Showing Compound Hexadecanedioic acid (FDB003049)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:38 UTC

Update date

2020-09-17 15:38:39 UTC

Primary ID

FDB003049

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hexadecanedioic acid

Description

Hexadecanedioic acid, also known as 1,16-hexadecanedioate or thapsic 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. Based on a literature review a significant number of articles have been published on Hexadecanedioic acid.

CAS Number

505-54-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,14-Tetradecanedicarboxylic acid	ChEBI
1,16-Hexadecanedioic acid	ChEBI
Thapsic acid	ChEBI
1,14-Tetradecanedicarboxylate	Generator
1,16-Hexadecanedioate	Generator
Thapsate	Generator
Hexadecanedioate	Generator
Α,ω-tetrαdecαnedicαrboxylαte	HMDB
N-Tetradecane-ω,ω'-dicarboxylate	HMDB
N-Tetradecane-ω,ω'-dicarboxylic acid	HMDB
alpha,Omega-tetradecanedicarboxylic acid	HMDB
N-Tetradecane-omega,omega'-dicarboxylic acid	HMDB
N-Tetradecane-ω,ω’-dicarboxylic acid	HMDB
Α,ω-tetradecanedicarboxylic acid	HMDB
Hexadecanedioic acid	MeSH
1, 14-Tetradecanedicarboxylic acid	biospider
A,w-tetradecanedicarboxylate	biospider
A,w-tetradecanedicarboxylic acid	biospider
Hexadecane-1, 16-dioic acid	biospider
Hexadecane-1,16-dioic acid	biospider
Hexadecanedioic	biospider
N-tetradecane-.omega.,.omega.'-dicarboxylic acid	biospider
N-tetradecane-omega,omega'-dicarboxylic acid	biospider
N-tetradecane-w,w'-dicarboxylate	biospider
N-tetradecane-w,w'-dicarboxylic acid	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	4.68	ALOGPS
logP	4.94	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	35.37 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

Chemical Formula

C16H30O4

IUPAC name

hexadecanedioic acid

InChI Identifier

InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)

InChI Key

QQHJDPROMQRDLA-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

286.407

Monoisotopic Molecular Weight

286.214409448

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
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:73722 )
Dicarboxylic acids (LMFA01170022 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 67.10%; H 10.56%; O 22.34%	DFC
Melting Point	Mp 126°	DFC
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01ow-9210000000-ae9c39d4b07c3e8cb742	2015-03-01	View Spectrum
Predicted GC-MS	Hexadecanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-07do-2940000000-8c28631b1022d3318936	Spectrum
Predicted GC-MS	Hexadecanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0109-7691100000-587f0a395c2991f76096	Spectrum
Predicted GC-MS	Hexadecanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hexadecanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hexadecanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hexadecanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0090000000-2311edb5a21bc7c11854	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-01b9-0090000000-29b1e4612ce1b89fe132	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-9000000000-cb4b2bb791cf66c26ad1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 20V, positive	splash10-014r-0490000000-dacc672eeb75f850682b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-014i-0090000000-9e4148fba4082bf62e1e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-014i-2590000000-8bc2ce9bfb76d9bb26b7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-066s-4950000000-47159163bf80115de8b2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-053b-6920000000-8a0094cbb6f9d1650566	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0012-8910000000-2a109bc90ccab90ea68b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-00l2-9700000000-d514011d0869df067d52	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-05o1-9500000000-983b1d8b6bb3f3f63b35	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-015a-9300000000-69f141c415f5b32f3403	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-067j-9200000000-7b8fa454eb425f3e106e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-067i-9100000000-a8b8484850ff331b59c4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-067i-9000000000-2d72212014cb905b53ba	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-066r-9000000000-5f4d3971357b080285ef	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-0aor-9000000000-1f5e11f8710cbd1da2c2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, positive	splash10-0ar0-9100000000-203172aa59c73e588123	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, positive	splash10-0ar0-9200000000-2f3b6e1eff5a4c95e99b	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-21fd3982c0181bc06670	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014u-0390000000-67df6952912c86a0cd98	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-5900000000-ff60e3a81da2e330db67	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-6c700a9c0357a7d235a8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0090000000-fb79a4abfe50390ddb88	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9140000000-7aba6aa5bd7692dcc532	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum