3D
Ricinoleic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.5887    0.8820    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.3081    0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8339   -0.0321    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053   -0.6884    2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874   -0.0837    2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -0.0093    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    0.5958    0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.2012    1.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.6464   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -0.7040   -1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2365   -2.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -0.5834   -2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.3440   -1.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035   -0.5456   -1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.2107   -1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -0.4004   -1.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.9914   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.0357    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176    0.4149    1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6553   -0.1007    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044    0.3879    2.7293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6046    1.8517    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1806    0.1419    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8405    0.9294   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.4556   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642    1.2148    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7337   -0.6616    2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0384    0.9254    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899   -1.0692    3.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5748   -1.6883    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582    0.9480    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -0.6996    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045    0.5371    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877   -1.0906    0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.6084    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456   -1.1183    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    1.2440   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322    1.2663   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -1.2566   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -2.2678   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -0.6398   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    0.4533   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113   -2.3794   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -1.3762   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.3989   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.4312   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.1985   -1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -1.3750   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310   -0.9107   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9113   -0.3145   -2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095    1.5338   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9498    1.5860   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.0769    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887    0.5052    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -0.5220    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
M  END


  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>
MMDBc0050825

> <DATABASE_NAME>
MIME

> <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

$$$$

HMDB0034297
     RDKit          3D
Ricinoleic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.5887    0.8820    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.3081    0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8339   -0.0321    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053   -0.6884    2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874   -0.0837    2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -0.0093    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    0.5958    0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.2012    1.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.6464   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -0.7040   -1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2365   -2.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -0.5834   -2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.3440   -1.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035   -0.5456   -1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.2107   -1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -0.4004   -1.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.9914   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.0357    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176    0.4149    1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6553   -0.1007    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044    0.3879    2.7293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6046    1.8517    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1806    0.1419    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8405    0.9294   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.4556   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642    1.2148    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7337   -0.6616    2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0384    0.9254    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899   -1.0692    3.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5748   -1.6883    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582    0.9480    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -0.6996    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045    0.5371    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877   -1.0906    0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.6084    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456   -1.1183    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    1.2440   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322    1.2663   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -1.2566   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -2.2678   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -0.6398   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    0.4533   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113   -2.3794   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -1.3762   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.3989   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.4312   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.1985   -1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -1.3750   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310   -0.9107   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9113   -0.3145   -2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095    1.5338   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9498    1.5860   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.0769    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887    0.5052    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -0.5220    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
M  END

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

COMPND    HMDB0034297
HETATM    1  C1  UNL     1      -7.589   0.882   0.531  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.123   0.308   0.595  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.834  -0.032   1.997  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.605  -0.688   2.421  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.287  -0.084   2.178  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.917  -0.009   0.747  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.540   0.596   0.531  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.603  -0.201   1.170  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.278   0.646  -0.953  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.314  -0.704  -1.525  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.280  -1.237  -2.114  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.004  -0.583  -2.275  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.143  -1.344  -1.603  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.404  -0.546  -1.856  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.608  -1.211  -1.227  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.847  -0.400  -1.491  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.738   0.991  -0.923  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.528   1.036   0.551  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.618   0.415   1.337  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.655  -0.101   0.862  1.00  0.00           O  
HETATM   21  O3  UNL     1       6.504   0.388   2.729  1.00  0.00           O  
HETATM   22  H1  UNL     1      -7.605   1.852   1.034  1.00  0.00           H  
HETATM   23  H2  UNL     1      -8.181   0.142   1.088  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.841   0.929  -0.547  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.087  -0.456  -0.159  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.564   1.215   0.196  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.734  -0.662   2.366  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.038   0.925   2.615  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.690  -1.069   3.502  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.575  -1.688   1.825  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.258   0.948   2.649  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.514  -0.700   2.749  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.604   0.537   0.152  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.788  -1.091   0.416  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.469   1.608   0.995  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.946  -1.118   1.353  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.387   1.244  -1.167  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.132   1.266  -1.413  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.262  -1.257  -1.453  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.384  -2.268  -2.526  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.250  -0.640  -3.388  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.121   0.453  -2.021  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.211  -2.379  -1.987  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.957  -1.376  -0.517  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.516  -0.399  -2.936  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.272   0.431  -1.333  1.00  0.00           H  
HETATM   47  H26 UNL     1       4.729  -2.198  -1.714  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.439  -1.375  -0.157  1.00  0.00           H  
HETATM   49  H28 UNL     1       6.731  -0.911  -1.091  1.00  0.00           H  
HETATM   50  H29 UNL     1       5.911  -0.314  -2.614  1.00  0.00           H  
HETATM   51  H30 UNL     1       6.709   1.534  -1.123  1.00  0.00           H  
HETATM   52  H31 UNL     1       4.950   1.586  -1.423  1.00  0.00           H  
HETATM   53  H32 UNL     1       5.424   2.077   0.917  1.00  0.00           H  
HETATM   54  H33 UNL     1       4.589   0.505   0.864  1.00  0.00           H  
HETATM   55  H34 UNL     1       6.570  -0.522   3.164  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    9   35
CONECT    8   36
CONECT    9   10   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   20   21
CONECT   21   55
END

HMDB0034297
     RDKit          3D
Ricinoleic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.5887    0.8820    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.3081    0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8339   -0.0321    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053   -0.6884    2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874   -0.0837    2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -0.0093    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    0.5958    0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.2012    1.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.6464   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -0.7040   -1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2365   -2.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -0.5834   -2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.3440   -1.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035   -0.5456   -1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.2107   -1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -0.4004   -1.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.9914   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.0357    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176    0.4149    1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6553   -0.1007    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044    0.3879    2.7293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6046    1.8517    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1806    0.1419    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8405    0.9294   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.4556   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642    1.2148    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7337   -0.6616    2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0384    0.9254    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899   -1.0692    3.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5748   -1.6883    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582    0.9480    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -0.6996    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045    0.5371    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877   -1.0906    0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.6084    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456   -1.1183    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    1.2440   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322    1.2663   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -1.2566   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -2.2678   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -0.6398   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    0.4533   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113   -2.3794   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -1.3762   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.3989   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.4312   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.1985   -1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -1.3750   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310   -0.9107   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9113   -0.3145   -2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095    1.5338   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9498    1.5860   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.0769    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887    0.5052    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -0.5220    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
M  END

Synonyms

Value	Source
12-Hydroxyoleic acid	ChEBI
12-Hydroxyoleate	Generator
Ricinoleate	Generator
(9Z)-(12S)-Hydroxyoctadecenoic acid	HMDB
(9Z)-12-Hydroxy-9-octadecenoic acid	HMDB
(9Z)-12-Hydroxyoctadec-9-enoic acid	HMDB
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid	HMDB
(R)-12-Hydroxy-cis-9-octadecenoic acid	HMDB
12-Hydroxy-(9Z,12R)-9-octadecenoic acid	HMDB
12-Hydroxy-9-octadecenoic acid	HMDB, MeSH
12-Hydroxy-cis-9-octadecenoic acid	HMDB
12-Hydroxy-oleic acid	HMDB
12-Hydroxy-[R-(Z)]-9-octadecenoic acid	HMDB
D-12-Hydroxyoleic acid	HMDB
Flexricin 100	HMDB
L'acide ricinoleique	HMDB
P -10 acid	HMDB
RCL	HMDB
Ricinelaidic acid	HMDB, MeSH
Ricinic acid	HMDB
Ricinolic acid	HMDB
Ricinusoleic acid	HMDB
Riconoleic acid	HMDB
12-Hydroxy-9-octadecenic acid	MeSH, HMDB
12-Hydroxyoctadec-cis-9-enoic acid	MeSH, HMDB
Ricinoleic acid, (R-(e))-isomer	MeSH, HMDB
(9Z)-12-Hydroxyoctadec-9-enoate	Generator
12-D-Hydroxy-9-trans-octadecenoic acid	MeSH
Ricinoleic acid	MeSH

Molecular Formula

C₁₈H₃₄O₃

Average Mass

298.4608

Monoisotopic Mass

298.250794954

IUPAC Name

(9Z)-12-hydroxyoctadec-9-enoic acid

Traditional Name

12-hydroxy-oleic acid

CAS Registry Number

Not Available

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-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 Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:85639 )
monounsaturated fatty acid (CHEBI:85639 )
hydroxy fatty acid (CHEBI:85639 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
logP	6.14	ALOGPS
logP	5.4	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	89.07 m³·mol⁻¹	ChemAxon
Polarizability	37.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6950000000-bd57542588f0c1f373c9	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00bi-9341100000-50290e07e9579df3d010	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-b7d5b714e0c3125f33e7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01wr-5390000000-803f620a2725a28437e3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9410000000-69dc43fc42f33c85490a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-81b1052b32aa5dea7caa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-1090000000-882e590b68505336b690	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9520000000-d6043d034d45f5c3c900	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-73c92bc92640dda69d13	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0190000000-dd9b67fa784fafec469a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9350000000-f54f3e16cea0f73fc3c7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0290000000-2e109924cba4f0fc25a6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-7950000000-b0d44074bb01991c64e0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9300000000-5d488b145dc0c6c88b83	2021-09-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces
Eukaryota/Fungi	Basidiomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620

External Links

HMDB ID

HMDB0034297

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ricinoleic acid

METLIN ID

Not Available

PubChem Compound

5282942

PDB ID

Not Available

ChEBI ID

85639

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (9Z)-12-hydroxyoctadec-9-enoic acid (MMDBc0050825)

MOL for #<Metabolite:0x00005634c2cbf398>

3D MOL for #<Metabolite:0x00005634c2cbf398>

3D SDF for #<Metabolite:0x00005634c2cbf398>

3D-SDF for #<Metabolite:0x00005634c2cbf398>

PDB for #<Metabolite:0x00005634c2cbf398>

3D PDB for #<Metabolite:0x00005634c2cbf398>

SMILES for #<Metabolite:0x00005634c2cbf398>

INCHI for #<Metabolite:0x00005634c2cbf398>

Structure for #<Metabolite:0x00005634c2cbf398>

3D Structure for #<Metabolite:0x00005634c2cbf398>