NP-MRD: Showing NP-Card for 9(s)-hode (NP0162959)

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Record Information

Version

2.0

Created at

2022-09-02 21:28:33 UTC

Updated at

2022-09-02 21:28:33 UTC

NP-MRD ID

NP0162959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9(s)-hode

Description

Alpha-Dimorphecolic acid, also known as a-dimorphecolate or (9S)-hydroxyoctadecadienoate, 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. 9(s)-hode is found in Turbinellus floccosus. 9(s)-hode was first documented in 1999 (PMID: 10073956). Alpha-Dimorphecolic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16647253) (PMID: 16236715) (PMID: 18034171).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
   -6.8941   -0.8519   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7847    0.1613   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5862    1.0619    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2560    0.4200    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -0.3477    1.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838   -1.5032    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9162   -1.7182    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8415   -0.7848   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -1.0370   -0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279   -0.0659   -1.1464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2534    1.1850   -1.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812    0.0929    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201    1.0615    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    0.6165   -0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636   -0.7078   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.7550    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606    0.2199    0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5548   -0.0205   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6139    0.9932    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4579    0.8991    1.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7162    2.1253   -0.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640   -0.3171   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9011   -1.5669   -1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7946   -1.3592    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1734    0.7819   -1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8702   -0.2981   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8178    1.8373    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    1.6887    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719    1.2511    2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -0.2079    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509    0.3746    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -0.6938    2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6444   -2.2961    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -2.6391   -0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7673    0.1139    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8897   -1.9321   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.4655   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143    1.6201   -2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -0.9106    0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789    0.4653    0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357    2.0858   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    1.2076    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294    1.4336   -0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.5624   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.0364   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -1.4699   -0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755   -0.6623    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692   -1.7773    0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824    0.0991    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1478    1.2733    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1599    0.1541   -1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9786   -1.0431    0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8960    2.6819   -0.8390 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  6
 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


  Mrv1652310111919002D          

 21 20  0  0  0  0            999 V2000
 9997.8938 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6086 9998.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3238 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0375 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7532 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5780 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2938 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0094 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7230 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4387 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1543 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6086 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1787 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4639 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7491 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0342 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3192 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6044 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8896 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1727 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8896 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
 10 11  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
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0162959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C=C/[C@@H](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+/t17-/m1/s1

> <INCHI_KEY>
NPDSHTNEKLQQIJ-UINYOVNOSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.228152858699026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E,12Z)-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>
90.0343

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-dimorphecolic

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0    8662.7358663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0698663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.4058663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.7378663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.0738663.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.6128663.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.9488663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.2848663.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.6168663.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.9528663.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8676.2888663.832   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8664.0698665.373   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8661.4008663.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.0668663.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.7328663.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8657.3978663.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8656.0638663.832   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8654.7288663.064   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8653.3948663.832   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8652.0568663.064   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8653.3948665.373   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3   12                                                  
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                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    1   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   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoic acid	ChEBI
(9S)-Hydroxyoctadecadienoic acid	ChEBI
(9S)-Hydroxyoctadecadinoiec acid	ChEBI
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoate	Generator
(9S)-Hydroxyoctadecadienoate	Generator
a-Dimorphecolate	Generator
a-Dimorphecolic acid	Generator
alpha-Dimorphecolate	Generator
Α-dimorphecolate	Generator
Α-dimorphecolic acid	Generator
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoate	HMDB
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid	HMDB
9(S)-HODE	HMDB
9S-Hydroxy-10E,12Z-octadecadienoate	HMDB
9S-Hydroxy-10E,12Z-octadecadienoic acid	HMDB
alpha-Dimorphecolic	HMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoate	HMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoic acid	HMDB
9-Hydroxy-10,12-octadecadienoic acid	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomer	HMDB
9-HODE	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomer	HMDB
9-Hydroxylinoleic acid	HMDB
Dimorphecolic acid	HMDB
9-OH-18:2DElta(10t,12t)	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
9-Hydroxyoctadecadienoic acid	HMDB
9S-HOD acid	HMDB
(+)-alpha-Dimorphecolic acid	HMDB
(+)-Α-dimorphecolic acid	HMDB
(10E,12Z)-9-Hydroxy-10,12-octadecadienoic acid	HMDB
(9S,10E,12Z)-9-Hydroxy-10,12-octadecadienoic acid	HMDB
(±)-alpha-dimorphecolic acid	HMDB
(±)-α-dimorphecolic acid	HMDB
9-(e,Z)-HODE	HMDB
9-Hydroxy-(10E,12Z)-octadeca-10,12-dienoic acid	HMDB
9-Hydroxy-10(e),12(Z)-octadecadienoic acid	HMDB
9-Hydroxy-10-trans,12-cis-octadecadienoic acid	HMDB
9S-HODE	HMDB
alpha-Dimorphecolic acid	HMDB

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

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

Traditional Name

α-dimorphecolic

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C=C/[C@@H](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+/t17-/m1/s1

InChI Key

NPDSHTNEKLQQIJ-UINYOVNOSA-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

Species Name	Source	Reference
Turbinellus floccosus	LOTUS Database	35616633

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

(10E,12Z)-9-HODE (CHEBI:34496 )
Other Octadecanoids (C14767 )
Other Octadecanoids (LMFA02000188 )

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	37.23 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

HMDB0004670

DrugBank ID

DB07302

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003060

KNApSAcK ID

Not Available

Chemspider ID

4472255

KEGG Compound ID

C14767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

9-Hydroxyoctadecadienoic_acid

METLIN ID

Not Available

PubChem Compound

5312830

PDB ID

9HO

ChEBI ID

34496

Good Scents ID

Not Available

References

General References

Marx N, Bourcier T, Sukhova GK, Libby P, Plutzky J: PPARgamma activation in human endothelial cells increases plasminogen activator inhibitor type-1 expression: PPARgamma as a potential mediator in vascular disease. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):546-51. doi: 10.1161/01.atv.19.3.546. [PubMed:10073956 ]
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 ]
Hattori T, Obinata H, Ogawa A, Kishi M, Tatei K, Ishikawa O, Izumi T: G2A plays proinflammatory roles in human keratinocytes under oxidative stress as a receptor for 9-hydroxyoctadecadienoic acid. J Invest Dermatol. 2008 May;128(5):1123-33. doi: 10.1038/sj.jid.5701172. Epub 2007 Nov 22. [PubMed:18034171 ]
LOTUS database [Link]

Showing NP-Card for 9(s)-hode (NP0162959)

MOL for NP0162959 (9(s)-hode)

3D MOL for NP0162959 (9(s)-hode)

3D SDF for NP0162959 (9(s)-hode)

3D-SDF for NP0162959 (9(s)-hode)

PDB for NP0162959 (9(s)-hode)

3D PDB for NP0162959 (9(s)-hode)

SMILES for NP0162959 (9(s)-hode)

INCHI for NP0162959 (9(s)-hode)

Structure for NP0162959 (9(s)-hode)

3D Structure for NP0162959 (9(s)-hode)