NP-MRD: Showing NP-Card for 9-Hydroxy-10E,12Z-octadecadienoic acid (NP0050336)

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Record Information

Version

2.0

Created at

2022-04-27 20:53:26 UTC

Updated at

2022-04-27 20:53:26 UTC

NP-MRD ID

NP0050336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Hydroxy-10E,12Z-octadecadienoic acid

Description

9(R)-HODE, also known as 9R-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(R)-hode is considered to be an octadecanoid. 9-Hydroxy-10E,12Z-octadecadienoic acid is found in Artemisia armeniaca, Carthamus oxyacanthus, Discopodium penninervium and Lithothamnion corallioides. 9-Hydroxy-10E,12Z-octadecadienoic acid was first documented in 2020 (PMID: 32540064). Based on a literature review very few articles have been published on 9(R)-HODE (PMID: 32248066).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222532D          

 21 20  0  0  1  0            999 V2000
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.0329    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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 11 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050336

> <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-/m0/s1

> <INCHI_KEY>
NPDSHTNEKLQQIJ-WXUVIADPSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.659796903125454

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,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>
9(R)-hode

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.906  -6.105   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.240  -3.795   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      19.909  -5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.910  -6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.244  -5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.244  -3.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.578  -3.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.578  -1.485   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.912  -0.715   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.912   0.825   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      19.909  -3.795   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   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                                                       
CONECT   20   19                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
9R-HODE	ChEBI
9R-Hydroxy-10E,12Z-octadecadienoic acid	ChEBI
9R-Hydroxy-10E,12Z-octadecadienoate	Generator

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4510 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

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

Traditional Name

9(R)-hode

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-/m0/s1

InChI Key

NPDSHTNEKLQQIJ-WXUVIADPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia armeniaca	LOTUS Database	35616633
Carthamus oxyacanthus	LOTUS Database	35616633
Discopodium penninervium	LOTUS Database	35616633
Lithothamnion corallioides	--	KNApSAcK

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:78730 )
Other Octadecanoids (LMFA02000036 )

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	36.66 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17220742

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061059

PDB ID

Not Available

ChEBI ID

78730

Good Scents ID

Not Available

References

General References

Cebo M, Fu X, Gawaz M, Chatterjee M, Lammerhofer M: Enantioselective ultra-high performance liquid chromatography-tandem mass spectrometry method based on sub-2microm particle polysaccharide column for chiral separation of oxylipins and its application for the analysis of autoxidized fatty acids and platelet releasates. J Chromatogr A. 2020 Aug 2;1624:461206. doi: 10.1016/j.chroma.2020.461206. Epub 2020 May 16. [PubMed:32540064 ]
Zheng X, Xie X, Liu Y, Cong J, Fan J, Fang Y, Liu N, He Z, Liu J: Deciphering the mechanism of carbon sources inhibiting recolorization in the removal of refractory dye: Based on an untargeted LC-MS metabolomics approach. Bioresour Technol. 2020 Jul;307:123248. doi: 10.1016/j.biortech.2020.123248. Epub 2020 Mar 24. [PubMed:32248066 ]

Showing NP-Card for 9-Hydroxy-10E,12Z-octadecadienoic acid (NP0050336)

MOL for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

3D MOL for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

3D SDF for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

3D-SDF for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

PDB for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

3D PDB for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

SMILES for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

INCHI for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

Structure for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)

3D Structure for NP0050336 (9-Hydroxy-10E,12Z-octadecadienoic acid)