NP-MRD: Showing NP-Card for dimorphecolic acid (NP0192356)

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Record Information

Version

2.0

Created at

2022-09-04 09:32:49 UTC

Updated at

2022-09-04 09:32:49 UTC

NP-MRD ID

NP0192356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dimorphecolic acid

Description

9-HODE belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 9-HODE is considered to be an octadecanoid lipid molecule. Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma is a ligand-activated transcription factor that regulates gene expression in response to various mediators such as 15-deoxy-Delta12, 14-prostaglandin J2 (15d-PGJ2) and oxidized linoleic acid (9- and 13-HODE). Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. 9-HODE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 9(S)-HODE inhibits proliferation of NHEK cells by suppressing DNA synthesis and arresting the cell cycle in the G0/1-phase. 9-HODE, which is a trans isomer of 9(S)-HODE, is an endogenous fatty acid PPARgamma agonist synthesized in the body from linoleic acid. 9-HODE-G2A signaling plays proinflammatory roles in skin under oxidative conditions. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1, remains incompletely understood. Alpha-dimorphecolic activates Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma in human endothelial cells increasing plasminogen activator inhibitor type-1 expression. dimorphecolic acid was first documented in 2005 (PMID: 16236715). Adipocytes also produce PAI-1, suggesting possible common regulatory pathways between adipocytes and ECs (PMID: 16647253).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
    6.0489    2.3580    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469    1.0827    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.1275   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9847   -1.4179    0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6812   -1.6238    1.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -1.6007    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5183   -0.7688    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3995   -0.8260   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925   -0.0105   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631   -0.0107   -1.3463 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3844    0.4763   -2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -1.3992   -1.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -1.9319   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -1.0365    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0352   -0.9753   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1213   -0.0953    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6890    1.3012    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7904    2.1359    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9094    2.2418   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0355    2.7211    0.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7869    1.8214   -1.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1439    2.5066   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4555    2.2991   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6720    3.1970    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    1.1333    1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    1.0292    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3556   -0.0884   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0883   -0.0714   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -2.2362   -0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7925   -1.5306    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248   -2.6600    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5522   -0.9519    2.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -2.3492   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5229   -0.0208    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -1.5833   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    0.7506    0.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698    0.6681   -1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746    1.4642   -2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4653   -2.0707   -1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -1.4881   -2.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327   -2.0106    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1940   -2.9846   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -0.0175    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2229   -1.4016    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7100   -0.6279   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730   -1.9971   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0258   -0.1466   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4442   -0.5142    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    1.7659   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453    1.3678    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    3.1677    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1730    1.7607    1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4941    1.3261   -1.8943 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 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 21  1  0
 19 20  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END


  Mrv1652308071918032D          

 21 20  0  0  0  0            999 V2000
   18.4275  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7124  -19.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9978  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2831  -19.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5680  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8534  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1466  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1387  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8612  -20.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4319  -20.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4236  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5763  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7169  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7090  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2909  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022  -20.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0000  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2876  -19.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0000  -19.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875  -19.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725  -20.3913    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  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0192356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C\C=C\C(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+

> <INCHI_KEY>
NPDSHTNEKLQQIJ-SIGMCMEVSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.97573719314828

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10E,12E)-9-hydroxyoctadeca-10,12-dienoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.191065727333333

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677864657474

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745528848431

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759708475080179

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.03429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimorphecolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-AUG-19         0                                  
HETATM    1  C   UNK     0      34.398 -38.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.063 -37.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.729 -38.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.395 -37.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.060 -38.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.726 -37.294   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.074 -37.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.392 -38.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.408 -38.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.740 -38.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.057 -37.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.742 -37.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.405 -37.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.723 -38.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.076 -38.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.071 -38.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.400 -37.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.737 -37.294   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      22.400 -35.766   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.737 -35.766   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.402 -38.064   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    8                                                       
CONECT    7    9   10                                                       
CONECT    8    6   11                                                       
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   19                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxy-10,12-octadecadienoate	HMDB
9-Hydroxy-10,12-octadecadienoic acid	HMDB
9-Hydroxy-10E,12E-octadecadienoate	HMDB
9-Hydroxy-10E,12E-octadecadienoic acid	HMDB
9-Hydroxy-trans-10,trans-12-octadecadienoate	HMDB
9-Hydroxy-trans-10,trans-12-octadecadienoic acid	HMDB
9-Hydroxylinoleic acid	HMDB
alpha-Dimorphecolic acid	HMDB
Dimorphecolic acid	HMDB
9-OH-18:2DElta(10t,12t)	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomer	HMDB
Dimorphecolate	Generator
9-HODE	MeSH

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

(10E,12E)-9-hydroxyoctadeca-10,12-dienoic acid

Traditional Name

dimorphecolic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C=C\C(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+

InChI Key

NPDSHTNEKLQQIJ-SIGMCMEVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000152 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.88	ALOGPS
logP	5.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.6	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	14	ChemAxon
Refractivity	90.03 m³·mol⁻¹	ChemAxon
Polarizability	37.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010223

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031387

KNApSAcK ID

Not Available

Chemspider ID

4446072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

9-Hydroxyoctadecadienoic acid

METLIN ID

Not Available

PubChem Compound

5282945

PDB ID

Not Available

ChEBI ID

595882

Good Scents ID

Not Available

References

General References

Hampel JK, Brownrigg LM, Vignarajah D, Croft KD, Dharmarajan AM, Bentel JM, Puddey IB, Yeap BB: Differential modulation of cell cycle, apoptosis and PPARgamma2 gene expression by PPARgamma agonists ciglitazone and 9-hydroxyoctadecadienoic acid in monocytic cells. Prostaglandins Leukot Essent Fatty Acids. 2006 May;74(5):283-93. doi: 10.1016/j.plefa.2006.03.002. Epub 2006 May 2. [PubMed:16647253 ]
Obinata H, Hattori T, Nakane S, Tatei K, Izumi T: Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A. J Biol Chem. 2005 Dec 9;280(49):40676-83. doi: 10.1074/jbc.M507787200. Epub 2005 Oct 19. [PubMed:16236715 ]
LOTUS database [Link]

Showing NP-Card for dimorphecolic acid (NP0192356)

MOL for NP0192356 (dimorphecolic acid)

3D MOL for NP0192356 (dimorphecolic acid)

3D SDF for NP0192356 (dimorphecolic acid)

3D-SDF for NP0192356 (dimorphecolic acid)

PDB for NP0192356 (dimorphecolic acid)

3D PDB for NP0192356 (dimorphecolic acid)

SMILES for NP0192356 (dimorphecolic acid)

INCHI for NP0192356 (dimorphecolic acid)

Structure for NP0192356 (dimorphecolic acid)

3D Structure for NP0192356 (dimorphecolic acid)