NP-MRD: Showing NP-Card for (10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid (NP0234854)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 17:09:25 UTC

Updated at

2022-09-06 17:09:26 UTC

NP-MRD ID

NP0234854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid

Description

9-HODE, also known as (10E,12Z)-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. A HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9. (10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid is found in Carthamus oxyacanthus and Valeriana fauriei. (10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid was first documented in 2012 (PMID: 22790953). 9-HODE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 24760997).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
   -8.5882    0.8309    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6617    0.5920   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9190   -0.6941   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0541   -0.8173    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9704    0.2301    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.0468    1.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503   -0.3175    1.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -0.3725    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597   -0.6629    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -0.7397   -0.6426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5272   -0.1101   -1.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795   -0.1683   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -0.2169   -1.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437    0.3664   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779   -0.3879    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121    0.1910    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6009    0.1628   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9421    0.7176   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6103   -0.0134    0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1168   -1.0336    1.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8535    0.4143    1.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3618    0.1736    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6556    0.6256   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5751    1.9050    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3154    0.5327   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0252    1.4764   -1.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6767   -1.5136   -0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3397   -0.8846   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5314   -1.8024    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6007   -0.8229    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4175    1.2533    0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979    0.2994   -0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7346   -0.0253    2.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775   -0.5075    2.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171   -0.2091   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615   -0.8385    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499   -1.8099   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    0.7639   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844    0.8667    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738   -0.8411    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241    0.3311   -2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872   -1.2591   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    1.4190   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3071    0.4722   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3732   -1.4758   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353   -0.2862    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9703   -0.2653    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295    1.2726    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7368   -0.8930   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165    0.7685   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863    1.8264   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5836    0.6177   -1.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5201    0.9061    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  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
  6 33  1  0
  5 31  1  0
  5 32  1  0
  4 29  1  0
  4 30  1  0
  3 27  1  0
  3 28  1  0
  2 25  1  0
  2 26  1  0
  1 22  1  0
  1 23  1  0
  1 24  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

      
  Mrv1652311101716532D          

 25 24  0  0  0  0            999 V2000
    2.8065    5.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    4.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    2.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8078    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5223    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0234854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])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-ZJHFMPGASA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.42721081023866

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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>
90.03429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-NOV-17         0                                  
HETATM    1  H   UNK     0       5.239  10.725   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.906  10.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.906  12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.240  13.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.240  14.575   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574  15.345   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       5.239   7.645   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       9.240   8.415   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       6.573   5.335   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
(10E,12Z)-9-HODE	ChEBI
9-Hydroxy-10E,12Z-octadecadienoic acid	ChEBI
9-Hydroxy-trans-10,cis-12-octadecadienoic acid	ChEBI
9-Hydroxy-10E,12Z-octadecadienoate	Generator
9-Hydroxy-trans-10,cis-12-octadecadienoate	Generator
9-Hydroxylinoleic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomer	MeSH
Dimorphecolic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomer	MeSH
9-OH-18:2DElta(10t,12t)	MeSH
9-Hydroxy-10,12-octadecadienoic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomer	MeSH
(10E,12Z)-9-hydroxy-10,12-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-10E,12Z-octadecadienoic acid	SMPDB, HMDB, ChEBI
9-hydroxy-(10E,12Z)-octadeca-10,12-dienoic acid	SMPDB, HMDB
9-hydroxy-10(E),12(Z)-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-10-trans-12-cis-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-trans-10-cis-12-octadecadienoic acid	SMPDB, HMDB
9-hydroxyoctadeca-10,12-dienoic acid	SMPDB, HMDB
9-(E,Z)-HODE	SMPDB, HMDB
9-HODE	SMPDB, HMDB
9-hydroxylinoleic acid	SMPDB, HMDB, MeSH
(10E,12Z)-9-HODE	SMPDB, HMDB, ChEBI

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4510 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])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-ZJHFMPGASA-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
Carthamus oxyacanthus	LOTUS Database	35616633
Valeriana fauriei	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

HODE (CHEBI:72651 )
Other Octadecanoids (LMFA02000151 )

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	37.43 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

HMDB0062652

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

9-Hydroxyoctadecadienoic acid

METLIN ID

Not Available

PubChem Compound

5282944

PDB ID

Not Available

ChEBI ID

72651

Good Scents ID

Not Available

References

General References

Yuki K, Ikeda M, Miyamoto K, Ohno O, Yamada K, Uemura D: Isolation of 9-hydroxy-10E,12Z-octadecadienoic acid, an inhibitor of fat accumulation from Valeriana fauriei. Biosci Biotechnol Biochem. 2012;76(6):1233-5. doi: 10.1271/bbb.110994. Epub 2012 Jun 7. [PubMed:22790953 ]
Nieman DC, Shanely RA, Luo B, Meaney MP, Dew DA, Pappan KL: Metabolomics approach to assessing plasma 13- and 9-hydroxy-octadecadienoic acid and linoleic acid metabolite responses to 75-km cycling. Am J Physiol Regul Integr Comp Physiol. 2014 Jul 1;307(1):R68-74. doi: 10.1152/ajpregu.00092.2014. Epub 2014 Apr 23. [PubMed:24760997 ]
LOTUS database [Link]

Showing NP-Card for (10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid (NP0234854)

MOL for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

3D MOL for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

3D SDF for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

3D-SDF for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

PDB for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

3D PDB for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

SMILES for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

INCHI for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

Structure for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)

3D Structure for NP0234854 ((10e,12z)-9-hydroxyoctadeca-10,12-dienoic acid)