Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:33:28 UTC

Update Date

2021-09-23 16:33:28 UTC

HMDB ID

HMDB0302281

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9,10-Dihydroxystearic acid

Description

9,10-dihydroxystearic acid, also known as 9,10-dhsa or 9,10-dioh 18:0, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 9,10-dihydroxystearic acid is considered to be an octadecanoid lipid molecule. 9,10-dihydroxystearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9,10-dihydroxystearic acid can be found in peanut, which makes 9,10-dihydroxystearic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302281
     RDKit          3D
9,10-Dihydroxystearic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.9270   -0.4960    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9904   -1.3289   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7471   -1.7393    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9431   -0.5547    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    0.3210   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6987    1.4778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776    1.1241    1.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4129    0.3642    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.1047   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3155   -1.7823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.2314   -1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2734    0.8887   -2.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243    0.1320   -1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -0.3508    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.4771    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969    0.8166    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.6131    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -0.3577   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965   -0.6120   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9919   -1.1520    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.4151    1.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424   -1.4051    1.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950    0.5747    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -0.6894    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928   -0.6585    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7592   -0.8455   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5386   -2.2625   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0750   -2.2923    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1736   -2.4191   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856    0.0000    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271   -0.9680    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.2685   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4184    0.7486   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    1.9703    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    2.2778   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.5419    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    2.0745    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.1739    1.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -0.6469   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    2.0545   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.1713   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.7460   -1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874    1.7677   -2.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    1.1068   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135   -0.5878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.4353    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3384    0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -0.8035    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679   -1.2569   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    1.3471   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841    1.5079    0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.5909    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494    0.2597    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9142    0.0008   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418   -1.3686   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437    0.3631   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.2809   -1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0810   -1.0345    0.4945 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END


  Mrv1533004161506232D          

 22 21  0  0  0  0            999 V2000
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
M  END
> <DATABASE_ID>
HMDB0302281

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC(O)C(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)

> <INCHI_KEY>
VACHUYIREGFMSP-UHFFFAOYSA-N

> <FORMULA>
C18H36O4

> <MOLECULAR_WEIGHT>
316.482

> <EXACT_MASS>
316.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.78884256408016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dihydroxyoctadecanoic acid

> <ALOGPS_LOGP>
5.27

> <JCHEM_LOGP>
4.684097973666667

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.909717016038154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325350944831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440192571762076

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
89.3166

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxystearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302281
     RDKit          3D
9,10-Dihydroxystearic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.9270   -0.4960    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9904   -1.3289   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7471   -1.7393    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9431   -0.5547    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    0.3210   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6987    1.4778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776    1.1241    1.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4129    0.3642    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.1047   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3155   -1.7823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.2314   -1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2734    0.8887   -2.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243    0.1320   -1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -0.3508    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.4771    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969    0.8166    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.6131    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -0.3577   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965   -0.6120   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9919   -1.1520    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.4151    1.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424   -1.4051    1.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950    0.5747    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -0.6894    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928   -0.6585    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7592   -0.8455   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5386   -2.2625   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0750   -2.2923    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1736   -2.4191   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856    0.0000    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271   -0.9680    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.2685   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4184    0.7486   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    1.9703    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    2.2778   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.5419    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    2.0745    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.1739    1.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -0.6469   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    2.0545   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.1713   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.7460   -1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874    1.7677   -2.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    1.1068   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135   -0.5878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.4353    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3384    0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -0.8035    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679   -1.2569   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    1.3471   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841    1.5079    0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.5909    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494    0.2597    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9142    0.0008   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418   -1.3686   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437    0.3631   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.2809   -1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0810   -1.0345    0.4945 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.816  12.979   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      39.819   9.129   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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0302281
HETATM    1  C1  UNL     1      -7.927  -0.496   0.487  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.990  -1.329  -0.361  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.747  -1.739   0.386  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.943  -0.555   0.865  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.489   0.321  -0.284  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.699   1.478   0.249  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.478   1.124   1.004  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.413   0.364   0.308  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.815   1.105  -0.899  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.923   1.315  -1.782  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.110   0.231  -1.683  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.273   0.889  -2.990  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.524   0.132  -1.242  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.854  -0.351   0.104  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.386  -0.477   0.308  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.097   0.817   0.146  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.573   0.613   0.386  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.119  -0.358  -0.590  1.00  0.00           C  
HETATM   19  C17 UNL     1       7.597  -0.612  -0.442  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.992  -1.152   0.856  1.00  0.00           C  
HETATM   21  O3  UNL     1       7.225  -1.415   1.817  1.00  0.00           O  
HETATM   22  O4  UNL     1       9.342  -1.405   1.064  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.695   0.575   0.273  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.984  -0.689   0.236  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.793  -0.659   1.555  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.759  -0.846  -1.333  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.539  -2.262  -0.609  1.00  0.00           H  
HETATM   28  H6  UNL     1      -6.075  -2.292   1.291  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.174  -2.419  -0.241  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.486   0.000   1.633  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.027  -0.968   1.337  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.006  -0.268  -1.069  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.418   0.749  -0.741  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.390   1.970   1.010  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.584   2.278  -0.517  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.782   0.542   1.899  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.024   2.074   1.369  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.611   0.174   1.018  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.742  -0.647  -0.040  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.386   2.055  -0.673  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.827   2.171  -2.238  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.320  -0.746  -1.950  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.687   1.768  -2.720  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.050   1.107  -1.498  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.014  -0.588  -1.979  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.520   0.435   0.842  1.00  0.00           H  
HETATM   47  H25 UNL     1       1.435  -1.338   0.298  1.00  0.00           H  
HETATM   48  H26 UNL     1       3.499  -0.803   1.361  1.00  0.00           H  
HETATM   49  H27 UNL     1       3.668  -1.257  -0.431  1.00  0.00           H  
HETATM   50  H28 UNL     1       3.907   1.347  -0.812  1.00  0.00           H  
HETATM   51  H29 UNL     1       3.684   1.508   0.941  1.00  0.00           H  
HETATM   52  H30 UNL     1       6.083   1.591   0.257  1.00  0.00           H  
HETATM   53  H31 UNL     1       5.649   0.260   1.453  1.00  0.00           H  
HETATM   54  H32 UNL     1       5.914   0.001  -1.612  1.00  0.00           H  
HETATM   55  H33 UNL     1       5.642  -1.369  -0.434  1.00  0.00           H  
HETATM   56  H34 UNL     1       8.144   0.363  -0.587  1.00  0.00           H  
HETATM   57  H35 UNL     1       7.976  -1.281  -1.240  1.00  0.00           H  
HETATM   58  H36 UNL     1      10.081  -1.035   0.494  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   21   22
CONECT   22   58
END

HMDB0302281
     RDKit          3D
9,10-Dihydroxystearic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.9270   -0.4960    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9904   -1.3289   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7471   -1.7393    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9431   -0.5547    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    0.3210   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6987    1.4778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776    1.1241    1.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4129    0.3642    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.1047   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3155   -1.7823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.2314   -1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2734    0.8887   -2.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243    0.1320   -1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -0.3508    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.4771    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969    0.8166    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.6131    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -0.3577   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965   -0.6120   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9919   -1.1520    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.4151    1.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424   -1.4051    1.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950    0.5747    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -0.6894    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928   -0.6585    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7592   -0.8455   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5386   -2.2625   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0750   -2.2923    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1736   -2.4191   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856    0.0000    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271   -0.9680    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.2685   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4184    0.7486   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    1.9703    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    2.2778   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.5419    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    2.0745    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.1739    1.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -0.6469   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    2.0545   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.1713   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.7460   -1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874    1.7677   -2.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    1.1068   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135   -0.5878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.4353    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3384    0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -0.8035    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679   -1.2569   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    1.3471   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841    1.5079    0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.5909    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494    0.2597    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9142    0.0008   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418   -1.3686   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437    0.3631   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.2809   -1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0810   -1.0345    0.4945 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,10-DHSA	ChEBI
9,10-Dihydroxystearic acid	ChEBI
9,10-Dihydroxystearinsaeure	ChEBI
9,10-DiOH 18:0	ChEBI
9,10-DiOH C18:0	ChEBI
DHSA	ChEBI
Dioxystearinsaeure	ChEBI
9,10-Dihydroxystearate	Generator
9,10-Dihydroxyoctadecanoate	Generator
9,10-Dihydroxystearic acid, ammonium salt	MeSH
9,10-Dihydroxystearic acid, magnesium salt	MeSH
9,10-Dihydroxystearic acid, monocalcium salt	MeSH
9,10-Dihydroxystearic acid, sodium salt	MeSH
9,10-Dihydroxystearic acid, (r,s)-isomer	MeSH
9,10-Dihydroxystearic acid, potassium salt	MeSH
9,10-Dihydroxystearic acid, (r,r)-isomer	MeSH
9,10-Dihydroxystearic acid, dicalcium salt	MeSH
9,10-Dihydroxystearic acid, lithium salt	MeSH

Chemical Formula

C₁₈H₃₆O₄

Average Molecular Weight

316.482

Monoisotopic Molecular Weight

316.261359639

IUPAC Name

9,10-dihydroxyoctadecanoic acid

Traditional Name

9,10-dihydroxystearic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC(O)C(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)

InChI Key

VACHUYIREGFMSP-UHFFFAOYSA-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
Secondary alcohol
1,2-diol
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

dihydroxy monocarboxylic acid (CHEBI:28724 )
hydroxy fatty acid (CHEBI:28724 )
Other Octadecanoids (LMFA02000142 )

Ontology

Not Available

Peanut (FooDB: FOOD00016)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.27	ALOGPS
logP	4.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	89.32 m³·mol⁻¹	ChemAxon
Polarizability	39.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	189.38	32859911
AllCCS	[M+H-H2O]+	186.626	32859911
AllCCS	[M+Na]+	192.657	32859911
AllCCS	[M+NH4]+	191.927	32859911
AllCCS	[M-H]-	183.105	32859911
AllCCS	[M+Na-2H]-	184.282	32859911
AllCCS	[M+HCOO]-	185.733	32859911
DeepCCS	[M+H]+	186.073	30932474
DeepCCS	[M-H]-	182.092	30932474
DeepCCS	[M-2H]-	218.598	30932474
DeepCCS	[M+Na]+	194.888	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 10V, Positive-QTOF	splash10-014j-0294000000-26c1e265f6d9802075ad	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 20V, Positive-QTOF	splash10-01pk-5950000000-85cad97ee7fa4f9b63e1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 40V, Positive-QTOF	splash10-052f-9310000000-ce262a6e28b5c429f9e1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 10V, Negative-QTOF	splash10-014i-0239000000-87e07a26994d4daae6dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 20V, Negative-QTOF	splash10-01bc-1943000000-6f1287dec7d477262886	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 40V, Negative-QTOF	splash10-0a4i-7900000000-487470bee2d85d42bdba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 10V, Positive-QTOF	splash10-000t-0192000000-9efe77ce4b3f4e323d55	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 20V, Positive-QTOF	splash10-060s-9650000000-7fa0d4e22e21686678f7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 40V, Positive-QTOF	splash10-0a4i-9100000000-09d9259c39c1f417c132	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 10V, Negative-QTOF	splash10-014i-0019000000-77bbbd3729d858745b14	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 20V, Negative-QTOF	splash10-014i-0879000000-fbae1d1c8ddc2770b75a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Dihydroxystearic acid 40V, Negative-QTOF	splash10-004m-7940000000-22be68f05b187392b7bb	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28724

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1480411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 9,10-Dihydroxystearic acid (HMDB0302281)

MOL for HMDB0302281 (9,10-Dihydroxystearic acid)

3D MOL for HMDB0302281 (9,10-Dihydroxystearic acid)

3D SDF for HMDB0302281 (9,10-Dihydroxystearic acid)

3D-SDF for HMDB0302281 (9,10-Dihydroxystearic acid)

PDB for HMDB0302281 (9,10-Dihydroxystearic acid)

3D PDB for HMDB0302281 (9,10-Dihydroxystearic acid)

SMILES for HMDB0302281 (9,10-Dihydroxystearic acid)

INCHI for HMDB0302281 (9,10-Dihydroxystearic acid)

Structure for HMDB0302281 (9,10-Dihydroxystearic acid)

3D Structure for HMDB0302281 (9,10-Dihydroxystearic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra