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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:58:07 UTC

Update Date

2021-09-23 20:58:07 UTC

HMDB ID

HMDB0302825

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid

Description

(11s,12s,13s)-epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 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 (11s,12s,13s)-epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (11s,12s,13s)-epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid can be found in rice, which makes (11s,12s,13s)-epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302825
     RDKit          3D
(11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid
 52 52  0  0  0  0  0  0  0  0999 V2000
    8.9027   -0.7243   -2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223    0.0595   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356    0.2809   -2.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4390   -0.1660   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310   -0.9385   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.2204    0.2696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7338   -0.8111    1.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930   -0.8973    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5436   -0.0568    0.5524 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7700   -0.2996   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -0.4203    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3084    0.1092    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200    1.0831    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    0.5282    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.2325    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570   -0.3225    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902    0.6094    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7019   -0.0720    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6119    0.7622   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0627    1.0539   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9712    0.6479   -2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8188    1.8677   -2.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7565   -1.7984   -1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9240   -0.4538   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8447   -0.6109   -3.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6524   -0.2841   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2914    1.0888   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7384    0.8452   -3.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.0676   -2.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143   -1.8784   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959   -1.3041   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.8939    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.9488    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848    1.0090    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956   -1.2321   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.1249    2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -0.1879    3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955    1.9889    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177    1.4528    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -0.4344    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    1.2078    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    1.1643    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -0.5136    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -0.4300    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.3310    1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568    0.8574   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.5304    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2229   -0.2447    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5093   -1.0546    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7266    1.7505    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    0.2731   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8372    1.6949   -3.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  1  0
 20 21  2  0
 20 22  1  0
  8  6  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END


  Mrv0541 02241212512D          

 22 22  0  0  0  0            999 V2000
   -2.4971    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0682    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3607    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3221    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114   -0.1841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6904    0.0875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7572   -0.9946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5154    0.0875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1029    0.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2299   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0268   -0.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7412   -0.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7412   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4557   -1.7614    0.0000 C   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  2  0  0  0  0
  1 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 14 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302825

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C[C@@H]1O[C@H]1[C@@H](O)\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O4/c1-2-3-9-13-16-18(22-16)15(19)12-10-7-5-4-6-8-11-14-17(20)21/h3,9-10,12,15-16,18-19H,2,4-8,11,13-14H2,1H3,(H,20,21)/b9-3-,12-10-/t15-,16-,18-/m0/s1

> <INCHI_KEY>
XHMGEKKHSKIGMI-AUBGSNCASA-N

> <FORMULA>
C18H30O4

> <MOLECULAR_WEIGHT>
310.4284

> <EXACT_MASS>
310.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.79500273310661

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11S)-11-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-9-enoic acid

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.202962085666666

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.749672551619966

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283416805

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3456932262504004

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
89.24719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,11S)-11-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302825
     RDKit          3D
(11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid
 52 52  0  0  0  0  0  0  0  0999 V2000
    8.9027   -0.7243   -2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223    0.0595   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356    0.2809   -2.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4390   -0.1660   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310   -0.9385   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.2204    0.2696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7338   -0.8111    1.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930   -0.8973    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5436   -0.0568    0.5524 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7700   -0.2996   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -0.4203    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3084    0.1092    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200    1.0831    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    0.5282    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.2325    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570   -0.3225    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902    0.6094    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7019   -0.0720    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6119    0.7622   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0627    1.0539   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9712    0.6479   -2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8188    1.8677   -2.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7565   -1.7984   -1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9240   -0.4538   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6524   -0.2841   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2914    1.0888   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6143   -1.8784   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959   -1.3041   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.8939    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.9488    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848    1.0090    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956   -1.2321   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.1249    2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -0.1879    3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1322   -0.4300    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.3310    1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568    0.8574   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.5304    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2229   -0.2447    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5093   -1.0546    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7266    1.7505    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    0.2731   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8372    1.6949   -3.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  1  0
 20 21  2  0
 20 22  1  0
  8  6  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.661   0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.328  -0.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.994   0.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.660  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.673   0.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.007  -0.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.341   0.605   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.675  -0.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.008   0.605   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.342  -0.165   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.008   2.145   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.201   0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.301  -0.344   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.755   0.163   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.013  -1.857   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -10.295   0.163   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.525   1.497   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -11.629  -0.607   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.117  -0.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.450  -0.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.450  -2.518   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -15.784  -3.288   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
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                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   14                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0302825
HETATM    1  C1  UNL     1       8.903  -0.724  -2.068  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.822   0.059  -1.343  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.636   0.281  -2.170  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.439  -0.166  -1.834  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.131  -0.938  -0.602  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.127  -0.220   0.270  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.734  -0.811   1.457  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.793  -0.897   0.400  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.544  -0.057   0.552  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.770  -0.300  -0.596  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.857  -0.420   1.793  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.308   0.109   2.086  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.020   1.083   1.234  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.345   0.528   0.828  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.217   0.233   2.015  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.557  -0.323   1.658  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.390   0.609   0.786  1.00  0.00           C  
HETATM   18  C16 UNL     1      -6.702  -0.072   0.511  1.00  0.00           C  
HETATM   19  C17 UNL     1      -7.612   0.762  -0.344  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.063   1.054  -1.658  1.00  0.00           C  
HETATM   21  O3  UNL     1      -5.971   0.648  -2.108  1.00  0.00           O  
HETATM   22  O4  UNL     1      -7.819   1.868  -2.514  1.00  0.00           O  
HETATM   23  H1  UNL     1       8.757  -1.798  -1.756  1.00  0.00           H  
HETATM   24  H2  UNL     1       9.924  -0.454  -1.731  1.00  0.00           H  
HETATM   25  H3  UNL     1       8.845  -0.611  -3.153  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.652  -0.284  -0.317  1.00  0.00           H  
HETATM   27  H5  UNL     1       8.291   1.089  -1.205  1.00  0.00           H  
HETATM   28  H6  UNL     1       6.738   0.845  -3.115  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.622   0.068  -2.544  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.614  -1.878  -0.973  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.996  -1.304  -0.053  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.096   0.894   0.185  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.687  -1.949   0.052  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.885   1.009   0.569  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.496  -1.232  -0.613  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.299  -1.125   2.481  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.774  -0.188   3.016  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.196   1.989   1.888  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.418   1.453   0.394  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.237  -0.434   0.269  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.879   1.208   0.128  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.377   1.164   2.599  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.731  -0.514   2.679  1.00  0.00           H  
HETATM   44  H22 UNL     1      -5.132  -0.430   2.609  1.00  0.00           H  
HETATM   45  H23 UNL     1      -4.513  -1.331   1.214  1.00  0.00           H  
HETATM   46  H24 UNL     1      -4.857   0.857  -0.132  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.631   1.530   1.394  1.00  0.00           H  
HETATM   48  H26 UNL     1      -7.223  -0.245   1.484  1.00  0.00           H  
HETATM   49  H27 UNL     1      -6.509  -1.055   0.010  1.00  0.00           H  
HETATM   50  H28 UNL     1      -7.727   1.750   0.193  1.00  0.00           H  
HETATM   51  H29 UNL     1      -8.612   0.273  -0.405  1.00  0.00           H  
HETATM   52  H30 UNL     1      -7.837   1.695  -3.522  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    4   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7    8   32
CONECT    7    8
CONECT    8    9   33
CONECT    9   10   11   34
CONECT   10   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   21   22
CONECT   22   52
END

HMDB0302825
     RDKit          3D
(11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid
 52 52  0  0  0  0  0  0  0  0999 V2000
    8.9027   -0.7243   -2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223    0.0595   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356    0.2809   -2.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4390   -0.1660   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310   -0.9385   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.2204    0.2696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7338   -0.8111    1.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930   -0.8973    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5436   -0.0568    0.5524 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7700   -0.2996   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -0.4203    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3084    0.1092    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200    1.0831    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    0.5282    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.2325    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570   -0.3225    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902    0.6094    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7019   -0.0720    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6119    0.7622   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0627    1.0539   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9712    0.6479   -2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8188    1.8677   -2.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7565   -1.7984   -1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9240   -0.4538   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8447   -0.6109   -3.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6524   -0.2841   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2914    1.0888   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7384    0.8452   -3.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.0676   -2.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143   -1.8784   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959   -1.3041   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.8939    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.9488    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848    1.0090    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956   -1.2321   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.1249    2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -0.1879    3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955    1.9889    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177    1.4528    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -0.4344    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    1.2078    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    1.1643    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -0.5136    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -0.4300    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.3310    1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568    0.8574   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.5304    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2229   -0.2447    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5093   -1.0546    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7266    1.7505    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    0.2731   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8372    1.6949   -3.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  1  0
 20 21  2  0
 20 22  1  0
  8  6  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,11S)-11-Hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-9-enoate	Generator
(11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-Oate	Generator

Chemical Formula

C₁₈H₃₀O₄

Average Molecular Weight

310.4284

Monoisotopic Molecular Weight

310.214409448

IUPAC Name

(9Z,11S)-11-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-9-enoic acid

Traditional Name

(9Z,11S)-11-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-9-enoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/C[C@@H]1O[C@H]1[C@@H](O)\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O4/c1-2-3-9-13-16-18(22-16)15(19)12-10-7-5-4-6-8-11-14-17(20)21/h3,9-10,12,15-16,18-19H,2,4-8,11,13-14H2,1H3,(H,20,21)/b9-3-,12-10-/t15-,16-,18-/m0/s1

InChI Key

XHMGEKKHSKIGMI-AUBGSNCASA-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
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

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	4.51	ALOGPS
logP	4.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.25 m³·mol⁻¹	ChemAxon
Polarizability	36.8 Å³	ChemAxon
Number of Rings	1	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]+	184.094	32859911
AllCCS	[M+H-H2O]+	181.154	32859911
AllCCS	[M+Na]+	187.597	32859911
AllCCS	[M+NH4]+	186.816	32859911
AllCCS	[M-H]-	183.098	32859911
AllCCS	[M+Na-2H]-	184.399	32859911
AllCCS	[M+HCOO]-	185.981	32859911
DeepCCS	[M+H]+	180.409	30932474
DeepCCS	[M-H]-	178.013	30932474
DeepCCS	[M-2H]-	211.288	30932474
DeepCCS	[M+Na]+	186.374	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 - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 10V, Positive-QTOF	splash10-03dl-5397000000-af7c490b2ea5ad9b4ffd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 20V, Positive-QTOF	splash10-001i-9610000000-230bb2911295e417fac6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 40V, Positive-QTOF	splash10-100u-9200000000-7a54a6d9d362dac77a99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 10V, Negative-QTOF	splash10-0a4i-0529000000-e0a11e6dc2fc8f87522c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 20V, Negative-QTOF	splash10-0cdi-1932000000-edf278cc291da170a466	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 40V, Negative-QTOF	splash10-0006-9200000000-90a46a1a875e4be2fad6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 10V, Positive-QTOF	splash10-03fu-2693000000-e2e1b03e12a16f4f639f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 20V, Positive-QTOF	splash10-06ur-9871000000-2c9564957510cd87ced7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 40V, Positive-QTOF	splash10-05mo-9200000000-9c522ace71775345c5ad	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 10V, Negative-QTOF	splash10-0a4i-0029000000-76036cb86db5f0c5083c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 20V, Negative-QTOF	splash10-0a4l-2595000000-44b4f3d7acdcb536ef4e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid 40V, Negative-QTOF	splash10-0006-9430000000-f5c404823c63d99c8d49	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

FDB006382

KNApSAcK ID

Not Available

Chemspider ID

10335849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10957878

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid (HMDB0302825)

MOL for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

3D MOL for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

3D SDF for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

3D-SDF for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

PDB for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

3D PDB for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

SMILES for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

INCHI for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

Structure for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

3D Structure for HMDB0302825 ((11S,12S,13S)-Epoxy-hydroxyoctadeca-cis-9-cis-15-dien-1-oic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra