Identification

Name
Pidolic Acid
Accession Number
DB03088  (EXPT00247)
Type
Small Molecule
Groups
Approved, Investigational
Description

Pidolic acid is a naturally occurring but little-studied amino acid derivative that can be formed enzymatically or non-enzymatically and participates as a biological intermediate with unique pharmacodynamics in various chemical pathways [4, 7]. Elevations of the acid in blood levels may be associated with problems of glutamine or glutathione metabolism [7]. Pidolic acid, in general, is found in large quantities in brain tissue and other tissues in bound form, like skin [7].

There are currently little to no medicines available that are clinically approved or marketed for employing pidolic acid as an active ingredient for any particular formal indication. Although pidolic acid is included in some over-the-counter, non-prescription dietary supplements for the proposed purpose of facilitating cognitive or memory enhancement, most available research suggest exercising caution in their recommendation as much more research is necessary [1, 2].

Structure
Thumb
Synonyms
  • (−)-2-pyrrolidone-5-carboxylic acid
  • (S)-(−)-2-pyrrolidone-5-carboxylic acid
  • (S)-pyroglutamic acid
  • 5-L-oxoproline
  • 5-oxo-2-pyrrolidinecarboxylic acid
  • 5-oxo-L-proline
  • 5-Pyrrolidone-2-carboxylic acid
  • Glutimic acid
  • L-5-Pyrrolidone-2-carboxylic acid
  • L-pyroglutamic acid
  • L-pyrrolidone carboxylic acid
  • PCA
  • Pidolic Acid
  • Pyroglutamic Acid
Product Ingredients
IngredientUNIICASInChI Key
Magnesium pidolateV5PC588N7G62003-27-4JQAACYUZYRBHGG-QHTZZOMLSA-L
Zinc pidolateC32PQ86DH415454-75-8OWVLYQRCCIEOPF-QHTZZOMLSA-L
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mag 2 Pwr 1.5gm/pckPowder1.5 gOralLaboratoires Charton Laboratories1990-12-311999-01-16Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Cleansing Foaming Gel Acne Pro SkinZinc pidolate (.072 mg/120mg) + Orris (1.8 mg/120mg) + Salicylic acid (12 mg/120mg)GelTopicalLange SAS2012-07-18Not applicableUs
Categories
UNII
SZB83O1W42
CAS number
98-79-3
Weight
Average: 129.114
Monoisotopic: 129.042593095
Chemical Formula
C5H7NO3
InChI Key
ODHCTXKNWHHXJC-VKHMYHEASA-N
InChI
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
IUPAC Name
(2S)-5-oxopyrrolidine-2-carboxylic acid
SMILES
OC(=O)[C@@H]1CCC(=O)N1

Pharmacology

Indication

There is currently no clinically approved and/or marketed medicine that relies upon pidolic acid as an active ingredient for any formal therapeutic indication.

Although pidolic acid may be sold in a variety of non-prescription, over-the-counter dietary supplement products for cognitive or memory enhancement, there are many studies that suggest that such products or such supplementation do not elicit any kind of cognitive benefit to users [1, 2]. In fact, the general suggestion for any such pidolic acid product is to exercise caution in their recommendation as much more research is necessary [1].

Pidolic acid and sodium pidolic acid are, however, used to some extent in skin and hair conditioning agents owing to their humectant characteristics [9].

Associated Conditions
Pharmacodynamics

Pidolic acid is a naturally occurring but little-studied amino acid derivative that can be formed enzymatically or non-enzymatically and participates as a biological intermediate in various chemical pathways [4, 7]. Elevations of the acid in blood levels may be associated with problems of glutamine or glutathione metabolism [7]. Pidolic acid, in general, is found in large quantities in brain tissue and other tissues in bound form, like skin [7].

Moreover, pidolic acid in high enough levels can act as an acidogen capable of inducing acidosis and a metabotoxin that can result in adverse health effects [7]. Chronically elevated levels of pidolic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria (where 5-oxoproline is otherwise known as pidolic acid), 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia [7]. In particular, abnormally high levels of organic acids like pidolic acid in the blood, urine, brain, and/or other tissues results in general metabolic acidosis [7]. Such acidosis generally occurs when arterial pH falls below 7.35 [7]. In infants, the initial symptoms of acidosis consist of poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy [7]. Eventually, acidosis and the symptoms of acidosis can lead to heart, liver, and kidney abnormalities, seizures, coma, and possibly even death [7]. Many children who are afflicted with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures [7].

High levels of pidolic acid in the blood have also been demonstrated following acetaminophen overdose, causing an increased level of acidity called a high anion gap metabolic acidosis [5].

Mechanism of action

Pidolic acid is an endogenous amino acid derivative where the free amino group of glutamic acid or glutamine cyclizes to generate a lactam [4, 7]. Subsequently it is also a metabolite in the glutathione cycle that is converted to glutamate by the enzyme 5-oxoprolinase [4, 7]. Moreover, N-terminal glutamic acid and glutamine residues can either spontaneously cyclize to become pidolic acid, or be enzymatically transformed by glutaminyl cyclases [4, 7]. In particular, this is ultimately a form of N-termini that is a challenge for N-terminal sequencing using Edman chemistry, which necessitates a free primary amino group that is not present in pidolic acid [4, 7]. Pyroglutamate aminopeptidase can restore a free N-terminus by cleaving off the pyroglutamate residue, however [4, 7].

Additionally, pidolic acid and certain pidolic acid salts like calcium, magnesium, and potassium pidolic acid are sometimes used as skin or hair conditioning agents because of their humectant effects [9]. In such humectant formulations, hydrophilic amine, hydroxyl, or even carboxyl groups possess high affinities for forming hydrogen bonds with molecules of water, allowing the hygroscopic formulations to attract and retain moisture in the air nearby through absorption, therefore drawing the water vapor into the formulation.

TargetActionsOrganism
UVascular endothelial growth factor ANot AvailableHuman
UPancreatic alpha-amylaseNot AvailableHuman
UIg lambda-1 chain C regionsNot AvailableHuman
UIg lambda chain V-II region MGCNot AvailableHuman
UTrefoil factor 2Not AvailableHuman
UCytochrome c2Not AvailableRhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
UDisintegrin and metalloproteinase domain-containing protein 28Not AvailableHuman
UEndo-1,4-beta-xylanaseNot AvailableBacillus agaradhaerens
UDissimilatory copper-containing nitrite reductaseNot AvailableAlcaligenes xylosoxydans xylosoxydans
UKeratin-associated protein 5-2Not AvailableHuman
UOrexinNot AvailableHuman
UC-C motif chemokine 8Not AvailableHuman
UCytochrome c'Not AvailableAlcaligenes xylosoxydans xylosoxydans
UAlpha-amylase 2BNot AvailableHuman
UAngiogeninNot AvailableHuman
UChondroitinase-BNot AvailablePedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
UAlpha-amylase 1Not AvailableHuman
Absorption

In skin conditioning agents, it has been observed that the percutaneous absorption of 5, 10, and 20% sodium pidolic acid through human skin was 5.97, 6.78, and 5.89%, respectively [9].

Volume of distribution

Readily available data regarding the volume of distribution of pidolic acid is not available.

Protein binding

Readily available data regarding the protein binding of pidolic acid is not available.

Metabolism

In living cells, various metabolic pathways involving pidolic acid exist: (a) glutamyl/glutaminyl (amino acid) n is converted to pyroglutamyl- (amino acid) n by glutaminyl cyclase, pyroglutamyl- (amino acid) n is then metabolised to pyroglutamic acid (pidolic acid) by pyroglutamyl peptidase; (b) via the gamma-Glutamyl cycle, gamma-Glutamyl transpeptidase generates gamma-Glutamyl amino acid which is metabolised to pyroglutamic acid via gamma-Glutamyl cyclotransferase; (c) glutamate via gamma-Glutamylcysteine synthetase or Glutamine synthetase or Glutamate 5-kinase metabolism generates gamma-Glutamyl phosphate which itself can be converted to pyroglutamic acid; and (d) glutamate or glutamine can be non-enzymatically converted to pyroglutamic acid [8]. Finally, pyroglutamic acid (or pidolic acid) itself is metabolized to glutamate via the 5-Oxoprolinase enzyme [8].

Route of elimination

In the dog animal model, it was determined that 30% of an absorbed oral administration of pidolic acid was excreted unchanged in the urine and the remainder converted to urea [9].

Half life

Some studies have determined that the specific half-life of the N-terminal glutamic acid is about 9 months in a pH 4.1 buffer at 45 degrees Celsius [6].

Clearance

Readily available data regarding the clearance of pidolic acid is not available.

Toxicity

High levels of pidolic acid in the blood can lead to 5-Oxoprolinuria, which can ultimately result in severe metabolic acidosis, hemolytic anaemia, or even central nervous system dysfunction [8].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Glutathione MetabolismMetabolic
Glutathione Synthetase DeficiencyDisease
gamma-Glutamyltransferase DeficiencyDisease
gamma-Glutamyltranspeptidase DeficiencyDisease
5-OxoprolinuriaDisease
5-Oxoprolinase DeficiencyDisease
Glutathione MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

John G. Black, Ian R. Scott, "Pyroglutamic acid esters, their synthesis and use in topical products." U.S. Patent US4774255, issued December, 1974.

US4774255
General References
  1. McDougall GJ Jr, Austin-Wells V, Zimmerman T: Utility of nutraceutical products marketed for cognitive and memory enhancement. J Holist Nurs. 2005 Dec;23(4):415-33. doi: 10.1177/0898010105280097. [PubMed:16251490]
  2. Dellavecchia MJ: Inaccurate serelaxin chemical structure. P T. 2013 Dec;38(12):763. [PubMed:24391398]
  3. Schilling S, Wasternack C, Demuth HU: Glutaminyl cyclases from animals and plants: a case of functionally convergent protein evolution. Biol Chem. 2008 Aug;389(8):983-91. doi: 10.1515/BC.2008.111. [PubMed:18979624]
  4. Podell DN, Abraham GN: A technique for the removal of pyroglutamic acid from the amino terminus of proteins using calf liver pyroglutamate amino peptidase. Biochem Biophys Res Commun. 1978 Mar 15;81(1):176-85. [PubMed:26343]
  5. Liss DB, Paden MS, Schwarz ES, Mullins ME: What is the clinical significance of 5-oxoproline (pyroglutamic acid) in high anion gap metabolic acidosis following paracetamol (acetaminophen) exposure? Clin Toxicol (Phila). 2013 Nov;51(9):817-27. doi: 10.3109/15563650.2013.844822. Epub 2013 Oct 11. [PubMed:24111553]
  6. Chelius D, Jing K, Lueras A, Rehder DS, Dillon TM, Vizel A, Rajan RS, Li T, Treuheit MJ, Bondarenko PV: Formation of pyroglutamic acid from N-terminal glutamic acid in immunoglobulin gamma antibodies. Anal Chem. 2006 Apr 1;78(7):2370-6. doi: 10.1021/ac051827k. [PubMed:16579622]
  7. HMDB: Pyroglutamic Acid Metabocard [Link]
  8. Pyroglutamic acid: throwing light on a lightly studied metabolite [Link]
  9. Cosmetic Ingredient Review: Safety Assessment of PCA and Its Salts as Used in Cosmetics [File]
External Links
Human Metabolome Database
HMDB0000267
KEGG Compound
C01879
PubChem Compound
7405
PubChem Substance
46506886
ChemSpider
7127
ChEBI
18183
ChEMBL
CHEMBL397976
HET
PCA
ATC Codes
A12CC08 — Magnesium pidolate
PDB Entries
1a39 / 1a8j / 1aqk / 1ayj / 1b1i / 1b2w / 1b2y / 1b30 / 1b31 / 1b3v
show 702 more
MSDS
Download (47.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)1
2TerminatedTreatmentHemoglobin SC Disease2
2, 3CompletedTreatmentIntracranial Surgery1
3CompletedBasic ScienceProstate Cancer1
3CompletedTreatmentPostoperative pain1
3RecruitingTreatmentAortic Aneurysm, Abdominal / Local Anesthesia / Pain NOS1
4CompletedNot AvailableHealthy Volunteers1
4CompletedTreatmentAnalgesia, Patient-Controlled / Pain NOS / Postoperative pain1
4CompletedTreatmentFamily History of Diabetes / Family History of Metabolic Syndrome1
4CompletedTreatmentGeneral Surgery / Pneumonia / Surgical Site Infections1
4CompletedTreatmentPostoperative pain1
Not AvailableCompletedNot AvailableInfection, Postoperative Wound1
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Arthropathy of Knee Joint / Knee Osteoarthritis (Knee OA) / Knee Pain Chronic / Rheumatoid Arthritis1
Not AvailableRecruitingTreatmentLocal Anesthesia / Neoplasm, Bladder / Opioids Use / Pelvic Neoplasms / Postoperative pain / Prostate Neoplasms / Urologic Neoplasms1
Not AvailableUnknown StatusSupportive CarePost Operative Pain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical
PowderOral1.5 g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)184.7 °CPhysProp
water solubility4.76E+005 mg/L (at 13 °C)BEILSTEIN
Predicted Properties
PropertyValueSource
Water Solubility151.0 mg/mLALOGPS
logP-1ALOGPS
logP-0.89ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m3·mol-1ChemAxon
Polarizability11.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.844
Blood Brain Barrier+0.9612
Caco-2 permeable-0.7558
P-glycoprotein substrateNon-substrate0.6844
P-glycoprotein inhibitor INon-inhibitor0.9821
P-glycoprotein inhibitor IINon-inhibitor0.997
Renal organic cation transporterNon-inhibitor0.9233
CYP450 2C9 substrateNon-substrate0.8193
CYP450 2D6 substrateNon-substrate0.8251
CYP450 3A4 substrateNon-substrate0.6317
CYP450 1A2 substrateNon-inhibitor0.9641
CYP450 2C9 inhibitorNon-inhibitor0.9782
CYP450 2D6 inhibitorNon-inhibitor0.9678
CYP450 2C19 inhibitorNon-inhibitor0.9812
CYP450 3A4 inhibitorNon-inhibitor0.9931
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9973
Ames testNon AMES toxic0.9497
CarcinogenicityNon-carcinogens0.9744
BiodegradationReady biodegradable0.9363
Rat acute toxicity2.0801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9923
hERG inhibition (predictor II)Non-inhibitor0.9791
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-MSsplash10-0ab9-8900000000-f79dc90370ba38f587c9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ab9-8900000000-f79dc90370ba38f587c9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-90fb43273551aeb9b2c4
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-001i-9500000000-ebc64308ec5d5bdb303e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-053r-9000000000-7377cb17491942e9589c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-053u-9000000000-fcab1396867356ebd6ae
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-5b0c6536e1b3217b8544
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-c30ac0bd264c8007ef92
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004i-5900000000-ea3a164653e4235716ae
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0f89-9000000000-f6620738e68f990d0594
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0udi-9000000000-7937bee2e9a6d6b29cbd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-f20401903b234914b936
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-9446bb65e0edd72cfd59
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0059-7900000000-74eccdeb9f0d5fd17614
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0f8a-9000000000-8786a9cd5e488192f34d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0f6t-9000000000-ebcc1ac4acd525218e80
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-01q9-2900000000-754ae9b699ec1b22cd76
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-9300000000-eabb8c4dc0d1111e0431
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00lr-9100000000-1dd17702aee7e5bce618
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-067i-9000000000-c9669794d3a8746be498
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-9e103abb0a6ed890051e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03e9-3900000000-da8cf252285c1d616586
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-01q9-9400000000-96a7fe5a81188c49d1ba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-014i-9000000000-356215339a43217dea66
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-02vl-9000000000-ed47ec6e675eb338da19
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-f647da344adbdf7bfb1b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-9200000000-0bddc68d58c6fb981d1a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-004i-0900000000-c70c79fa828bbf137ebc
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/MSsplash10-004i-0900000000-5b0c6536e1b3217b8544
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-c30ac0bd264c8007ef92
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-5900000000-ea3a164653e4235716ae
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0f89-9000000000-f6620738e68f990d0594
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-9000000000-7937bee2e9a6d6b29cbd
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-f20401903b234914b936
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-9446bb65e0edd72cfd59
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0059-7900000000-74eccdeb9f0d5fd17614
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0f8a-9000000000-8786a9cd5e488192f34d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0f6t-9000000000-ebcc1ac4acd525218e80
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-0900000000-c70c79fa828bbf137ebc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-2900000000-754ae9b699ec1b22cd76
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9300000000-eabb8c4dc0d1111e0431
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-9100000000-1dd17702aee7e5bce618
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-067i-9000000000-c9669794d3a8746be498
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-9e103abb0a6ed890051e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03e9-3900000000-da8cf252285c1d616586
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-9400000000-96a7fe5a81188c49d1ba
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-356215339a43217dea66
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-02vl-9000000000-ed47ec6e675eb338da19
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-f647da344adbdf7bfb1b
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-001i-9000000000-0f1d7e67dfe0b5f4f6c3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9200000000-0bddc68d58c6fb981d1a
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Pyrroline carboxylic acids / Cyclic carboximidic acids / Lactims / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Alpha-amino acid or derivatives / Pyrroline carboxylic acid / Pyrroline carboxylic acid or derivatives / Pyrroline / Cyclic carboximidic acid / Lactim / Carboxylic acid / Monocarboxylic acid or derivatives / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound
show 11 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-proline derivative, 5-oxoproline (CHEBI:18183) / Other amino acids (C01879)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vascular endothelial growth factor receptor binding
Specific Function
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
Gene Name
VEGFA
Uniprot ID
P15692
Uniprot Name
Vascular endothelial growth factor A
Molecular Weight
27042.205 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Chloride ion binding
Specific Function
Not Available
Gene Name
AMY2A
Uniprot ID
P04746
Uniprot Name
Pancreatic alpha-amylase
Molecular Weight
57706.51 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Immunoglobulin receptor binding
Specific Function
Not Available
Gene Name
IGLC1
Uniprot ID
P0CG04
Uniprot Name
Ig lambda-1 chain C regions
Molecular Weight
11347.585 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Antigen binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P01709
Uniprot Name
Ig lambda chain V-II region MGC
Molecular Weight
11557.51 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Inhibits gastrointestinal motility and gastric acid secretion. Could function as a structural component of gastric mucus, possibly by stabilizing glycoproteins in the mucus gel through interactions...
Gene Name
TFF2
Uniprot ID
Q03403
Uniprot Name
Trefoil factor 2
Molecular Weight
14284.12 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Rhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Cytochrome c2 is found mainly in purple, non-sulfur, photosynthetic bacteria where it functions as the electron donor to the oxidized bacteriochlorophyll in the photophosphorylation pathway. Howeve...
Gene Name
cycA
Uniprot ID
P00091
Uniprot Name
Cytochrome c2
Molecular Weight
14632.81 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. ...
Gene Name
ADAM28
Uniprot ID
Q9UKQ2
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight
87147.04 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Bacillus agaradhaerens
Pharmacological action
Unknown
General Function
Endo-1,4-beta-xylanase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q7SIE2
Uniprot Name
Endo-1,4-beta-xylanase
Molecular Weight
23307.82 Da
Kind
Protein
Organism
Alcaligenes xylosoxydans xylosoxydans
Pharmacological action
Unknown
General Function
Nitrite reductase (no-forming) activity
Specific Function
Not Available
Gene Name
nir
Uniprot ID
O68601
Uniprot Name
Copper-containing nitrite reductase
Molecular Weight
38939.295 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
In the hair cortex, hair keratin intermediate filaments are embedded in an interfilamentous matrix, consisting of hair keratin-associated protein (KRTAP), which are essential for the formation of a...
Gene Name
KRTAP5-2
Uniprot ID
Q701N4
Uniprot Name
Keratin-associated protein 5-2
Molecular Weight
16270.68 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Neuropeptides that play a significant role in the regulation of food intake and sleep-wakefulness, possibly by coordinating the complex behavioral and physiologic responses of these complementary h...
Gene Name
HCRT
Uniprot ID
O43612
Uniprot Name
Orexin
Molecular Weight
13362.51 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase activity
Specific Function
Chemotactic factor that attracts monocytes, lymphocytes, basophils and eosinophils. May play a role in neoplasia and inflammatory host responses. This protein can bind heparin. The processed form M...
Gene Name
CCL8
Uniprot ID
P80075
Uniprot Name
C-C motif chemokine 8
Molecular Weight
11246.24 Da
Kind
Protein
Organism
Alcaligenes xylosoxydans xylosoxydans
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Cytochrome c' is the most widely occurring bacterial c-type cytochrome. Cytochromes c' are high-spin proteins and the heme has no sixth ligand. Their exact function is not known.
Gene Name
Not Available
Uniprot ID
P00138
Uniprot Name
Cytochrome c'
Molecular Weight
13628.35 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Alpha-amylase activity
Gene Name
AMY2B
Uniprot ID
P19961
Uniprot Name
Alpha-amylase 2B
Molecular Weight
57709.49 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rrna binding
Specific Function
Binds to actin on the surface of endothelial cells; once bound, angiogenin is endocytosed and translocated to the nucleus. Stimulates ribosomal RNA synthesis including that containing the initiatio...
Gene Name
ANG
Uniprot ID
P03950
Uniprot Name
Angiogenin
Molecular Weight
16549.95 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
Pedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
Pharmacological action
Unknown
General Function
Chondroitin b lyase activity
Specific Function
Cleaves the glycosaminoglycan, dermatan sulfate.
Gene Name
cslB
Uniprot ID
Q46079
Uniprot Name
Chondroitinase-B
Molecular Weight
56336.075 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
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
AMY1A
Uniprot ID
P04745
Uniprot Name
Alpha-amylase 1
Molecular Weight
57767.49 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Chloride ion binding
Specific Function
Not Available
Gene Name
AMY2A
Uniprot ID
P04746
Uniprot Name
Pancreatic alpha-amylase
Molecular Weight
57706.51 Da

Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 06:50