MiMeDB: Showing metabocard for 2-hydroxyoctanoic acid (MMDBc0054174)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:57:23 UTC

Update Date

2022-09-01 02:27:40 UTC

Metabolite ID

MMDBc0054174

Metabolite Identification

Common Name

2-hydroxyoctanoic acid

Description

Hydroxyoctanoic acid medium chain substrate of the 2-hydroxy acid oxidases associated with the 3 distinct human 2-hydroxy acid oxidase genes, HAOX1, HAOX2, and HAOX3. (PMID: 10777549 ).

Structure

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

COMPND    HMDB0000711
HETATM    1  C1  UNL     1      -4.540  -0.162  -0.567  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.263   0.523  -0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.065  -0.279  -0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.800   0.407  -0.124  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.436  -0.324  -0.544  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.660   0.421  -0.054  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.938  -0.281  -0.456  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.992  -1.564   0.072  1.00  0.00           O  
HETATM    9  C8  UNL     1       4.062   0.505   0.104  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.266   1.711  -0.198  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.937  -0.083   0.993  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.564  -1.166  -0.143  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.500  -0.252  -1.663  1.00  0.00           H  
HETATM   14  H3  UNL     1      -5.397   0.469  -0.288  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.199   1.559  -0.504  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.290   0.562   0.987  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.143  -1.308  -0.173  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.137  -0.340  -1.682  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.806   0.462   0.976  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.830   1.455  -0.490  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.436  -1.302   0.020  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.492  -0.583  -1.600  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.670   0.480   1.053  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.657   1.439  -0.463  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.077  -0.285  -1.561  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.009  -2.270  -0.608  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.905   0.206   1.083  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

Synonyms

Value	Source
2-Hydroxycaprylic acid	ChEBI
alpha-Hydroxyoctanoic acid	ChEBI
2-Hydroxycaprylate	Generator
a-Hydroxyoctanoate	Generator
a-Hydroxyoctanoic acid	Generator
alpha-Hydroxyoctanoate	Generator
Α-hydroxyoctanoate	Generator
Α-hydroxyoctanoic acid	Generator
Hydroxyoctanoate	Generator
2-Hydroxyoctanoate	HMDB
2-Hydroxyoctanoic acid	HMDB
a-Hydroxy-N-caprylate	HMDB
a-Hydroxy-N-caprylic acid	HMDB
a-Hydroxycaprylate	HMDB
a-Hydroxycaprylic acid	HMDB
alpha-Hydroxy-N-caprylate	HMDB
alpha-Hydroxy-N-caprylic acid	HMDB
alpha-Hydroxycaprylate	HMDB
alpha-Hydroxycaprylic acid	HMDB
DL-2-Hydroxycaprylate	HMDB
DL-2-Hydroxycaprylic acid	HMDB
DL-2-Hydroxyoctanoate	HMDB
DL-2-Hydroxyoctanoic acid	HMDB
alpha-HCA acid	HMDB
2-Hydroxy caprylate	HMDB

Molecular Formula

C₈H₁₆O₃

Average Mass

160.2108

Monoisotopic Mass

160.109944378

IUPAC Name

2-hydroxyoctanoic acid

Traditional Name

hydroxyoctanoate

CAS Registry Number

Not Available

SMILES

CCCCCCC(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)

InChI Key

JKRDADVRIYVCCY-UHFFFAOYSA-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 acid (CHEBI:86543 )
Hydroxy fatty acids (LMFA01050020 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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	18.01 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-890554b11e06b21369e8	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00kr-9140000000-3722662911cf632a3db8	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0900000000-274854495f347923df57	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-01ot-9600000000-8356da50c42e627194d6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0002-9100000000-d73f7a96bae4c293dca5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0900000000-bcfd295851c0251e17a5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-647e329a4f1198a21c4e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-0900000000-9712f63969dfeb7b2b12	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-03di-5900000000-20ecc3e0ff5e821384c2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-14i0-9900000000-808d3e185b47d908aa40	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-bcfd295851c0251e17a5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-647e329a4f1198a21c4e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-8460ae7eec787bc657b1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-5900000000-20ecc3e0ff5e821384c2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-14i0-9900000000-808d3e185b47d908aa40	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-733155aa6e95d717f4b5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0016-9000000000-02dd45597e0b8e26ca84	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0900000000-d8c425a6df077b63af12	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-31f02a63eceeb5fcf92f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-8f4b46f7ea54f38c624a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4j-9000000000-27b166dbd58d56a4f52f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-1da43393b5bc35f7f399	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-ea9909ca4262eb8216a0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07bp-2900000000-c9a1667de6cb3d4c547b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02im-9200000000-8aeb0201ddf350255af6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-1616b530bf1107bb502f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0900-1900000000-5a0164ea551ca57d4d2f	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Saliva

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
MMDBr0017715	2-hydroxyoctanoic acid	2-oxooctanoic acid	L-lactate dehydrogenase (cytochrome)	Dehydrogenation; Oxidation	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
Eukaryota/Fungi	Ascomycota	1
Bacteria	Firmicutes	3	Human ; Human vaginal fluid; Human mucosa; Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0000711

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022197

KNApSAcK ID

Not Available

Chemspider ID

84994

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5679

PubChem Compound

94180

PDB ID

Not Available

ChEBI ID

86543

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. doi: 10.1007/BF01963564. [PubMed:2044590 ]
Jones JM, Morrell JC, Gould SJ: Identification and characterization of HAOX1, HAOX2, and HAOX3, three human peroxisomal 2-hydroxy acid oxidases. J Biol Chem. 2000 Apr 28;275(17):12590-7. doi: 10.1074/jbc.275.17.12590. [PubMed:10777549 ]

Showing metabocard for 2-hydroxyoctanoic acid (MMDBc0054174)

MOL for #<Metabolite:0x000055c79c273620>

3D MOL for #<Metabolite:0x000055c79c273620>

3D SDF for #<Metabolite:0x000055c79c273620>

3D-SDF for #<Metabolite:0x000055c79c273620>

PDB for #<Metabolite:0x000055c79c273620>

3D PDB for #<Metabolite:0x000055c79c273620>

SMILES for #<Metabolite:0x000055c79c273620>

INCHI for #<Metabolite:0x000055c79c273620>

Structure for #<Metabolite:0x000055c79c273620>

3D Structure for #<Metabolite:0x000055c79c273620>