MiMeDB: Showing metabocard for (9Z,11E)-13-HODE (MMDBc0000789)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 21:51:50 UTC

Update Date

2024-04-30 19:33:42 UTC

Metabolite ID

MMDBc0000789

Metabolite Identification

Common Name

(9Z,11E)-13-HODE

Description

(9Z,11E)-13-HODE or (9Z,11E)-13-hydroxyoctadecadienoic acid is a hydroxy fatty acid. In humans, fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652309151721502D          

 21 20  0  0  1  0            999 V2000
    5.2477  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9621  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6766  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3910  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8200  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5345  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3595  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7884  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5029  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2174  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9318  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6463  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3608  -11.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0752  -10.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0753  -10.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7897  -11.3530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3909  -12.1779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187  -10.9403    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
  1 13  1  0  0  0  0
 12 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 19  1  0  0  0  0
 17 18  2  0  0  0  0
  4 20  1  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000789

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC(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+

> <INCHI_KEY>
HNICUWMFWZBIFP-BSZOFBHHSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.53117396068553

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E)-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>
90.03429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-17         0                                  
HETATM    1  C   UNK     0       9.796 -20.422   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.129 -21.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.463 -20.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.797 -21.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.130 -20.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.464 -21.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.798 -20.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.338 -20.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.671 -21.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.005 -20.422   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.339 -21.192   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.672 -20.422   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.462 -21.192   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.006 -21.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.340 -20.422   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.673 -21.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.007 -20.422   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      30.007 -18.882   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      31.341 -21.192   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.796 -22.732   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.128 -20.422   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
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   14                                                       
CONECT   13    1   21                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    4                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

Synonyms

Value	Source
13-Hydroxy-9Z,11E-octadecadienoic acid	ChEBI
13-Hydroxy-cis-9,trans-11-octadecadienoic acid	ChEBI
13-Hydroxy-9Z,11E-octadecadienoate	Generator
13-Hydroxy-cis-9,trans-11-octadecadienoate	Generator
Coriolate	Generator
13-HODE	MeSH
13-Hydroxy-9,11-octadecadienoic acid, (e,e)-isomer	MeSH
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer	MeSH
13-HODD	MeSH
13-LOX	MeSH
13-Hydroxy-9,11-octadecadienoic acid	MeSH
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer	MeSH
13-Hydroxyoctadecadienoic acid	MeSH
13-Hydroxy-9,11-octadecadienoic acid, (R)-(e,Z)-isomer	MeSH
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer	MeSH
(9Z,11E)-13-hydroxy-9,11-octadecadienoic acid	SMPDB, HMDB
13-hydroxy-(9Z,11E)-octadeca-9,11-dienoic acid	SMPDB, HMDB
13-hydroxy-9(Z),11(E)-octadecadienoic acid	SMPDB, HMDB
13-hydroxy-9,11-cis,trans-octadecadienoic acid	SMPDB, HMDB
13-hydroxy-9-cis-11-trans-octadecadienoic acid	SMPDB, HMDB
13-hydroxy-cis-9-trans-11-octadecadienoic acid	SMPDB, HMDB
13-hydroxyoctadeca-9,11-dienoic acid	SMPDB, HMDB
13-(Z,E)-HODE	SMPDB, HMDB
13-HODE	SMPDB, MeSH, HMDB
13-hydroxylinoleic acid	SMPDB, HMDB
coriolic acid	SMPDB, ChEBI
(9Z,11E)-13-HODE	SMPDB

Molecular Formula

C₁₈H₃₂O₃

Average Mass

296.451

Monoisotopic Mass

296.23514489

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCC(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+

InChI Key

HNICUWMFWZBIFP-BSZOFBHHSA-N

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:72639 )
Other Octadecanoids (LMFA02000154 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
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	36.53 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fbi-9342100000-19627880cd07ec05cb84	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9670000000-4477cf392a0dbad06305	2017-11-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-9e1599339d026f657237	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h0s-4490000000-00285090bdef0778df6b	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-9510000000-89ebe6c0d089a72cf552	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-91b1f7c0f6e2cc9701fd	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-1090000000-4243ee4d38ebee0073d8	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-8dd86450de60def969ae	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0009726	13-L-Hydroperoxylinoleic acid	Water	Glutathione peroxidase 1		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0112194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4446074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282947

PDB ID

Not Available

ChEBI ID

72639

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (9Z,11E)-13-HODE (MMDBc0000789)

MOL for #<Metabolite:0x000055e8c91c8380>

3D MOL for #<Metabolite:0x000055e8c91c8380>

3D SDF for #<Metabolite:0x000055e8c91c8380>

3D-SDF for #<Metabolite:0x000055e8c91c8380>

PDB for #<Metabolite:0x000055e8c91c8380>

3D PDB for #<Metabolite:0x000055e8c91c8380>

SMILES for #<Metabolite:0x000055e8c91c8380>

INCHI for #<Metabolite:0x000055e8c91c8380>

Structure for #<Metabolite:0x000055e8c91c8380>

3D Structure for #<Metabolite:0x000055e8c91c8380>