MiMeDB: Showing metabocard for 3-Hydroxyoctadecanoic acid (MMDBc0006529)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:41:48 UTC

Update Date

2025-10-07 16:05:11 UTC

Metabolite ID

MMDBc0006529

Metabolite Identification

Common Name

3-Hydroxyoctadecanoic acid

Description

3-Hydroxyoctadecanoic acid is a member of the hydroxy fatty acid chemical class, characterized by the presence of a hydroxyl group on the third carbon of an 18-carbon chain. This metabolite has garnered attention in biomedical research, particularly in studies involving lipid structures and microbial metabolism. For instance, it has been identified in lipid A structures derived from Helicobacter pylori, where it plays a role in the acylation of glucosamine disaccharides (PMID:12473106 ). Additionally, 3-hydroxyoctadecanoic acid has been included in analytical methods for quantifying various 3-hydroxy fatty acids, showcasing its relevance in metabolic studies (PMID:26818235 ). Research has also demonstrated the potential of utilizing palm oil as a substrate for the production of polyhydroxyalkanoates, which can incorporate short-chain and long-chain hydroxy fatty acids, including 3-hydroxyoctadecanoic acid (PMID:15322031 ). These findings underscore the compound's significance in both biochemical pathways and industrial applications, highlighting its versatility and importance in the study of fatty acid metabolism and microbial bioprocessing.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251503552D          

 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
   19.9026    4.8908    0.0000 O   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
   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  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  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
 13 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006529

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCC(O)CC(O)=O

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

> <INCHI_KEY>
POMQYTSPMKEQNB-UHFFFAOYSA-N

> <FORMULA>
C18H36O3

> <MOLECULAR_WEIGHT>
300.483

> <EXACT_MASS>
300.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.142515716932124

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxyoctadecanoic acid

> <ALOGPS_LOGP>
6.83

> <JCHEM_LOGP>
5.914909040666667

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.80109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyoctadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         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  O   UNK     0      37.152   9.129   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+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+0
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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

Synonyms

Value	Source
3-Hydroxystearic acid	ChEBI
3-Hydroxystearate	Generator
3-Hydroxyoctadecanoate	Generator
DL-3-Hydroxy stearate	Generator

Molecular Formula

C₁₈H₃₆O₃

Average Mass

300.483

Monoisotopic Mass

300.266445019

IUPAC Name

3-hydroxyoctadecanoic acid

Traditional Name

3-hydroxyoctadecanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(O)CC(O)=O

InChI Identifier

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

InChI Key

POMQYTSPMKEQNB-UHFFFAOYSA-N

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
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy monocarboxylic acid (CHEBI:50578 )
Other Octadecanoids (LMFA02000121 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	6.83	ALOGPS
logP	5.91	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	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	16	ChemAxon
Refractivity	87.8 m³·mol⁻¹	ChemAxon
Polarizability	39.14 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)	2025-10-23	208.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	40.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	575.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	823.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	889.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	467.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2935.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	109.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	301.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	688.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	394.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	217.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	217.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	10.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	532.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	535.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	457.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1788.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1837.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_1	CCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C	standard non polar	2025-10-23	1803.49
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_2	CCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2270.51
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_3	CCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-23	2025.88
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_1	CCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C	standard polar	2025-10-23	1975.54
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_2	CCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C	standard polar	2025-10-23	1642.01
Gas Chromatography	3-Hydroxyoctadecanoic acid_TMS_3	CCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-23	1499.87

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

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		Metabolic reconstruction

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

50578

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3-Hydroxyoctadecanoic acid (MMDBc0006529)

MOL for #<Metabolite:0x00007f9acd016700>

3D MOL for #<Metabolite:0x00007f9acd016700>

3D SDF for #<Metabolite:0x00007f9acd016700>

3D-SDF for #<Metabolite:0x00007f9acd016700>

PDB for #<Metabolite:0x00007f9acd016700>

3D PDB for #<Metabolite:0x00007f9acd016700>

SMILES for #<Metabolite:0x00007f9acd016700>

INCHI for #<Metabolite:0x00007f9acd016700>

Structure for #<Metabolite:0x00007f9acd016700>

3D Structure for #<Metabolite:0x00007f9acd016700>