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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2021-09-14 15:47:11 UTC

HMDB ID

HMDB0002264

Secondary Accession Numbers

HMDB02264

Metabolite Identification

Common Name

(R)-2-Hydroxycaprylic acid

Description

(R)-2-Hydroxycaprylic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review very few articles have been published on (R)-2-Hydroxycaprylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0002264
HETATM    1  C1  UNL     1       3.832   0.295   0.967  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.489  -0.209   0.428  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.092   0.791  -0.641  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.779   0.398  -1.259  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.359   0.340  -0.272  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.632  -0.051  -0.976  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.826  -0.136  -0.100  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.928  -0.510  -0.908  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.730  -1.041   1.037  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.836  -0.901   1.907  1.00  0.00           O  
HETATM   11  O3  UNL     1      -3.617  -2.095   1.209  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.402   0.692   0.113  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.412  -0.535   1.418  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.583   1.079   1.714  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.771  -0.246   1.254  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.679  -1.191  -0.023  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.892   0.871  -1.404  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.940   1.809  -0.175  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.939  -0.569  -1.777  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.529   1.130  -2.064  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.408   1.288   0.266  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.069  -0.460   0.467  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.430  -1.040  -1.464  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.802   0.657  -1.811  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.091   0.875   0.284  1.00  0.00           H  
HETATM   26  H15 UNL     1      -4.595  -0.954  -0.317  1.00  0.00           H  
HETATM   27  H16 UNL     1      -4.018  -2.252   2.127  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-2-Hydroxycaprylate	Generator
(R)-2-Hydroxyoctanoate	HMDB
(R)-2-Hydroxyoctanoic acid	HMDB
(R)-a-Hydroxycaprylate	HMDB
(R)-a-Hydroxycaprylic acid	HMDB
(R)-alpha-Hydroxycaprylate	HMDB
(R)-alpha-Hydroxycaprylic acid	HMDB
2-Hydroxy-D-octanoate	HMDB
2-Hydroxy-D-octanoic acid	HMDB
2-Hydroxy-delta-octanoate	HMDB
2-Hydroxy-delta-octanoic acid	HMDB
D-2-Hydroxyoctanoate	HMDB
D-2-Hydroxyoctanoic acid	HMDB
delta-2-Hydroxyoctanoate	HMDB
delta-2-Hydroxyoctanoic acid	HMDB
2R-Hydroxy-octanoate	Generator, HMDB

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

(2R)-2-hydroxyoctanoic acid

Traditional Name

D-2-hydroxyoctanoic acid

CAS Registry Number

30117-44-3

SMILES

CCCCCC[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m1/s1

InChI Key

JKRDADVRIYVCCY-SSDOTTSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050313 )

Ontology

Not Available

Feces (PMID: 27275383)
Urine (HMDB: HMDB0002264)

Cellular substructure

Cytoplasm (HMDB: HMDB0002264)
Cell membrane (HMDB: HMDB0002264)

Organelle

Adiposome (HMDB: HMDB0002264)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002264)

Source

Endogenous

Endogenous (HMDB: HMDB0002264)

Animal

Animal (HMDB: HMDB0002264)

Exogenous

Food

Food (HMDB: HMDB0002264)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002264)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002264)

Lipid metabolism pathway (HMDB: HMDB0002264)

Biochemical process

Lipid transport (HMDB: HMDB0002264)

Role

Biological role

Energy source (HMDB: HMDB0002264)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.2 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.83	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	-3.8	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	6	ChemAxon
Refractivity	41.77 m³·mol⁻¹	ChemAxon
Polarizability	18.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.904	31661259
DarkChem	[M-H]-	136.175	31661259
DeepCCS	[M+H]+	138.179	30932474
DeepCCS	[M-H]-	134.262	30932474
DeepCCS	[M-2H]-	171.729	30932474
DeepCCS	[M+Na]+	147.07	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.5	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	136.7	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-2-Hydroxycaprylic acid	CCCCCC[C@@H](O)C(O)=O	2163.2	Standard polar	33892256
(R)-2-Hydroxycaprylic acid	CCCCCC[C@@H](O)C(O)=O	1273.7	Standard non polar	33892256
(R)-2-Hydroxycaprylic acid	CCCCCC[C@@H](O)C(O)=O	1340.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-2-Hydroxycaprylic acid,1TMS,isomer #1	CCCCCC[C@@H](O[Si](C)(C)C)C(=O)O	1406.1	Semi standard non polar	33892256
(R)-2-Hydroxycaprylic acid,1TMS,isomer #2	CCCCCC[C@@H](O)C(=O)O[Si](C)(C)C	1333.4	Semi standard non polar	33892256
(R)-2-Hydroxycaprylic acid,2TMS,isomer #1	CCCCCC[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1458.9	Semi standard non polar	33892256
(R)-2-Hydroxycaprylic acid,1TBDMS,isomer #1	CCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1626.5	Semi standard non polar	33892256
(R)-2-Hydroxycaprylic acid,1TBDMS,isomer #2	CCCCCC[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1560.8	Semi standard non polar	33892256
(R)-2-Hydroxycaprylic acid,2TBDMS,isomer #1	CCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1910.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxycaprylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-890554b11e06b21369e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxycaprylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00kr-9140000000-3722662911cf632a3db8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxycaprylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 10V, Positive-QTOF	splash10-01ox-0900000000-6593e0937f6ec62d47ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 20V, Positive-QTOF	splash10-00ku-9800000000-2ee8087a7bc4c5a7a1a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 40V, Positive-QTOF	splash10-052f-9000000000-e4e087704c73cc1a9643	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-ea9909ca4262eb8216a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 20V, Negative-QTOF	splash10-07bp-2900000000-c9a1667de6cb3d4c547b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 40V, Negative-QTOF	splash10-02im-9200000000-8aeb0201ddf350255af6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-1616b530bf1107bb502f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 20V, Negative-QTOF	splash10-0900-1900000000-5a0164ea551ca57d4d2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 40V, Negative-QTOF	splash10-0006-9000000000-b05a5cabfbd457c9a0cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 10V, Positive-QTOF	splash10-0ap1-9200000000-1e87c3f8d09f7ccca821	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 20V, Positive-QTOF	splash10-052f-9000000000-2968ffe0d95bc4c5477c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxycaprylic acid 40V, Positive-QTOF	splash10-052f-9000000000-2c1b8a8f530ee430c2b7	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022934

KNApSAcK ID

Not Available

Chemspider ID

4472285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6582

PubChem Compound

5312860

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ki KR, Lee J, Ha D, Kim JH: Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography. J Chromatogr A. 2000 Sep 8;891(2):257-66. [PubMed:11043786 ]

Showing metabocard for (R)-2-Hydroxycaprylic acid (HMDB0002264)

MOL for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

3D MOL for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

3D SDF for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

3D-SDF for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

PDB for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

3D PDB for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

SMILES for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

INCHI for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

Structure for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

3D Structure for HMDB0002264 ((R)-2-Hydroxycaprylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra