pimelic acid (CHEBI:30531)

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CHEBI:30531 - pimelic acid

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ChEBI Name	pimelic acid

ChEBI ID	CHEBI:30531

Definition	An α,ω-dicarboxylic acid that is pentane with two carboxylic acid groups at positions C-1 and C-5.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:20709, CHEBI:44980, CHEBI:24517

Supplier Information	ChemicalBook:CB3329360, eMolecules:530979, ZINC000001529489

Download	Molfile XML SDF

more structures >>

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23 22 0 0 0 0 999 V2000

-3.3845 -2.8749 -1.7352 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2741 -2.8457 -1.2244 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9406 -1.8839 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7781 -0.9469 -0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3952 0.0758 0.4878 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7750 0.9949 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1779 2.0204 1.1528 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2734 2.8669 0.7335 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1424 4.0777 0.6343 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4493 -3.6618 -1.6206 O 0 0 0 0 0 0 0 0 0 0 0 0

3.3628 2.3768 0.4559 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.6655 -2.4312 0.7098 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8130 -1.2712 0.0526 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1066 -1.5479 -0.8398 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0597 -0.4061 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1119 -0.4638 1.3962 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2672 0.6923 0.7220 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4917 1.5326 -0.8467 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6380 0.3659 -0.1764 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3016 2.6269 1.4040 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4745 1.4927 2.0637 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6332 -3.6677 -1.2877 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0285 2.8783 0.1757 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 2 0 0 0 0

3 2 1 0 0 0 0

4 3 1 0 0 0 0

5 4 1 0 0 0 0

6 5 1 0 0 0 0

7 6 1 0 0 0 0

8 7 1 0 0 0 0

9 8 2 0 0 0 0

10 2 1 0 0 0 0

11 8 1 0 0 0 0

3 12 1 0 0 0 0

3 13 1 0 0 0 0

4 14 1 0 0 0 0

4 15 1 0 0 0 0

5 16 1 0 0 0 0

5 17 1 0 0 0 0

6 18 1 0 0 0 0

6 19 1 0 0 0 0

7 20 1 0 0 0 0

7 21 1 0 0 0 0

10 22 1 0 0 0 0

11 23 1 0 0 0 0

M END): 33 ms

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Wikipedia	License
Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Pimelic acid is one CH2 unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid lysine and the vitamin biotin.
Read full article at Wikipedia

Formula

C7H12O4

Net Charge

Average Mass

160.16778

Monoisotopic Mass

160.07356

InChI

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

InChIKey

WLJVNTCWHIRURA-UHFFFAOYSA-N

SMILES

OC(=O)CCCCCC(O)=O

Metabolite of Species	Details
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	pimelic acid (CHEBI:30531) has role Daphnia magna metabolite (CHEBI:83056) pimelic acid (CHEBI:30531) has role Escherichia coli metabolite (CHEBI:76971) pimelic acid (CHEBI:30531) is a α,ω-dicarboxylic acid (CHEBI:28383) pimelic acid (CHEBI:30531) is a dicarboxylic fatty acid (CHEBI:189840) pimelic acid (CHEBI:30531) is conjugate acid of pimelate (CHEBI:133773) pimelic acid (CHEBI:30531) is conjugate acid of pimelate(1−) (CHEBI:17774)

Incoming	(S)-2-amino-6-oxopimelic acid (CHEBI:28245) has functional parent pimelic acid (CHEBI:30531) 2,6-diaminopimelic acid (CHEBI:23673) has functional parent pimelic acid (CHEBI:30531) 2-oxopimelic acid (CHEBI:72700) has functional parent pimelic acid (CHEBI:30531) 3-oxopimelic acid (CHEBI:37259) has functional parent pimelic acid (CHEBI:30531) 4-hydroxy-2-oxoheptanedioic acid (CHEBI:73089) has functional parent pimelic acid (CHEBI:30531) O-pimelylcarnitine (CHEBI:86084) has functional parent pimelic acid (CHEBI:30531) L-2-succinylamino-6-oxoheptanedioic acid (CHEBI:35266) has functional parent pimelic acid (CHEBI:30531) pimeloyl-CoA (CHEBI:15504) has functional parent pimelic acid (CHEBI:30531) pimelate (CHEBI:133773) is conjugate base of pimelic acid (CHEBI:30531) pimelate(1−) (CHEBI:17774) is conjugate base of pimelic acid (CHEBI:30531)

IUPAC Name

heptanedioic acid

Synonyms	Sources
1,5-pentanedicarboxylic acid	ChemIDplus
6-carboxyhexanoic acid	ChEBI
Heptanedioic acid	KEGG COMPOUND
Pimelate	KEGG COMPOUND
PIMELIC ACID	PDBeChem
Pimelic acid	KEGG COMPOUND

Manual Xrefs	Databases
C00001199	KNApSAcK
C02656	KEGG COMPOUND
CPD-205	MetaCyc
DB01856	DrugBank
HMDB0000857	HMDB
LMFA01170051	LIPID MAPS
Pimelic_acid	Wikipedia
PML	PDBeChem
View more database links

Registry Numbers	Types	Sources
111-16-0	CAS Registry Number	KEGG COMPOUND
111-16-0	CAS Registry Number	ChemIDplus
1210024	Reaxys Registry Number	Reaxys
261058	Gmelin Registry Number	Gmelin

Citations

Peters-Wendisch P, Götker S, Heider SA, Komati Reddy G, Nguyen AQ, Stansen KC, Wendisch VF (2014)
Engineering biotin prototrophic Corynebacterium glutamicum strains for amino acid, diamine and carotenoid production.
Journal of biotechnology 192 Pt B, 346-354 [PubMed:24486440]
[show Abstract]

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Lin S, Cronan JE (2011)
Closing in on complete pathways of biotin biosynthesis.
Molecular bioSystems 7, 1811-1821 [PubMed:21437340]
[show Abstract]

Lin S, Hanson RE, Cronan JE (2010)
Biotin synthesis begins by hijacking the fatty acid synthetic pathway.
Nature chemical biology 6, 682-688 [PubMed:20693992]
[show Abstract]

Last Modified

23 February 2022

CHEBI:30531 - pimelic acid

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