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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:20:37 UTC

Update Date

2022-03-07 02:56:01 UTC

HMDB ID

HMDB0038995

Secondary Accession Numbers

HMDB38995

Metabolite Identification

Common Name

(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid

Description

(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 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 small amount of articles have been published on (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid.

Structure

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

HMDB0038995
     RDKit          3D
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
    8.3909    3.0070    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5608    3.0318   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325    2.6577   -1.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3848    2.1717   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.4540   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    0.6024    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -0.1348    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144   -1.0142    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -1.7716    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -2.6540    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856   -3.4097    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -4.3343    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -3.7305   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.4002    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081   -1.7097   -0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8594   -0.4204    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6616    0.4895    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    1.8215    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    2.6496    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742    2.2728    0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    3.9459    1.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7676    2.5479    1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3155    2.4236    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311    4.0477    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2371    4.0891   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0977    2.0904   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -4.4456    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561   -5.3314   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -4.4010   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265   -3.5754   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -1.8146    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7207   -2.6040    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -1.4675   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3864   -2.3694   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -0.6264    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7499    0.0718   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8618    0.0029    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    0.6080   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    1.5917    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222    2.2606    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    4.3767    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  3  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
  3 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
M  END


  Mrv0541 05061310462D          

 21 20  0  0  0  0            999 V2000
   -4.1467   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -1.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  3  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  3  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  3  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  3  0  0  0  0
 16 14  1  0  0  0  0
 17  1  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>
HMDB0038995

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)C#CC#CC#CC#CCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)

> <INCHI_KEY>
MTWGWIOCIREVRF-UHFFFAOYSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.3496

> <EXACT_MASS>
284.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.75158234193983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.1757819693333325

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.251490994381232

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.525879787407715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5635978394149648

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.32369999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038995
     RDKit          3D
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
    8.3909    3.0070    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5608    3.0318   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325    2.6577   -1.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3848    2.1717   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.4540   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    0.6024    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -0.1348    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144   -1.0142    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -1.7716    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -2.6540    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856   -3.4097    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -4.3343    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -3.7305   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.4002    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081   -1.7097   -0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8594   -0.4204    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6616    0.4895    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    1.8215    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    2.6496    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742    2.2728    0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    3.9459    1.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7676    2.5479    1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3155    2.4236    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311    4.0477    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2371    4.0891   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0977    2.0904   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -4.4456    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561   -5.3314   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -4.4010   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265   -3.5754   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -1.8146    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7207   -2.6040    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -1.4675   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3864   -2.3694   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -0.6264    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7499    0.0718   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8618    0.0029    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    0.6080   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    1.5917    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222    2.2606    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    4.3767    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  3  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
  3 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  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      -7.741  -1.389   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.929   3.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   1.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.072   0.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.406   0.151   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.739  -0.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.073  -1.389   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.407  -2.159   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.407  -3.699   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17    1   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    HMDB0038995
HETATM    1  C1  UNL     1       8.391   3.007   0.933  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.561   3.032  -0.333  1.00  0.00           C  
HETATM    3  O1  UNL     1       8.333   2.658  -1.439  1.00  0.00           O  
HETATM    4  C3  UNL     1       6.385   2.172  -0.192  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.416   1.454  -0.079  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.292   0.602   0.035  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.334  -0.135   0.114  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.214  -1.014   0.194  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.272  -1.772   0.249  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.162  -2.654   0.291  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.786  -3.410   0.311  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.920  -4.334   0.328  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.040  -3.730  -0.498  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.405  -2.400   0.147  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.508  -1.710  -0.589  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.859  -0.420   0.083  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.662   0.490   0.106  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.996   1.822   0.764  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.772   2.650   0.744  1.00  0.00           C  
HETATM   20  O2  UNL     1      -1.674   2.273   0.258  1.00  0.00           O  
HETATM   21  O3  UNL     1      -2.788   3.946   1.292  1.00  0.00           O  
HETATM   22  H1  UNL     1       7.768   2.548   1.728  1.00  0.00           H  
HETATM   23  H2  UNL     1       9.316   2.424   0.807  1.00  0.00           H  
HETATM   24  H3  UNL     1       8.631   4.048   1.282  1.00  0.00           H  
HETATM   25  H4  UNL     1       7.237   4.089  -0.546  1.00  0.00           H  
HETATM   26  H5  UNL     1       9.098   2.090  -1.119  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.297  -4.446   1.363  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.656  -5.331  -0.090  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.923  -4.401  -0.516  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.626  -3.575  -1.522  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.443  -1.815   0.108  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.721  -2.604   1.182  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.096  -1.467  -1.614  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.386  -2.369  -0.751  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.165  -0.626   1.153  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.750   0.072  -0.364  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.862   0.003   0.717  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.283   0.608  -0.921  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.340   1.592   1.794  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.822   2.261   0.171  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.629   4.377   1.621  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   25
CONECT    3   26
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7    7
CONECT    7    8
CONECT    8    9    9    9
CONECT    9   10
CONECT   10   11   11   11
CONECT   11   12
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   18   37   38
CONECT   18   19   39   40
CONECT   19   20   20   21
CONECT   21   41
END

HMDB0038995
     RDKit          3D
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
    8.3909    3.0070    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5608    3.0318   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325    2.6577   -1.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3848    2.1717   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.4540   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    0.6024    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -0.1348    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144   -1.0142    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -1.7716    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -2.6540    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856   -3.4097    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -4.3343    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -3.7305   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.4002    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081   -1.7097   -0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8594   -0.4204    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6616    0.4895    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    1.8215    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    2.6496    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742    2.2728    0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    3.9459    1.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7676    2.5479    1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3155    2.4236    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311    4.0477    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2371    4.0891   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0977    2.0904   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -4.4456    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561   -5.3314   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -4.4010   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265   -3.5754   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -1.8146    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7207   -2.6040    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -1.4675   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3864   -2.3694   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -0.6264    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7499    0.0718   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8618    0.0029    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    0.6080   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    1.5917    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222    2.2606    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    4.3767    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  3  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
  3 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoate	Generator
Minquartynoic acid	HMDB
17-Hydroxyoctadeca-9,11,13,15-tetraynoate	Generator

Chemical Formula

C₁₈H₂₀O₃

Average Molecular Weight

284.3496

Monoisotopic Molecular Weight

284.141244506

IUPAC Name

17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

Traditional Name

17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

CAS Registry Number

123154-43-8

SMILES

CC(O)C#CC#CC#CC#CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)

InChI Key

MTWGWIOCIREVRF-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
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0038995)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038995)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038995)

Source

Endogenous

Endogenous (HMDB: HMDB0038995)

Plant

Plant (HMDB: HMDB0038995)

Animal

Animal (HMDB: HMDB0038995)

Exogenous

Food

Food (HMDB: HMDB0038995)

Nut

Nuts (FooDB: FOOD00869)

Exogenous (HMDB: HMDB0038995)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038995)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038995)

Lipid metabolism pathway (HMDB: HMDB0038995)

Cellular process

Cell signaling (HMDB: HMDB0038995)

Biochemical process

Lipid transport (HMDB: HMDB0038995)

Role

Biological role

Energy source (HMDB: HMDB0038995)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038995)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	97 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.92 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0094 g/L	ALOGPS
logP	4.2	ALOGPS
logP	4.18	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-3.6	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	12	ChemAxon
Refractivity	85.32 m³·mol⁻¹	ChemAxon
Polarizability	34.75 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
DarkChem	[M+H]+	177.672	31661259
DarkChem	[M-H]-	174.016	31661259
DeepCCS	[M+H]+	158.401	30932474
DeepCCS	[M-H]-	156.043	30932474
DeepCCS	[M-2H]-	190.707	30932474
DeepCCS	[M+Na]+	165.546	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	172.8	32859911
AllCCS	[M+Na-2H]-	173.8	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid	CC(O)C#CC#CC#CC#CCCCCCCCC(O)=O	4153.0	Standard polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid	CC(O)C#CC#CC#CC#CCCCCCCCC(O)=O	2509.8	Standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid	CC(O)C#CC#CC#CC#CCCCCCCCC(O)=O	2719.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,1TMS,isomer #1	CC(C#CC#CC#CC#CCCCCCCCC(=O)O)O[Si](C)(C)C	2791.9	Semi standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,1TMS,isomer #2	CC(O)C#CC#CC#CC#CCCCCCCCC(=O)O[Si](C)(C)C	2649.5	Semi standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,2TMS,isomer #1	CC(C#CC#CC#CC#CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2797.5	Semi standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,1TBDMS,isomer #1	CC(C#CC#CC#CC#CCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3041.1	Semi standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,1TBDMS,isomer #2	CC(O)C#CC#CC#CC#CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2903.0	Semi standard non polar	33892256
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid,2TBDMS,isomer #1	CC(C#CC#CC#CC#CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3275.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-5590000000-5dbc39d0725272c501e2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-01y9-9453300000-ca2f7ecfa61f4000e85b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 10V, Positive-QTOF	splash10-014r-0090000000-f6c881bfad835b084113	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 20V, Positive-QTOF	splash10-014s-1390000000-87a3685337c0f94e6f7d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 40V, Positive-QTOF	splash10-053u-4920000000-0f6ae8ebaaa92cbac961	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 10V, Negative-QTOF	splash10-001i-0090000000-b5860f044100d26ea57b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 20V, Negative-QTOF	splash10-001r-1190000000-d495a082374849ee3ce8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 40V, Negative-QTOF	splash10-0a4l-9240000000-ca4c473b057a24a41cac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 10V, Negative-QTOF	splash10-001i-0090000000-62479bdb89d4a10b8a95	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 20V, Negative-QTOF	splash10-05o0-4090000000-fe2723ee782d43b9a394	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 40V, Negative-QTOF	splash10-0903-2910000000-aeeda1530ba5756a8f9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 10V, Positive-QTOF	splash10-00kr-0190000000-b68db724379439b790b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 20V, Positive-QTOF	splash10-05tb-0690000000-32fb095544dd95f717c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid 40V, Positive-QTOF	splash10-00g0-1900000000-884e385d19cad37b5ac2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB018483

KNApSAcK ID

C00046157

Chemspider ID

4059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4204

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1873311

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. Epub 2007 Mar 20. [PubMed:17374880 ]
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Showing metabocard for (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid (HMDB0038995)

MOL for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

3D MOL for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

3D SDF for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

3D-SDF for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

PDB for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

3D PDB for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

SMILES for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

INCHI for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

Structure for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

3D Structure for HMDB0038995 ((S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra