MiMeDB: Showing metabocard for (R)-3-Hydroxyoctanoic acid (MMDBc0047808)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:43:40 UTC

Update Date

2022-09-01 01:59:25 UTC

Metabolite ID

MMDBc0047808

Metabolite Identification

Common Name

(R)-3-Hydroxyoctanoic acid

Description

(R)-3-Hydroxyoctanoic acid, also known as (R)-3-OH-caprylic acid or (3R)-3-hydroxy-octanoate, 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 (R)-3-Hydroxyoctanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, (R)-3-hydroxyoctanoic acid is involved in the fatty acid biosynthesis pathway (R)-3-Hydroxyoctanoic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), fruits, and milk and milk products. This could make (R)-3-hydroxyoctanoic acid a potential biomarker for the consumption of these foods (R)-3-Hydroxyoctanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (R)-3-Hydroxyoctanoic acid.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      23.093 -14.182   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      23.093 -12.654   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.427 -14.952   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.110 -14.182   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.444 -14.952   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.778 -14.182   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.101 -14.952   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.425 -14.182   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.759 -14.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.776 -14.952   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.328 -12.941   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      21.405 -12.974   0.000  0.00  0.00           H+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5   10                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11   12                                             
CONECT    9    8    1                                                       
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0010722
HETATM    1  C1  UNL     1      -2.816   1.897  -0.093  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.154   0.610  -0.526  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.803  -0.225   0.703  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.140  -1.509   0.280  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.129  -1.295  -0.491  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.188  -0.553   0.252  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.620  -1.133   1.410  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.332  -0.283  -0.702  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.437   0.448  -0.079  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.284  -0.147   0.622  1.00  0.00           O  
HETATM   11  O3  UNL     1       3.572   1.820  -0.250  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.313   2.333  -0.992  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.016   2.585   0.292  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.555   1.650   0.685  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.836   0.078  -1.194  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.248   0.887  -1.105  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.246   0.362   1.424  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.773  -0.512   1.168  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.979  -2.183   1.133  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.851  -2.023  -0.404  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.532  -2.320  -0.719  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.077  -0.751  -1.435  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.754   0.449   0.525  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.934  -1.452   2.010  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.884   0.264  -1.567  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.676  -1.287  -1.054  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.463   2.290  -0.384  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
(3R)-3-Hydroxy-octanoic acid	ChEBI
(R)-3-Hydroxycaprylic acid	ChEBI
(R)-3-OH Octanoic acid	ChEBI
(R)-3-OH-Caprylic acid	ChEBI
(R)-beta-Hydroxycaprylic acid	ChEBI
(R)-beta-Hydroxyoctanoic acid	ChEBI
(R)-beta-OH-Caprylic acid	ChEBI
(R)-beta-OH-Octanoic acid	ChEBI
(3R)-3-Hydroxy-octanoate	Generator
(R)-3-Hydroxycaprylate	Generator
(R)-3-OH Octanoate	Generator
(R)-3-OH-Caprylate	Generator
(R)-b-Hydroxycaprylate	Generator
(R)-b-Hydroxycaprylic acid	Generator
(R)-beta-Hydroxycaprylate	Generator
(R)-Β-hydroxycaprylate	Generator
(R)-Β-hydroxycaprylic acid	Generator
(R)-b-Hydroxyoctanoate	Generator
(R)-b-Hydroxyoctanoic acid	Generator
(R)-beta-Hydroxyoctanoate	Generator
(R)-Β-hydroxyoctanoate	Generator
(R)-Β-hydroxyoctanoic acid	Generator
(R)-b-OH-Caprylate	Generator
(R)-b-OH-Caprylic acid	Generator
(R)-beta-OH-Caprylate	Generator
(R)-Β-OH-caprylate	Generator
(R)-Β-OH-caprylic acid	Generator
(R)-b-OH-Octanoate	Generator
(R)-b-OH-Octanoic acid	Generator
(R)-beta-OH-Octanoate	Generator
(R)-Β-OH-octanoate	Generator
(R)-Β-OH-octanoic acid	Generator
(R)-3-Hydroxyoctanoate	Generator

Molecular Formula

C₈H₁₆O₃

Average Mass

160.2108

Monoisotopic Mass

160.109944378

IUPAC Name

(3R)-3-hydroxyoctanoic acid

Traditional Name

(R)-3-hydroxyoctanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CCCCC)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-/m1/s1

InChI Key

NDPLAKGOSZHTPH-SSDOTTSWSA-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:37099 )
(3R)-3-hydroxy fatty acid (CHEBI:37099 )
Hydroxy fatty acids (LMFA01050314 )

Functional Ontology

Not Available

Physical Properties

State

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	18.14 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	splash10-052o-9200000000-43d57763d2a30e89979b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ri-9350000000-f1efc144e4aa8ba19a72	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1900000000-e5cda5e57d0fb350dc6e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002g-8900000000-206c3ff570d17b537e39	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-c32a98aa8083b6459b4a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2900000000-9112efe71e9f56f43bab	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aos-8900000000-f482349594658282b6e5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9100000000-b0b3f7b33ed057654f96	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zna-9400000000-ba19979661ce66d42c47	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-7a423069bad50c00a0fd	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9000000000-7c89cf68b731953f3797	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4l-3900000000-ef763a7f3b584b771412	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-9100000000-9b510a15a343a9e2d365	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-05f3a26a1fda3e795cba	2021-09-23	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

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
MMDBp0191709	Fatty acid synthase	Enzyme	P49327	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0010722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010907

KNApSAcK ID

Not Available

Chemspider ID

4472286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312861

PDB ID

Not Available

ChEBI ID

37099

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for (R)-3-Hydroxyoctanoic acid (MMDBc0047808)

MOL for #<Metabolite:0x00007fdb4c8f8408>

3D MOL for #<Metabolite:0x00007fdb4c8f8408>

3D SDF for #<Metabolite:0x00007fdb4c8f8408>

3D-SDF for #<Metabolite:0x00007fdb4c8f8408>

PDB for #<Metabolite:0x00007fdb4c8f8408>

3D PDB for #<Metabolite:0x00007fdb4c8f8408>

SMILES for #<Metabolite:0x00007fdb4c8f8408>

INCHI for #<Metabolite:0x00007fdb4c8f8408>

Structure for #<Metabolite:0x00007fdb4c8f8408>

3D Structure for #<Metabolite:0x00007fdb4c8f8408>