Identification

Name
Glutaric Acid
Accession Number
DB03553  (EXPT01668)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
H849F7N00B
CAS number
110-94-1
Weight
Average: 132.1146
Monoisotopic: 132.042258744
Chemical Formula
C5H8O4
InChI Key
JFCQEDHGNNZCLN-UHFFFAOYSA-N
InChI
InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)
IUPAC Name
pentanedioic acid
SMILES
OC(=O)CCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAspartate aminotransferaseNot AvailableEscherichia coli (strain K12)
UGlutamate decarboxylase alphaNot AvailableEscherichia coli (strain K12)
UBranched-chain-amino-acid aminotransferaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
L-Glutamate MetabolismMetabolic
Lysine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetazolamideThe excretion of Glutaric Acid can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe excretion of Glutaric Acid can be decreased when combined with Acetylsalicylic acid.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Glutaric Acid.
Adefovir DipivoxilThe excretion of Adefovir Dipivoxil can be decreased when combined with Glutaric Acid.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Glutaric Acid.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Glutaric Acid.
AmoxicillinThe excretion of Glutaric Acid can be decreased when combined with Amoxicillin.
BaclofenThe excretion of Glutaric Acid can be decreased when combined with Baclofen.
BenzylpenicillinThe excretion of Glutaric Acid can be decreased when combined with Benzylpenicillin.
BumetanideThe excretion of Bumetanide can be decreased when combined with Glutaric Acid.
Food Interactions
Not Available

References

Synthesis Reference

Guiseppe Gigliotti, Jean-Michel Roul, "Process for the preparation of 3-methyl-3-hydroxy-glutaric acid." U.S. Patent US4467108, issued June, 1980.

US4467108
General References
Not Available
External Links
Human Metabolome Database
HMDB0000661
KEGG Compound
C00489
PubChem Compound
743
PubChem Substance
46506371
ChemSpider
723
ChEBI
17859
ChEMBL
CHEMBL1162495
HET
GUA
Wikipedia
Glutaric_acid
PDB Entries
1ams / 1b4n / 1czc / 1iyd / 1jw0 / 1xey / 3p4r / 4jxy / 4lh3 / 4utr
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)97.8 °CPhysProp
boiling point (°C)303 °CPhysProp
water solubility1.6E+006 mg/L (at 28 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.29HANSCH,C ET AL. (1995)
logS1ADME Research, USCD
pKa4.34 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility56.0 mg/mLALOGPS
logP-0.25ALOGPS
logP0.046ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.14 m3·mol-1ChemAxon
Polarizability12.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5167
Blood Brain Barrier+0.8713
Caco-2 permeable-0.6629
P-glycoprotein substrateNon-substrate0.734
P-glycoprotein inhibitor INon-inhibitor0.9848
P-glycoprotein inhibitor IINon-inhibitor0.9653
Renal organic cation transporterNon-inhibitor0.9436
CYP450 2C9 substrateNon-substrate0.8292
CYP450 2D6 substrateNon-substrate0.9096
CYP450 3A4 substrateNon-substrate0.7522
CYP450 1A2 substrateNon-inhibitor0.8704
CYP450 2C9 inhibitorNon-inhibitor0.9683
CYP450 2D6 inhibitorNon-inhibitor0.9709
CYP450 2C19 inhibitorNon-inhibitor0.9812
CYP450 3A4 inhibitorNon-inhibitor0.966
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9931
Ames testNon AMES toxic0.9462
CarcinogenicityNon-carcinogens0.8197
BiodegradationReady biodegradable0.9123
Rat acute toxicity1.5523 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9651
hERG inhibition (predictor II)Non-inhibitor0.9751
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0f6t-2940000000-9f099473c4a6eb94d4be
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-1920000000-4ade63738a1c00460a63
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-1910000000-743df9571fee7baa3417
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00fs-9710000000-ba958e52b1424e5d4840
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0cgj-3930000000-298fe512c6b58220ee33
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-052o-9000000000-663deab1ce6413c4859d
GC-MS Spectrum - EI-BGC-MSsplash10-0002-0920000000-56bce366cac24cd6773f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6t-2940000000-9f099473c4a6eb94d4be
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1920000000-4ade63738a1c00460a63
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1910000000-743df9571fee7baa3417
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00fs-9710000000-ba958e52b1424e5d4840
GC-MS Spectrum - GC-MSGC-MSsplash10-0cgj-3930000000-298fe512c6b58220ee33
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0910000000-86fbcf8f1c72fbb2ffd0
Mass Spectrum (Electron Ionization)MSsplash10-052o-9000000000-f308daa4e82c16019e0d
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-0019-9500000000-9db56ca3a541f0ce07d1
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-052r-9100000000-991f69d0892976558f85
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-0536-9300000000-20fb2c8dd136e4924aca
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-052o-9000000000-663deab1ce6413c4859d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-8eb90c15915f014713ac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-9200000000-2ffdc08c49952e135a86
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-000i-9000000000-8884b857c9582288f35a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-052f-9000000000-7d2c0333bdce4dbabbc6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-9ab2a948083302641628
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-000i-9400000000-c5ec3115706f6041b868
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-8eb90c15915f014713ac
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9200000000-2ffdc08c49952e135a86
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-8884b857c9582288f35a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-052f-9000000000-7d2c0333bdce4dbabbc6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-9ab2a948083302641628
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-9400000000-c5ec3115706f6041b868
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Fatty acids and conjugates / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Fatty acid / Dicarboxylic acid or derivatives / Carboxylic acid / 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:17859) / Dicarboxylic acids (C00489)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Not Available
Gene Name
aspC
Uniprot ID
P00509
Uniprot Name
Aspartate aminotransferase
Molecular Weight
43572.965 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extr...
Gene Name
gadA
Uniprot ID
P69908
Uniprot Name
Glutamate decarboxylase alpha
Molecular Weight
52684.685 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
L-valine transaminase activity
Specific Function
Acts on leucine, isoleucine and valine.
Gene Name
ilvE
Uniprot ID
P0AB80
Uniprot Name
Branched-chain-amino-acid aminotransferase
Molecular Weight
34093.4 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807]
  2. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [PubMed:9950961]
  3. Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. [PubMed:9827570]
  4. Aslamkhan A, Han YH, Walden R, Sweet DH, Pritchard JB: Stoichiometry of organic anion/dicarboxylate exchange in membrane vesicles from rat renal cortex and hOAT1-expressing cells. Am J Physiol Renal Physiol. 2003 Oct;285(4):F775-83. Epub 2003 Jul 1. [PubMed:12837685]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
  2. Bakhiya A, Bahn A, Burckhardt G, Wolff N: Human organic anion transporter 3 (hOAT3) can operate as an exchanger and mediate secretory urate flux. Cell Physiol Biochem. 2003;13(5):249-56. [PubMed:14586168]
  3. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [PubMed:14762099]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [PubMed:10660625]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:37