MiMeDB: Showing metabocard for 3-Hydroxyoctanoic acid (MMDBc0000398)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:52 UTC

Update Date

2024-04-30 19:32:09 UTC

Metabolite ID

MMDBc0000398

Metabolite Identification

Common Name

3-Hydroxyoctanoic acid

Description

3-Hydroxyoctanoic acid (CAS: 14292-27-4) is an organic 3-hydroxy dicarboxylic acid, a metabolite of medium-chain fatty acid oxidation found in human urine. It is believed that urinary 3-hydroxy dicarboxylic acids are derived from the omega-oxidation of 3-hydroxy fatty acids and the subsequent beta-oxidation of longer-chain 3-hydroxy dicarboxylic acids. (PMID:1870421 ). 3-Hydroxyoctanoic acid has been identified in the human placenta (PMID: 32033212 ).

Structure

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

COMPND    HMDB0001954
HETATM    1  C1  UNL     1      -3.342   0.715   0.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.524  -0.518  -0.215  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.383  -0.145  -1.135  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.457   0.860  -0.499  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.175   0.382   0.764  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.009  -0.853   0.596  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.561  -1.230   1.817  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.102  -0.727  -0.408  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.082   0.326  -0.110  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.013   1.060   0.906  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.149   0.555  -0.966  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.412   0.460   0.265  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.998   1.172   1.087  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.241   1.432  -0.705  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.209  -1.205  -0.750  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.161  -1.027   0.705  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.869  -1.066  -1.455  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.832   0.340  -2.027  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.104   1.741  -0.221  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.285   1.257  -1.208  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.711   1.222   1.227  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.660   0.128   1.473  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.357  -1.701   0.270  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.390  -1.757   1.716  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.642  -1.713  -0.422  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.688  -0.633  -1.451  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.024   0.927  -0.632  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    8   23
CONECT    7   24
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   11   27
END

Synonyms

Value	Source
(3S)-3-Hydroxy-octanoic acid	ChEBI
(S)-3-Hydroxycaprylic acid	ChEBI
(S)-3-OH Octanoic acid	ChEBI
(S)-3-OH-Caprylic acid	ChEBI
(S)-beta-Hydroxycaprylic acid	ChEBI
(S)-beta-Hydroxyoctanoic acid	ChEBI
(S)-beta-OH-Caprylic acid	ChEBI
(S)-beta-OH-Octanoic acid	ChEBI
(3S)-3-Hydroxy-octanoate	Generator
(S)-3-Hydroxycaprylate	Generator
(S)-3-OH Octanoate	Generator
(S)-3-OH-Caprylate	Generator
(S)-b-Hydroxycaprylate	Generator
(S)-b-Hydroxycaprylic acid	Generator
(S)-beta-Hydroxycaprylate	Generator
(S)-Β-hydroxycaprylate	Generator
(S)-Β-hydroxycaprylic acid	Generator
(S)-b-Hydroxyoctanoate	Generator
(S)-b-Hydroxyoctanoic acid	Generator
(S)-beta-Hydroxyoctanoate	Generator
(S)-Β-hydroxyoctanoate	Generator
(S)-Β-hydroxyoctanoic acid	Generator
(S)-b-OH-Caprylate	Generator
(S)-b-OH-Caprylic acid	Generator
(S)-beta-OH-Caprylate	Generator
(S)-Β-OH-caprylate	Generator
(S)-Β-OH-caprylic acid	Generator
(S)-b-OH-Octanoate	Generator
(S)-b-OH-Octanoic acid	Generator
(S)-beta-OH-Octanoate	Generator
(S)-Β-OH-octanoate	Generator
(S)-Β-OH-octanoic acid	Generator
3-Hydroxyoctanoate	Generator
(S)-3-Hydroxyoctanoate	HMDB
3-Hydroxyoctanoic acid, (S)-isomer	HMDB
(3S)-3-Hydroxyoctanoate	HMDB
(3S)-3-Hydroxyoctanoic acid	HMDB
(±)-3-hydroxyoctanoate	HMDB
(±)-3-hydroxyoctanoic acid	HMDB
3-Hydroxycaprylate	HMDB
3-Hydroxycaprylic acid	HMDB
FA(8:0(3-OH))	HMDB
FA(8:0(3S-OH))	HMDB
S-3-Hydroxyoctanoate	HMDB
S-3-Hydroxyoctanoic acid	HMDB
beta-Hydroxycaprylate	HMDB
beta-Hydroxycaprylic acid	HMDB
beta-Hydroxyoctanoate	HMDB
beta-Hydroxyoctanoic acid	HMDB
Β-hydroxycaprylate	HMDB
Β-hydroxycaprylic acid	HMDB
Β-hydroxyoctanoate	HMDB
Β-hydroxyoctanoic acid	HMDB
3-Hydroxyoctanoic acid	MeSH

Molecular Formula

C₈H₁₆O₃

Average Mass

160.2108

Monoisotopic Mass

160.109944378

IUPAC Name

(3S)-3-hydroxyoctanoic acid

Traditional Name

(S)-3-hydroxyoctanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)CC(O)=O

InChI Identifier

InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m0/s1

InChI Key

NDPLAKGOSZHTPH-ZETCQYMHSA-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
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
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

3-hydroxyoctanoic acid (CHEBI:37100 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	13.6 g/L	ALOGPS
logP	1.44	ALOGPS
logP	1.47	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.84	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	6	ChemAxon
Refractivity	41.79 m³·mol⁻¹	ChemAxon
Polarizability	17.97 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
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00ov-5920000000-2c7ce12b4e2e186a597f	2019-10-24	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ov-5920000000-2c7ce12b4e2e186a597f	2019-10-24	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-4900000000-fd08cd8b97f656038b55	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-ad1d87402b7f1e589172	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-191e4c2a7ad7ea5541dd	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0odj-9500000000-95cc4658f3be66a2d9aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-2701ee861eb39af89635	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e9a7bc1b045535fb0dbb	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Placenta

Tissue Locations

Placenta

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
Acylcarnitine 3-hydroxyoctanoylcarnitine

Metabolic Reactions

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
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified		3	2400	uM	Children (1-13 years old)	Male	3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency	HMDB	9337379
Human Blood	Detected and Quantified	20			uM	Adult (>18 years old)	Male	Normal	HMDB	9337379
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0001954

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022761

KNApSAcK ID

Not Available

Chemspider ID

9542083

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Hydroxyoctanoic acid

METLIN ID

Not Available

PubChem Compound

11367166

PDB ID

Not Available

ChEBI ID

37100

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. doi: 10.1177/000456329202900509. [PubMed:1444166 ]
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. doi: 10.1016/0026-0495(91)90083-9. [PubMed:1870421 ]
Montgomery JA, Mamer OA, Colle E: Profiles in altered metabolism. IV--Induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat. Biomed Environ Mass Spectrom. 1989 Jun;18(6):416-23. doi: 10.1002/bms.1200180610. [PubMed:2765701 ]
Kelley RI, Morton DH: 3-Hydroxyoctanoic aciduria: identification of a new organic acid in the urine of a patient with non-ketotic hypoglycemia. Clin Chim Acta. 1988 Jun 30;175(1):19-26. doi: 10.1016/0009-8981(88)90031-9. [PubMed:3168281 ]
Jones PM, Butt Y, Bennett MJ: Accumulation of 3-hydroxy-fatty acids in the culture medium of long-chain L-3-hydroxyacyl CoA dehydrogenase (LCHAD) and mitochondrial trifunctional protein-deficient skin fibroblasts: implications for medium chain triglyceride dietary treatment of LCHAD deficiency. Pediatr Res. 2003 May;53(5):783-7. doi: 10.1203/01.PDR.0000059748.67987.1F. Epub 2003 Mar 5. [PubMed:12621125 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 3-Hydroxyoctanoic acid (MMDBc0000398)

MOL for #<Metabolite:0x00007fdb11365170>

3D MOL for #<Metabolite:0x00007fdb11365170>

3D SDF for #<Metabolite:0x00007fdb11365170>

3D-SDF for #<Metabolite:0x00007fdb11365170>

PDB for #<Metabolite:0x00007fdb11365170>

3D PDB for #<Metabolite:0x00007fdb11365170>

SMILES for #<Metabolite:0x00007fdb11365170>

INCHI for #<Metabolite:0x00007fdb11365170>

Structure for #<Metabolite:0x00007fdb11365170>

3D Structure for #<Metabolite:0x00007fdb11365170>