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111-16-0

111-16-0 | Pimelic acid

CAS No: 111-16-0 Catalog No: AG003TSD MDL No:MFCD00004425

Product Description

Catalog Number:
AG003TSD
Chemical Name:
Pimelic acid
CAS Number:
111-16-0
Molecular Formula:
C7H12O4
Molecular Weight:
160.1678
MDL Number:
MFCD00004425
IUPAC Name:
heptanedioic acid
InChI:
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
SMILES:
OC(=O)CCCCCC(=O)O
EC Number:
203-840-8
UNII:
BZQ96WX25F
NSC Number:
30112

Properties

Complexity:
125  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
160.074g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
160.169g/mol
Monoisotopic Mass:
160.074g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.5  

Literature

Title Journal
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Lipid profiling of the Arabidopsis hypersensitive response reveals specific lipid peroxidation and fragmentation processes: biogenesis of pimelic and azelaic acid. Plant physiology 20120901
Development of controlled release formulations of imidacloprid employing novel nano-ranged amphiphilic polymers. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20120101
Metabolomics-based study of clinical and animal plasma samples in coronary heart disease with blood stasis syndrome. Evidence-based complementary and alternative medicine : eCAM 20120101
Tandem synthesis of alternating polyesters from renewable resources. Nature communications 20111213
Contributions of the peroxisome and β-oxidation cycle to biotin synthesis in fungi. The Journal of biological chemistry 20111209
Differential interaction of dicarboxylates with human sodium-dicarboxylate cotransporter 3 and organic anion transporters 1 and 3. American journal of physiology. Renal physiology 20111101
UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. Journal of proteome research 20110902
Two dimensional self-assembly of bis-acylureas having various functional end groups. Journal of colloid and interface science 20110715
Pimelic acid-urea (1/2). Acta crystallographica. Section E, Structure reports online 20110701
Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. Current opinion in chemical biology 20110601
Closing in on complete pathways of biotin biosynthesis. Molecular bioSystems 20110601
Poly[hexa-aqua-bis-(μ(3)-hepta-nedioato-κO:O':O'')dimagnesium]. Acta crystallographica. Section E, Structure reports online 20110601
Functional characterization of a gene cluster involved in gentisate catabolism in Rhodococcus sp. strain NCIMB 12038. Applied microbiology and biotechnology 20110401
Metabolite cross-feeding enhances virulence in a model polymicrobial infection. PLoS pathogens 20110301
Bacterial syntenies: an exact approach with gene quorum. BMC bioinformatics 20110101
Importance of the long-chain fatty acid beta-hydroxylating cytochrome P450 enzyme YbdT for lipopeptide biosynthesis in Bacillus subtilis strain OKB105. International journal of molecular sciences 20110101
Environment sensing and response mediated by ABC transporters. BMC genomics 20110101
In vivo and in silico determination of essential genes of Campylobacter jejuni. BMC genomics 20110101
Metabolomics of oxidative stress in recent studies of endogenous and exogenously administered intermediate metabolites. International journal of molecular sciences 20110101
Evaluating the effects of crystallinity in new biocompatible polyester nanocarriers on drug release behavior. International journal of nanomedicine 20110101
Degradation of a model naphthenic acid, cyclohexanoic acid, by vacuum UV (172 nm) and UV (254 nm)/H2O2. The journal of physical chemistry. A 20101118
Biotin synthesis begins by hijacking the fatty acid synthetic pathway. Nature chemical biology 20100901
Identification of noninvasive biomarkers for alcohol-induced liver disease using urinary metabolomics and the Ppara-null mouse. Journal of proteome research 20100806
Anticancer effects of the MHY218 novel hydroxamic acid-derived histone deacetylase inhibitor in human ovarian cancer cells. International journal of oncology 20100801
Selectivity in a barren landscape: the P450(BioI)-ACP complex. Biochemical Society transactions 20100801
Aerosol volatility and enthalpy of sublimation of carboxylic acids. The journal of physical chemistry. A 20100408
Two new pimelic diphenylamide HDAC inhibitors induce sustained frataxin upregulation in cells from Friedreich's ataxia patients and in a mouse model. PloS one 20100101
Analysis of gene evolution and metabolic pathways using the Candida Gene Order Browser. BMC genomics 20100101
The complete genome sequence of Cupriavidus metallidurans strain CH34, a master survivalist in harsh and anthropogenic environments. PloS one 20100101
A genomic perspective on the potential of Actinobacillus succinogenes for industrial succinate production. BMC genomics 20100101
Chemical probes identify a role for histone deacetylase 3 in Friedreich's ataxia gene silencing. Chemistry & biology 20090925
Radiation metabolomics. 3. Biomarker discovery in the urine of gamma-irradiated rats using a simplified metabolomics protocol of gas chromatography-mass spectrometry combined with random forests machine learning algorithm. Radiation research 20090801
Metabonomics approach to understanding acute and chronic stress in rat models. Journal of proteome research 20090501
Involvement of an alternatively spliced mitochondrial oxodicarboxylate carrier in adipogenesis in 3T3-L1 cells. Journal of biomedical science 20090101
Synthesis, Binding and Fluorescence Studies of Bis-2-amidopyrrole Receptors for Bis-carboxylate Anions. Sensors (Basel, Switzerland) 20090101
Pimelic diphenylamide 106 is a slow, tight-binding inhibitor of class I histone deacetylases. The Journal of biological chemistry 20081219
Structure of bacterial glutathione-S-transferase maleyl pyruvate isomerase and implications for mechanism of isomerisation. Journal of molecular biology 20081205
Use of benzoate as an electron acceptor by Syntrophus aciditrophicus grown in pure culture with crotonate. Environmental microbiology 20081201
Spontaneous reaction silencing in metabolic optimization. PLoS computational biology 20081201
Synthesis and solution structure of 3,5-dioxopimelic acid diesters--stable 1,3,5,7-tetracarbonyl derivatives. Organic & biomolecular chemistry 20080907
(Heptanedioato-κO,O')bis-(1,10-phenanthroline-κN,N')zinc(II) hexa-hydrate. Acta crystallographica. Section E, Structure reports online 20080401
Conformationally constrained diketopimelic acid analogues as inhibitors of dihydrodipicolinate synthase. Bioorganic & medicinal chemistry letters 20080115
Crystal structures and site-directed mutagenesis of a mycothiol-dependent enzyme reveal a novel folding and molecular basis for mycothiol-mediated maleylpyruvate isomerization. The Journal of biological chemistry 20070601
Molecular model for host–guest interaction of tetraamino-tert-butylthiacalix[4]arene and tetraamino-tert-butylcalix[4]arene receptors with carboxylate and dicarboxylate guests: an ONIOM study. Journal of molecular modeling 20070101
Complete gene expression profiling of Saccharopolyspora erythraea using GeneChip DNA microarrays. Microbial cell factories 20070101
A dinuclear lanthanide complex for the recognition of bis(carboxylates): formation of terbium(III) luminescent self-assembly ternary complexes in aqueous solution. Inorganic chemistry 20061113
Histone deacetylase inhibitors reverse gene silencing in Friedreich's ataxia. Nature chemical biology 20061001
Biological significance and development of practical synthesis of biotin. Medicinal research reviews 20060701
The gene ncgl2918 encodes a novel maleylpyruvate isomerase that needs mycothiol as cofactor and links mycothiol biosynthesis and gentisate assimilation in Corynebacterium glutamicum. The Journal of biological chemistry 20060421
Integration of metabolome data with metabolic networks reveals reporter reactions. Molecular systems biology 20060101
Synthesis, Superoxide Dismutase Mimetic and Anticancer Activities of Metal Complexes of 2,2-Dimethylpentanedioic Acid(2dmepdaH(2)) and 3,3-Dimethylpentanedioic acid(3dmepdaH(2)): X-Ray Crystal Structures of [Cu(3dmepda)(bipy)](2). 6H(2)O and [Cu(2dmepda)(bipy)(EtOH)](2). 4EtOH (bipy = 2,2'Bipyridine). Bioinorganic chemistry and applications 20060101
Chemically synthesized pathogen-associated molecular patterns increase the expression of peptidoglycan recognition proteins via toll-like receptors, NOD1 and NOD2 in human oral epithelial cells. Cellular microbiology 20050501
The pimFABCDE operon from Rhodopseudomonas palustris mediates dicarboxylic acid degradation and participates in anaerobic benzoate degradation. Microbiology (Reading, England) 20050301
Spin-labelled vacuolar-ATPase inhibitors in lipid membranes. Biochimica et biophysica acta 20041011
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Viscosity B-coefficients and activation parameters for viscous flow of a solution of heptanedioic acid in aqueous sucrose solution. Carbohydrate research 20031121
X-ray studies on crystalline complexes involving amino acids and peptides. XLI. Commonalities in aggregation and conformation revealed by the crystal structures of the pimelic acid complexes of L-arginine and DL-lysine. Acta crystallographica. Section B, Structural science 20031001
Structural phases of hexamethylenetetramine-pimelic acid (1/1): a unified description based on a stacking model. Acta crystallographica. Section B, Structural science 20030801
Alicycliphilus denitrificans gen. nov., sp. nov., a cyclohexanol-degrading, nitrate-reducing beta-proteobacterium. International journal of systematic and evolutionary microbiology 20030101
Acyl group specificity at the active site of tetrahydridipicolinate N-succinyltransferase. Protein science : a publication of the Protein Society 20020401
Characterization of the initial steps in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase. Biochemistry 20020129
Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates. Journal of the American Chemical Society 20011107
Infrared spectra of the hydrogen bond in pimelic acid crystals: polarization and temperature effects. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20011001
Isotope-tagged cross-linking reagents. A new tool in mass spectrometric protein interaction analysis. Analytical chemistry 20010501
Identification of the human mitochondrial oxodicarboxylate carrier. Bacterial expression, reconstitution, functional characterization, tissue distribution, and chromosomal location. The Journal of biological chemistry 20010316
nag genes of Ralstonia (formerly Pseudomonas) sp. strain U2 encoding enzymes for gentisate catabolism. Journal of bacteriology 20010101
Biochemical and genetic characterization of a gentisate 1, 2-dioxygenase from Sphingomonas sp. strain RW5. Journal of bacteriology 19980801
Anaerobic degradation of pimelate by newly isolated denitrifying bacteria. Microbiology (Reading, England) 19940201
Bacterial metabolism of 5-aminosalicylic acid: enzymic conversion to L-malate, pyruvate and ammonia. Journal of general microbiology 19930501
Inhibition of HIV-1 proteinase by non-peptide carboxylates. Biochemical and biophysical research communications 19910415
Streptomyces DD-carboxypeptidases as transpeptidases. The specificity for amino compounds acting as carboxyl acceptors. The Biochemical journal 19730401
Isolation and characterization of uridine diphosphate-N-glycolylmuramyl-L-alanyl-gamma-D-glutamyl-meso-alpha,alpha'-diaminopimelic acid from Mycobacterium tuberculosis. Biochemical and biophysical research communications 19700408

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