AFCDB: (R)-3-Hydroxy-hexadecanoic acid (FDB027881)

Record Information

Version

1.0

Creation date

2011-09-21 01:31:22 UTC

Update date

2017-04-03 05:02:17 UTC

Primary ID

FDB027881

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-3-Hydroxy-hexadecanoic acid

Description

(R)-3-Hydroxy-hexadecanoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms (R)-3-Hydroxy-hexadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

2398-34-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	5.75	ALOGPS
logP	5.03	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.67	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	14	ChemAxon
Refractivity	78.6 m³·mol⁻¹	ChemAxon
Polarizability	35.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H32O3

IUPAC name

(3R)-3-hydroxyhexadecanoic acid

InChI Identifier

InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1

InChI Key

CBWALJHXHCJYTE-OAHLLOKOSA-N

Isomeric SMILES

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

Average Molecular Weight

272.4235

Monoisotopic Molecular Weight

272.23514489

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(3R)-3-hydroxy fatty acid (CHEBI:38247 )
3-hydroxypalmitic acid (CHEBI:38247 )
Hydroxy fatty acids (LMFA01050366 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(R)-3-Hydroxy-hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9340000000-7f3268f819048bc0fb4c	Spectrum
Predicted GC-MS	(R)-3-Hydroxy-hexadecanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009i-9231100000-2ee529fc9d520d001aee	Spectrum
Predicted GC-MS	(R)-3-Hydroxy-hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-3-Hydroxy-hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0090000000-170f4b78f38f50653281	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3590000000-72735537a44743fc49f3	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-18c6bb5829efbdfd8324	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-69dd00738d6e82b5a71a	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-2090000000-a29b15501f484eac1a95	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-34c29dc88bb32e93e509	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1090000000-b8b5369541b20493e1ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9020000000-0763938b2406df6b3db3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9020000000-405e88be7cf7e93b3269	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-2190000000-13586bde632215e51549	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9430000000-96b8600a3183721e0024	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-ac851687758f1e0f9afd	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

21865352

ChEMBL ID

CHEMBL2207728

KEGG Compound ID

Not Available

Pubchem Compound ID

15569776

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB10734

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Fatty acid synthase	FASN	P49327
3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial	OXSM	Q9NWU1

Pathways

Name	SMPDB Link	KEGG Link
Fatty Acid Biosynthesis	SMP00456	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

(R)-3-Hydroxy-hexadecanoic acid (FDB027881)

Structure for FDB027881 ((R)-3-Hydroxy-hexadecanoic acid)