NP-MRD: Showing NP-Card for (R)-3-Hydroxyoctanoic acid (NP0086519)

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Record Information

Version

2.0

Created at

2022-05-11 16:23:07 UTC

Updated at

2022-05-11 16:23:07 UTC

NP-MRD ID

NP0086519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-3-Hydroxyoctanoic acid

Description

(R)-3-Hydroxyoctanoic acid, also known as (R)-3-OH-caprylic acid or (R)-3-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 (R)-3-Hydroxyoctanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxyoctanoic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, (R)-3-hydroxyoctanoic acid participates in a number of enzymatic reactions. In particular, (R)-3-hydroxyoctanoic acid can be biosynthesized from 3-oxooctanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-hydroxyoctanoic acid can be converted into trans-2-octenoic acid through the action of the enzyme fatty acid synthase. Dyhydrase domain. In humans, (R)-3-hydroxyoctanoic acid is involved in fatty acid biosynthesis. Outside of the human body, (R)-3-Hydroxyoctanoic acid has been detected, but not quantified in, fruits and milk and milk products. This could make (R)-3-hydroxyoctanoic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 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

View in JSmol

Synonyms

Value	Source
(R)-3-Hydroxyoctanoate	Generator
(3R)-3-Hydroxy-octanoic acid	HMDB
(R)-3-Hydroxycaprylic acid	HMDB
(R)-3-OH Octanoic acid	HMDB
(R)-3-OH-Caprylic acid	HMDB
(R)-beta-Hydroxycaprylic acid	HMDB
(R)-beta-Hydroxyoctanoic acid	HMDB
(R)-beta-OH-Caprylic acid	HMDB
(R)-beta-OH-Octanoic acid	HMDB
(3R)-3-Hydroxy-octanoate	HMDB
(R)-3-Hydroxycaprylate	HMDB
(R)-3-OH Octanoate	HMDB
(R)-3-OH-Caprylate	HMDB
(R)-b-Hydroxycaprylate	HMDB
(R)-b-Hydroxycaprylic acid	HMDB
(R)-beta-Hydroxycaprylate	HMDB
(R)-Β-hydroxycaprylate	HMDB
(R)-Β-hydroxycaprylic acid	HMDB
(R)-b-Hydroxyoctanoate	HMDB
(R)-b-Hydroxyoctanoic acid	HMDB
(R)-beta-Hydroxyoctanoate	HMDB
(R)-Β-hydroxyoctanoate	HMDB
(R)-Β-hydroxyoctanoic acid	HMDB
(R)-b-OH-Caprylate	HMDB
(R)-b-OH-Caprylic acid	HMDB
(R)-beta-OH-Caprylate	HMDB
(R)-Β-OH-caprylate	HMDB
(R)-Β-OH-caprylic acid	HMDB
(R)-b-OH-Octanoate	HMDB
(R)-b-OH-Octanoic acid	HMDB
(R)-beta-OH-Octanoate	HMDB
(R)-Β-OH-octanoate	HMDB
(R)-Β-OH-octanoic acid	HMDB

Chemical Formula

C₈H₁₆O₃

Average Mass

160.2108 Da

Monoisotopic Mass

160.10994 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0010722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (R)-3-Hydroxyoctanoic acid (NP0086519)

MOL for NP0086519 ((R)-3-Hydroxyoctanoic acid)

3D MOL for NP0086519 ((R)-3-Hydroxyoctanoic acid)

3D SDF for NP0086519 ((R)-3-Hydroxyoctanoic acid)

3D-SDF for NP0086519 ((R)-3-Hydroxyoctanoic acid)

PDB for NP0086519 ((R)-3-Hydroxyoctanoic acid)

3D PDB for NP0086519 ((R)-3-Hydroxyoctanoic acid)

SMILES for NP0086519 ((R)-3-Hydroxyoctanoic acid)

INCHI for NP0086519 ((R)-3-Hydroxyoctanoic acid)

Structure for NP0086519 ((R)-3-Hydroxyoctanoic acid)

3D Structure for NP0086519 ((R)-3-Hydroxyoctanoic acid)