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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:57:13 UTC

Update Date

2023-02-21 17:30:34 UTC

HMDB ID

HMDB0061914

Secondary Accession Numbers

HMDB61914

Metabolite Identification

Common Name

8-Hydroxyoctanoate

Description

8-Hydroxyoctanoate, also known as 8-hydroxycaprylate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 8-Hydroxyoctanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. An omega-hydroxy fatty acid that is caprylic acid in which one of the hydrogens of the terminal methyl group is replaced by a hydroxy group.

Structure

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

COMPND    HMDB0061914
HETATM    1  O1  UNL     1      -2.672   1.605  -0.439  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.452   0.717  -0.082  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.653   1.081   0.548  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.128  -0.698  -0.313  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.720  -0.846  -0.809  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.774  -0.388   0.252  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.694  -0.525  -0.215  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.508  -0.036   0.932  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.974  -0.062   0.825  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.470   0.776  -0.307  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.983   0.290  -1.505  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.664   1.342   1.527  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.283  -1.287   0.643  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.794  -1.173  -1.070  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.553  -0.202  -1.729  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.513  -1.897  -1.118  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.980   0.645   0.529  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.929  -0.996   1.174  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.799   0.057  -1.159  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.830  -1.592  -0.457  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.160  -0.623   1.838  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.107   1.001   1.169  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.431   0.364   1.768  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.407  -1.084   0.738  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.057   1.814  -0.158  1.00  0.00           H  
HETATM   26  H15 UNL     1       4.583   0.822  -0.309  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.112   0.895  -2.271  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   10   23   24
CONECT   10   11   25   26
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
8-Hydroxycaprylic acid	ChEBI
Omega-hydroxycaprylic acid	ChEBI
Omega-hydroxyoctanoic acid	ChEBI
8-Hydroxycaprylate	Generator
Omega-hydroxycaprylate	Generator
Omega-hydroxyoctanoate	Generator
8-Hydroxyoctanoic acid	Generator
8-Hydroxy caprylate	HMDB
8-Hydroxyoctanoate	Generator

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.213

Monoisotopic Molecular Weight

160.109944375

IUPAC Name

8-hydroxyoctanoic acid

Traditional Name

8-hydroxy caprylic acid

CAS Registry Number

Not Available

SMILES

OCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C8H16O3/c9-7-5-3-1-2-4-6-8(10)11/h9H,1-7H2,(H,10,11)

InChI Key

KDMSVYIHKLZKET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Straight chain fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:79162 )
straight-chain fatty acid (CHEBI:79162 )
omega-hydroxy fatty acid (CHEBI:79162 )
Hydroxy fatty acids (LMFA01050023 )

Ontology

Not Available

Feces (PMID: 27015276)

Source

Exogenous

Exogenous (HMDB: HMDB0061914)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	11.9 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.26	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.87	ChemAxon
pKa (Strongest Basic)	-2	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	7	ChemAxon
Refractivity	42.2 m³·mol⁻¹	ChemAxon
Polarizability	18.42 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]+	138.339	31661259
DarkChem	[M-H]-	134.075	31661259
DeepCCS	[M+H]+	141.907	30932474
DeepCCS	[M-H]-	138.86	30932474
DeepCCS	[M-2H]-	175.549	30932474
DeepCCS	[M+Na]+	150.68	30932474
AllCCS	[M+H]+	136.3	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	141.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.15 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8819 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1473.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	364.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	804.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	300.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1019.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	485.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	200.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	208.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyoctanoate	OCCCCCCCC(O)=O	2547.2	Standard polar	33892256
8-Hydroxyoctanoate	OCCCCCCCC(O)=O	1421.8	Standard non polar	33892256
8-Hydroxyoctanoate	OCCCCCCCC(O)=O	1474.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyoctanoate,1TMS,isomer #1	C[Si](C)(C)OCCCCCCCC(=O)O	1536.6	Semi standard non polar	33892256
8-Hydroxyoctanoate,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCCCCO	1487.3	Semi standard non polar	33892256
8-Hydroxyoctanoate,2TMS,isomer #1	C[Si](C)(C)OCCCCCCCC(=O)O[Si](C)(C)C	1622.5	Semi standard non polar	33892256
8-Hydroxyoctanoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCC(=O)O	1766.8	Semi standard non polar	33892256
8-Hydroxyoctanoate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCO	1730.8	Semi standard non polar	33892256
8-Hydroxyoctanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2066.2	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 - 8-Hydroxyoctanoate 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 - 8-Hydroxyoctanoate 10V, Positive-QTOF	splash10-0006-0900000000-bbf993b6f30756b4cc1f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 20V, Positive-QTOF	splash10-002f-4900000000-390efff0304b545a01a5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 40V, Positive-QTOF	splash10-0apl-9000000000-8bbf6035d9987b967ecc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 10V, Negative-QTOF	splash10-0a4i-0900000000-8ec322f719750bdec010	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 20V, Negative-QTOF	splash10-0a4l-1900000000-192978f03f71ec1a17ab	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 40V, Negative-QTOF	splash10-052f-9200000000-4f852e3b502a3081851f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 10V, Negative-QTOF	splash10-0a4i-0900000000-8f1e9e0996ef4a84f05d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 20V, Negative-QTOF	splash10-0a4l-0900000000-08afdc9ddb028302677d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 40V, Negative-QTOF	splash10-0006-9100000000-a6098021d623aa81bafb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 10V, Positive-QTOF	splash10-004m-9300000000-c2e2fd12e52083950ac7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 20V, Positive-QTOF	splash10-0avl-9000000000-82fd5ec26805eccc4080	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyoctanoate 40V, Positive-QTOF	splash10-052g-9000000000-84240c7cdb5a0e85803a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

69820

PDB ID

Not Available

ChEBI ID

79162

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

Not Available

Showing metabocard for 8-Hydroxyoctanoate (HMDB0061914)

MOL for HMDB0061914 (8-Hydroxyoctanoate)

3D MOL for HMDB0061914 (8-Hydroxyoctanoate)

3D SDF for HMDB0061914 (8-Hydroxyoctanoate)

3D-SDF for HMDB0061914 (8-Hydroxyoctanoate)

PDB for HMDB0061914 (8-Hydroxyoctanoate)

3D PDB for HMDB0061914 (8-Hydroxyoctanoate)

SMILES for HMDB0061914 (8-Hydroxyoctanoate)

INCHI for HMDB0061914 (8-Hydroxyoctanoate)

Structure for HMDB0061914 (8-Hydroxyoctanoate)

3D Structure for HMDB0061914 (8-Hydroxyoctanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra