MiMeDB: Showing metabocard for 2-hydroxyoctadecanoic acid (MMDBc0055249)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:47:20 UTC

Update Date

2025-10-07 16:04:19 UTC

Metabolite ID

MMDBc0055249

Metabolite Identification

Common Name

2-hydroxyoctadecanoic acid

Description

2-hydroxyoctadecanoic acid is a fatty acid derivative belonging to the class of hydroxy fatty acids. Its chemical structure features a hydroxyl group at the second carbon of the octadecanoic acid chain, which influences its physical and chemical properties. This metabolite is involved in various biochemical pathways, including the synthesis of lipodepsipeptides such as Ralstonins, which are produced by bacteria and regulated through quorum sensing mechanisms (PMID:28753290 ). Additionally, studies have explored the behavior of 2-hydroxyoctadecanoic acid in nonequilibrium monolayers, particularly in relation to biomineralization processes involving calcium carbonate (PMID:21417341 ). The degradation pathways of this lipid class have also been investigated, utilizing both labeled and unlabeled forms of the acid (PMID:15644336 ). Furthermore, its presence is noted in ceramide analysis, where it appears alongside phytosphingosines, indicating its role in sphingolipid metabolism (PMID:12626405 ). Changes in the levels of 2-hydroxyoctadecanoic acid have been observed in differentiating tissues, suggesting its involvement in developmental processes (PMID:15055237 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221472D          

 21 20  0  0  0  0            999 V2000
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  CHG  1  21  -1
M  END
> <DATABASE_ID>
MMDBc0055249

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCCC(O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h17,19H,2-16H2,1H3,(H,20,21)/p-1

> <INCHI_KEY>
KIHBGTRZFAVZRV-UHFFFAOYSA-M

> <FORMULA>
C18H35O3

> <MOLECULAR_WEIGHT>
299.476

> <EXACT_MASS>
299.259168567

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.93541093452111

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyoctadecanoate

> <JCHEM_LOGP>
6.274654187

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148890034412

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.255557640559995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528712514443

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
98.61489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxyoctadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      38.485  12.979   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      39.819   9.129   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
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                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

Synonyms

Value	Source
2-OH-C18:0(1-)	ChEBI
alpha-Hydroxyoctadecanoate	ChEBI
alpha-Hydroxystearate	ChEBI
a-Hydroxyoctadecanoate	Generator
a-Hydroxyoctadecanoic acid	Generator
alpha-Hydroxyoctadecanoic acid	Generator
Α-hydroxyoctadecanoate	Generator
Α-hydroxyoctadecanoic acid	Generator
a-Hydroxystearate	Generator
a-Hydroxystearic acid	Generator
alpha-Hydroxystearic acid	Generator
Α-hydroxystearate	Generator
Α-hydroxystearic acid	Generator
2-Hydroxystearic acid	Generator

Molecular Formula

C₁₈H₃₅O₃

Average Mass

299.476

Monoisotopic Mass

299.259168567

IUPAC Name

2-hydroxyoctadecanoate

Traditional Name

2-hydroxyoctadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC(O)C([O-])=O

InChI Identifier

InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h17,19H,2-16H2,1H3,(H,20,21)/p-1

InChI Key

KIHBGTRZFAVZRV-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Monosaccharide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid anion (CHEBI:76724 )
2-hydroxy fatty acid anion (CHEBI:76724 )
a small molecule (S-2-HYDROXYSTEARATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	6.27	ChemAxon
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	98.61 m³·mol⁻¹	ChemAxon
Polarizability	38.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	196.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	39.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	634.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1096.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1077.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	732.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3285.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	116.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	422.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	847.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	616.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	395.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	278.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	773.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	603.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	564.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2085.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2325.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2-hydroxyoctadecanoic acid_TMS_1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)[O-]	standard non polar	2025-10-24	1565.56
Gas Chromatography	2-hydroxyoctadecanoic acid_TMS_1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)[O-]	standard polar	2025-10-24	2432.27

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0039068	Octadecanoate (N-C18:0)	2-hydroxyoctadecanoic acid	Fatty-acid peroxygenase	Hydroxylation	RHEA	34755880

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
Bacteria/Eubacteria	Firmicutes	2	Human ; Human vaginal fluid; Human mucosa; Human feces
Bacteria/Eubacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13600149

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21993177

PDB ID

Not Available

ChEBI ID

76724

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-hydroxyoctadecanoic acid (MMDBc0055249)

MOL for #<Metabolite:0x00007f9ad01176b0>

3D MOL for #<Metabolite:0x00007f9ad01176b0>

3D SDF for #<Metabolite:0x00007f9ad01176b0>

3D-SDF for #<Metabolite:0x00007f9ad01176b0>

PDB for #<Metabolite:0x00007f9ad01176b0>

3D PDB for #<Metabolite:0x00007f9ad01176b0>

SMILES for #<Metabolite:0x00007f9ad01176b0>

INCHI for #<Metabolite:0x00007f9ad01176b0>

Structure for #<Metabolite:0x00007f9ad01176b0>

3D Structure for #<Metabolite:0x00007f9ad01176b0>