Showing Compound Pimelic acid (FDB022283)

Record Information

Version

1.0

Creation date

2011-09-21 00:11:30 UTC

Update date

2018-05-29 01:52:47 UTC

Primary ID

FDB022283

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pimelic acid

Description

A group of compounds that are derivatives of heptanedioic acid with the general formula R-C7H11O4. Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.[1] In the former route, the additional carbon is suppled by dimethyloxalate, which reacts with the enolate. [HMDB]

CAS Number

111-16-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,5-Pentanedicarboxylic acid	ChEBI
6-Carboxyhexanoic acid	ChEBI
Heptanedioic acid	ChEBI
Pimelate	ChEBI
6-Carboxyhexanoate	Kegg
1,5-Pentanedicarboxylate	Generator
Heptanedioate	Generator
Acid, pimelic	HMDB
Acids, pimelic	HMDB
Pimelic acids	HMDB
1,7-Heptanedioate	HMDB
1,7-Heptanedioic acid	HMDB
Heptandioate	HMDB
Heptandioic acid	HMDB
Heptane-1,7-dioate	HMDB
Heptane-1,7-dioic acid	HMDB
Pilerate	HMDB
Pileric acid	HMDB
6-carboxyhexanoate	hmdb
6-carboxyhexanoic acid	hmdb
Pimelic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	13.3 g/L	ALOGPS
logP	0.51	ALOGPS
logP	0.94	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.05	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	6	ChemAxon
Refractivity	37.34 m³·mol⁻¹	ChemAxon
Polarizability	16.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H12O4

IUPAC name

heptanedioic acid

InChI Identifier

InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)

InChI Key

WLJVNTCWHIRURA-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCCC(O)=O

Average Molecular Weight

160.1678

Monoisotopic Molecular Weight

160.073558872

Classification

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-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:30531 )
Dicarboxylic acids (C02656 )
Dicarboxylic acids (LMFA01170051 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

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
GC-MS	Pimelic acid, non-derivatized, GC-MS Spectrum	splash10-056s-1910000000-58bf29a41b2e4b405df9	Spectrum
GC-MS	Pimelic acid, non-derivatized, GC-MS Spectrum	splash10-0r7l-9100000000-aeff5d9828ac92b33028	Spectrum
GC-MS	Pimelic acid, non-derivatized, GC-MS Spectrum	splash10-054k-1910000000-fc6cb63b081b4f5f7fd3	Spectrum
GC-MS	Pimelic acid, non-derivatized, GC-MS Spectrum	splash10-056s-1910000000-58bf29a41b2e4b405df9	Spectrum
GC-MS	Pimelic acid, non-derivatized, GC-MS Spectrum	splash10-054k-1900000000-403538c5b4091abf0a3d	Spectrum
Predicted GC-MS	Pimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-3bc5f898da696375482f	Spectrum
Predicted GC-MS	Pimelic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00y0-9720000000-f599c8c7e2d374dc1d0c	Spectrum
Predicted GC-MS	Pimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pimelic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pimelic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pimelic 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)	splash10-0002-9300000000-a3d2b3924fcede41e331	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0002-9100000000-7050dc1518d598ad5051	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052e-9200000000-84550d0cfeb05e8d79bd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0r7l-9100000000-b698134a5d1e523a961e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0900000000-a3b877a40a98e4d07993	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-9500000000-6f90176eaadac29eae28	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9000000000-859f1028218d04c20dc6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9000000000-ef436118494b323530f4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-15fa4059d8c10e1e3a03	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-a3b877a40a98e4d07993	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9500000000-6f90176eaadac29eae28	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-0ece97699a3ecbbd29c5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-aa9d7a3b0b034eb999ac	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-15fa4059d8c10e1e3a03	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-bbaaf04acf7504d9af12	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2467588398a0cc1a7173	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-9000000000-2c0303cc46347643edee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9200000000-62e7353cf7ec99f7b257	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9700000000-51105e097da7cfc85c56	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1900000000-f72d396c48eae140d2ea	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-6900000000-148d1369a6cc8216a4d4	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-8148e8a28ecc0a5f1819	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-97c3b22812cb1495f92e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-ec8e65ccb8032a2fffa0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-c8c106238d3a22f75dbc	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum