NP-MRD: Showing NP-Card for 13-Hydroxy-9Z,11E-octadecadienoic acid (NP0050315)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:32 UTC

Updated at

2022-04-27 20:52:32 UTC

NP-MRD ID

NP0050315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-Hydroxy-9Z,11E-octadecadienoic acid

Description

13-HODE, also known as 13(S) hode or (S)-coriolic acid, 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, 13-HODE is considered to be an octadecanoid lipid molecule. 13-HODE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13-HODE exists in all living organisms, ranging from bacteria to humans. 13-Hydroxy-9Z,11E-octadecadienoic acid is found in Chlorella pyrenoidosa, Deprea subtriflora, Hernandia ovigera, Lithothamnion corallioides, Mus musculus, Pleurotus pulmonarius and Semibalanus balanoides. 13-Hydroxy-9Z,11E-octadecadienoic acid was first documented in 1997 (PMID: 9561154). An HODE (hydroxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroxy group is at position 13 (with S-configuration) (PMID: 9367845).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304202019522D          

 21 20  0  0  0  0            999 V2000
10009.876910007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.161410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.445910007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.621510007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.906810007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.192010007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.477310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.762610007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.047910007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.333110007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.618310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.186910007.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710008.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410007.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.305810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.021410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.734810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.450310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.165810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410006.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  6  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
M  END
> <DATABASE_ID>
NP0050315

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

> <INCHI_KEY>
HNICUWMFWZBIFP-IRQZEAMPSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.261982452500305

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.191065727333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677909269454

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9881674023842

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706009659333

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.0343

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxyoctadecadienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8685.1048681.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.7688680.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.4328681.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.8938681.409   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8679.5598680.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.2258681.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8676.8918680.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.5578681.409   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8674.2238680.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.8888681.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.5548680.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.2208681.409   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8668.8828680.640   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.2208682.948   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8686.4358680.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8687.7718681.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8689.1078680.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8690.4388681.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8691.7748680.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8693.1098681.409   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8686.4358679.099   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
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                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(13S)-Hydroxyoctadecadienoic acid	ChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(13S)-Hydroxyoctadecadienoate	Generator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
13S-Hydroxyoctadecadienoate	HMDB
13-Hydroxy-9,11-octadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer	HMDB
13-Hydroxyoctadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer	HMDB
13(S) HODE	HMDB
13-Hydroxyoctadecadienoate	HMDB
(+)-Coriolic acid	HMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acid	HMDB
(S)-Coriolic acid	HMDB
(±)-coriolic acid	HMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acid	HMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acid	HMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acid	HMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acid	HMDB
13-Hydroxylinoleic acid	HMDB
13-Hydroxyoctadeca-9,11-dienoic acid	HMDB
13S-HODE	HMDB
13S-Hydroxy-9Z,11E-octadecadienoic acid	HMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid	HMDB
alpha-Artemisolic acid	HMDB
Α-artemisolic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate	HMDB
(9Z,11E)-13-HODE	HMDB
(9Z,11E)-13-Hydroxyoctadecadienoic acid	HMDB
FA(18:2(9Z,11E,13-OH))	HMDB
FA(18:2(9Z,11E,13S-OH))	HMDB
13-HODE	HMDB, MeSH

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

Traditional Name

13-hydroxyoctadecadienoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

InChI Key

HNICUWMFWZBIFP-IRQZEAMPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chlorella pyrenoidosa	Plant	KNApSAcK
Deprea subtriflora	LOTUS Database	35616633
Hernandia ovigera	LOTUS Database	35616633
Lithothamnion corallioides	--	KNApSAcK
Mus musculus	LOTUS Database	35616633
Pleurotus pulmonarius	Fungi	KNApSAcK
Semibalanus balanoides	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:34154 )
Other Octadecanoids (C14762 )
Other Octadecanoids (LMFA02000228 )

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)	4.99	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	37.26 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

HMDB0004667

DrugBank ID

DB06926

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

13-Hydroxyoctadecadienoic acid

METLIN ID

Not Available

PubChem Compound

6443013

PDB ID

Not Available

ChEBI ID

34154

Good Scents ID

Not Available

References

General References

Horrobin DF, Ziboh VA: The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE. Adv Exp Med Biol. 1997;433:291-4. doi: 10.1007/978-1-4899-1810-9_61. [PubMed:9561154 ]
Spindler SA, Sarkar FH, Sakr WA, Blackburn ML, Bull AW, LaGattuta M, Reddy RG: Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biochem Biophys Res Commun. 1997 Oct 29;239(3):775-81. doi: 10.1006/bbrc.1997.7471. [PubMed:9367845 ]

Showing NP-Card for 13-Hydroxy-9Z,11E-octadecadienoic acid (NP0050315)

MOL for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

3D MOL for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

3D SDF for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

3D-SDF for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

PDB for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

3D PDB for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

SMILES for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

INCHI for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

Structure for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)

3D Structure for NP0050315 (13-Hydroxy-9Z,11E-octadecadienoic acid)