Identification

Name
Aminolevulinic acid
Accession Number
DB00855  (APRD00793, DB05277)
Type
Small Molecule
Groups
Approved
Description

A compound produced from succinyl-CoA and glycine as an intermediate in heme synthesis. It is used as a photochemotherapy for actinic keratosis. [PubChem]

Structure
Thumb
Synonyms
  • 5-ALA
  • 5-Aminolevulinic acid
  • Aminolevulinic acid
  • dALA
  • δ-ALA
  • δ-aminolevulinic acid
External IDs
EINECS 226-679-5 / NSC 18509
Product Ingredients
IngredientUNIICASInChI Key
Aminolevulinic acid hydrochlorideV35KBM8JGR5451-09-2ZLHFONARZHCSET-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmeluzGel78 mg/gCutaneousBiofrontera Bioscience Gmb H2011-12-14Not applicableEu
AmeluzGel100 mg/gTopicalBiofrontera Inc.2016-08-26Not applicableUs
GliolanPowder, for solution30 mg/mlOralMedac2007-09-07Not applicableEu
GliolanPowder, for solution30 mg/mlOralMedac2007-09-07Not applicableEu
GliolanPowder, for solution30 mg/mlOralMedac2007-09-07Not applicableEu
Levulan KerastickPowder, for solution20 %TopicalDusa Pharmaceuticals Inc2004-06-03Not applicableCanada
Levulan KerastickKitDusa Pharmaceuticals Inc2000-09-04Not applicableUs
International/Other Brands
Gliolan (medac GmbH) / Levulan (DUSA Pharmaceuticals, Inc.)
Categories
UNII
88755TAZ87
CAS number
106-60-5
Weight
Average: 131.1299
Monoisotopic: 131.058243159
Chemical Formula
C5H9NO3
InChI Key
ZGXJTSGNIOSYLO-UHFFFAOYSA-N
InChI
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
IUPAC Name
5-amino-4-oxopentanoic acid
SMILES
NCC(=O)CCC(O)=O

Pharmacology

Indication

Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.

Structured Indications
Pharmacodynamics

The metabolism of aminolevulinic acid (ALA) is the first step in the biochemical pathway resulting in heme synthesis. Aminolevulinic acid is not a photosensitizer, but rather a metabolic precursor of protoporphyrin IX (PpIX), which is a photosensitizer. The synthesis of ALA is normally tightly controlled by feedback inhibition of the enzyme, ALA synthetase, presumably by intracellular heme levels. ALA, when provided to the cell, bypasses this control point and results in the accumulation of PpIX, which is converted into heme by ferrochelatase through the addition of iron to the PpIX nucleus.

Mechanism of action

According to the presumed mechanism of action, photosensitization following application of aminolevulinic acid (ALA) topical solution occurs through the metabolic conversion of ALA to protoporphyrin IX (PpIX), which accumulates in the skin to which aminolevulinic acid has been applied. When exposed to light of appropriate wavelength and energy, the accumulated PpIX produces a photodynamic reaction, a cytotoxic process dependent upon the simultaneous presence of light and oxygen. The absorption of light results in an excited state of the porphyrin molecule, and subsequent spin transfer from PpIX to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Photosensitization of actinic (solar) keratosis lesions using aminolevulinic acid, plus illumination with the BLU-UTM Blue Light Photodynamic Therapy Illuminator (BLU-U), is the basis for aminolevulinic acid photodynamic therapy (PDT).

TargetActionsOrganism
ADelta-aminolevulinic acid dehydratase
inducer
Human
Absorption

Oral bioavailability is 50-60%.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Following topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.

Route of elimination
Not Available
Half life

Mean half-life is 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.

Clearance
Not Available
Toxicity

Solution overdose have not been reported.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Hyperglycinemia, non-ketoticDisease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Porphyria Variegata (PV)Disease
3-Phosphoglycerate dehydrogenase deficiencyDisease
Non Ketotic HyperglycinemiaDisease
Hereditary Coproporphyria (HCP)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Glycine and Serine MetabolismMetabolic
Porphyrin MetabolismMetabolic
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Acute Intermittent PorphyriaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Aminolevulinic acid.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Aminolevulinic acid.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Aminolevulinic acid.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Aminolevulinic acid.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Aminolevulinic acid.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Aminolevulinic acid.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Aminolevulinic acid.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Aminolevulinic acid.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Aminolevulinic acid.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Aminolevulinic acid.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
Porfimer sodiumAminolevulinic acid may increase the photosensitizing activities of Porfimer sodium.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Aminolevulinic acid.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Aminolevulinic acid.Approved, Investigational
VerteporfinAminolevulinic acid may increase the photosensitizing activities of Verteporfin.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Takashi Ebata, Hiroshi Kawakami, Katsuya Matsumoto, Koshi Koseki, Hajime Matsushita, "Method of preparing an acid additional salt of delta-aminolevulinic acid." U.S. Patent US5284973, issued July, 1974.

US5284973
General References
  1. Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ: Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial. Lancet Oncol. 2006 May;7(5):392-401. [PubMed:16648043]
  2. Kennedy JC, Marcus SL, Pottier RH: Photodynamic therapy (PDT) and photodiagnosis (PD) using endogenous photosensitization induced by 5-aminolevulinic acid (ALA): mechanisms and clinical results. J Clin Laser Med Surg. 1996 Oct;14(5):289-304. [PubMed:9612195]
External Links
Human Metabolome Database
HMDB01149
KEGG Compound
C00430
PubChem Compound
137
PubChem Substance
46506856
ChemSpider
134
BindingDB
50240386
ChEBI
17549
ChEMBL
CHEMBL601
Therapeutic Targets Database
DAP000314
PharmGKB
PA10015
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Aminolevulinic_acid
ATC Codes
L01XD04 — Aminolevulinic acid
AHFS Codes
  • 84:92.00
PDB Entries
Not Available
FDA label
Download (195 KB)
MSDS
Download (72.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedDiagnosticNon-Melanomatous Skin Cancer1
1Active Not RecruitingTreatmentHead and Neck Carcinoma / Precancerous Conditions1
1CompletedDiagnosticNeoplasms, Brain1
1CompletedTreatmentHead and Neck Tumors1
1RecruitingDiagnosticNeoplasms, Brain1
1RecruitingTreatmentAnal Carcinoma / Subjects With a Histological or Cytological Diagnosis of High-grade Dysplasia or Carcinoma In-situ1
1TerminatedDiagnosticAstrocytomas / Gliomas1
1TerminatedTreatmentAdult Anaplastic Astrocytoma / Adult Anaplastic Oligodendroglioma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Adult Mixed Glioma / Recurrent Adult Brain Tumor1
1TerminatedTreatmentOral Leukoplakia1
1Unknown StatusDiagnosticNeoplasms, Brain1
1Unknown StatusTreatmentAcne Vulgaris1
1Unknown StatusTreatmentUlcerative Colitis (UC)1
1, 2CompletedNot AvailableNeoplasms, Brain1
1, 2CompletedTreatmentErythroplakia / Leukoplakia1
1, 2RecruitingTreatmentBasal Cell Carcinoma (BCC) / Neoplasms, Basal Cell / Photochemotherapy / Photosensitizing Agents1
1, 2RecruitingTreatmentChronic graft versus host disease in skin / Cutaneous T-Cell Lymphoma, Unspecified1
1, 2RecruitingTreatmentNeoplasms, Brain1
1, 2WithdrawnTreatmentMalignant Neoplasm of Colon1
1, 2WithdrawnTreatmentNeoplasms, Brain1
2Active Not RecruitingTreatmentBasal Cell Carcinoma of the Skin / Nevoid Basal Cell Carcinoma Syndrome1
2CompletedNot AvailableActinic Keratosis (AK)2
2CompletedTreatmentAcne Vulgaris1
2CompletedTreatmentActinic Keratosis (AK)5
2CompletedTreatmentBasal Cell Nevus Syndrome / Gorlin's Syndrome1
2CompletedTreatmentGlioblastomas2
2CompletedTreatmentLeukemias / Malignant Lymphomas1
2CompletedTreatmentNon-Melanomatous Skin Cancer1
2CompletedTreatmentNon-Melanomatous Skin Cancer / Precancerous Conditions1
2Not Yet RecruitingTreatmentRefractory Mycosis Fungoides1
2RecruitingDiagnosticBrain and Central Nervous System Tumors1
2RecruitingTreatmentMalignant Gliomas1
2TerminatedDiagnosticAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor1
2TerminatedTreatmentActinic Keratosis (AK) / Skin Neoplasms1
2TerminatedTreatmentAstrocytomas / Glioblastoma Multiforme / Glioblastomas / Gliomas / Malignant Gliomas1
2Unknown StatusTreatmentNon-Melanomatous Skin Cancer1
2WithdrawnTreatmentBenign Neoplasms, Brain / Brain Cancer / Brain Neoplasms, Benign / Brain Neoplasms, Malignant / Brain Tumor, Primary / Brain Tumor, Recurrent / Glioblastomas / Gliomas / Neoplasms, Brain / Neoplasms, Intracranial / Primary Brain Neoplasms / Primary Malignant Brain Neoplasms / Primary Malignant Brain Tumors1
3Active Not RecruitingTreatmentBasal Cell Carcinoma (BCC)1
3Active Not RecruitingTreatmentGlioblastomas1
3CompletedNot AvailableActinic Keratosis (AK)1
3CompletedDiagnosticBrain Cancer / Brain Tumor, Primary / Cancer of Brain / Neoplasms, Brain / Primary Brain Tumors1
3CompletedDiagnosticTransitional Cell Carcinoma of the Bladder1
3CompletedTreatmentActinic Keratosis (AK)4
3Not Yet RecruitingTreatmentActinic Keratosis (AK)1
3RecruitingTreatmentGliomas1
4Active Not RecruitingTreatmentActinic Keratosis (AK) / Natural Daylight Photodynamic Therapy1
4CompletedTreatmentActinic Keratoses (gr I-III) / Multiple Actinic Keratoses1
4CompletedTreatmentActinic Keratosis (AK)1
4Not Yet RecruitingTreatmentActinic Cheilitis1
4RecruitingTreatmentActinic Keratosis (AK)1
4RecruitingTreatmentHutchinson's Melanotic Freckle1
4RecruitingTreatmentPapulopustular Rosacea / Rosaceas1
4TerminatedTreatmentActinic Keratosis (AK)1
Not AvailableActive Not RecruitingTreatmentBasal Cell Nevus Syndrome1
Not AvailableCompletedTreatmentActinic Keratosis (AK)2
Not AvailableNot Yet RecruitingTreatmentActinic Keratosis (AK) / Non-Melanoma Skin Cancer (NMSC)1
Not AvailableNot Yet RecruitingTreatmentSquamous Cell Carcinoma (SCC)1
Not AvailableRecruitingDiagnosticGliomas1
Not AvailableRecruitingTreatmentActinic Keratosis (AK)1
Not AvailableRecruitingTreatmentGlioblastomas1
Not AvailableRecruitingTreatmentSeborrheic Dermatitis1
Not AvailableTerminatedTreatmentPrecancerous/Nonmalignant Condition1

Pharmacoeconomics

Manufacturers
  • Dusa pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
GelCutaneous78 mg/g
GelTopical100 mg/g
Powder, for solutionOral30 mg/ml
Kit
Powder, for solutionTopical20 %
Prices
Unit descriptionCostUnit
Levulan kerastick170.25USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5422093No1992-07-282009-07-28Us
US5954703No1997-10-312017-10-31Us
US6709446No1998-05-012018-05-01Us
US7723910No1999-06-172019-06-17Us
US8216289No1998-05-012018-05-01Us
US8758418No1998-05-012018-05-01Us
US6559183No1999-11-122019-11-12Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)156-158 °CNot Available
water solubilityVery solubleNot Available
logP-1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility173.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.3ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m3·mol-1ChemAxon
Polarizability12.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9162
Blood Brain Barrier+0.7482
Caco-2 permeable-0.7802
P-glycoprotein substrateNon-substrate0.6653
P-glycoprotein inhibitor INon-inhibitor0.9515
P-glycoprotein inhibitor IINon-inhibitor0.7522
Renal organic cation transporterNon-inhibitor0.9017
CYP450 2C9 substrateNon-substrate0.8819
CYP450 2D6 substrateNon-substrate0.8314
CYP450 3A4 substrateNon-substrate0.7939
CYP450 1A2 substrateNon-inhibitor0.9219
CYP450 2C9 inhibitorNon-inhibitor0.9561
CYP450 2D6 inhibitorNon-inhibitor0.9608
CYP450 2C19 inhibitorNon-inhibitor0.9406
CYP450 3A4 inhibitorNon-inhibitor0.9187
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9784
Ames testNon AMES toxic0.8884
CarcinogenicityNon-carcinogens0.8377
BiodegradationReady biodegradable0.9445
Rat acute toxicity1.1726 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9186
hERG inhibition (predictor II)Non-inhibitor0.8944
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) (3 TMS)GC-MSsplash10-0fki-2910000000-12bd38ce6e25c61b8e60
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00dr-4900000000-c11a861a1638dd2c20d8
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00dr-2911000000-d5b5567862328f5a46cd
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00dr-3900000000-538e027ec9932b3f56a5
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)GC-MSsplash10-00di-9500000000-c0d571fa1aa74cf69ea6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)GC-MSsplash10-00di-9600000000-d0a9f31de64870117dfe
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-00di-1911000000-117a44ade2fd70812e5c
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-00dr-2900000000-635a7d4012b9ef5150f9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fki-2910000000-12bd38ce6e25c61b8e60
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-4900000000-c11a861a1638dd2c20d8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-2911000000-d5b5567862328f5a46cd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-3900000000-538e027ec9932b3f56a5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9500000000-c0d571fa1aa74cf69ea6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9600000000-d0a9f31de64870117dfe
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1911000000-117a44ade2fd70812e5c
GC-MS Spectrum - GC-MSGC-MSsplash10-00dr-2900000000-635a7d4012b9ef5150f9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udi-5900000000-cf9a0266243b1a1d0f73
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-995eb11961b16f254be2
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0fb9-9000000000-64b1ef51cceb8d346f52
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-01q9-1900000000-a5686c059e357bc14e96
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-9300000000-8e219c18bb0fd0837d82
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0avr-9000000000-b0d0d9b25a36e5c49f2a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-9000000000-96cc61ad07db2c38c952
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a4i-9000000000-7b8165e702ac7e6d5f34
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01p9-8900000000-0b739a89ed524e47e3a2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-1ffb96adb6268888f722
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-1669ed2d77c2a1921a2d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0292-9300000000-c07de16859b85d8fb54c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067j-9000000000-316eb66f80f8b40f4ae2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-1669ed2d77c2a1921a2d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0292-9300000000-c07de16859b85d8fb54c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067j-9000000000-316eb66f80f8b40f4ae2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-e2f3aecb5b3f533e4905
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bu0-9600000000-fc4f9eaeca47b90745ae
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-304beef010b4b4fdbb53
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-e2f3aecb5b3f533e4905
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bu0-9600000000-fc4f9eaeca47b90745ae
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-304beef010b4b4fdbb53
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-1ffb96adb6268888f722
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-1900000000-a5686c059e357bc14e96
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9300000000-8e219c18bb0fd0837d82
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0avr-9000000000-1815084304ee39158706
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-aa34f5a936aed90b0dcf
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-7b8165e702ac7e6d5f34
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01p9-8900000000-0b739a89ed524e47e3a2
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 delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Delta amino acids and derivatives
Alternative Parents
Gamma-keto acids and derivatives / Short-chain keto acids and derivatives / Alpha-amino ketones / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Delta amino acid or derivatives / Gamma-keto acid / Short-chain keto acid / Keto acid / Alpha-aminoketone / Amino acid / Ketone / Carboxylic acid / Monocarboxylic acid or derivatives / Organonitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
delta-amino acid, 4-oxo monocarboxylic acid (CHEBI:17549) / Amino fatty acids (LMFA01100055)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Zinc ion binding
Specific Function
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name
ALAD
Uniprot ID
P13716
Uniprot Name
Delta-aminolevulinic acid dehydratase
Molecular Weight
36294.485 Da
References
  1. Sakai T: Biomarkers of lead exposure. Ind Health. 2000 Apr;38(2):127-42. [PubMed:10812836]
  2. Vajpayee P, Tripathi RD, Rai UN, Ali MB, Singh SN: Chromium (VI) accumulation reduces chlorophyll biosynthesis, nitrate reductase activity and protein content in Nymphaea alba L. Chemosphere. 2000 Oct;41(7):1075-82. [PubMed:10879826]
  3. Tomas-Zapico C, Martinez-Fraga J, Rodriguez-Colunga MJ, Tolivia D, Hardeland R, Coto-Montes A: Melatonin protects against delta-aminolevulinic acid-induced oxidative damage in male Syrian hamster Harderian glands. Int J Biochem Cell Biol. 2002 May;34(5):544-53. [PubMed:11906825]
  4. Frere F, Schubert WD, Stauffer F, Frankenberg N, Neier R, Jahn D, Heinz DW: Structure of porphobilinogen synthase from Pseudomonas aeruginosa in complex with 5-fluorolevulinic acid suggests a double Schiff base mechanism. J Mol Biol. 2002 Jul 5;320(2):237-47. [PubMed:12079382]
  5. Flora SJ, Kannan GM, Pant BP, Jaiswal DK: Combined administration of oxalic acid, succimer and its analogue for the reversal of gallium arsenide-induced oxidative stress in rats. Arch Toxicol. 2002 Jun;76(5-6):269-76. Epub 2002 Apr 23. [PubMed:12107644]
  6. Akagi R, Yasui Y, Harper P, Sassa S: A novel mutation of delta-aminolaevulinate dehydratase in a healthy child with 12% erythrocyte enzyme activity. Br J Haematol. 1999 Sep;106(4):931-7. [PubMed:10519994]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Terada T, Sawada K, Irie M, Saito H, Hashimoto Y, Inui K: Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2. Pflugers Arch. 2000 Sep;440(5):679-84. [PubMed:11007306]
  2. Doring F, Walter J, Will J, Focking M, Boll M, Amasheh S, Clauss W, Daniel H: Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications. J Clin Invest. 1998 Jun 15;101(12):2761-7. [PubMed:9637710]
  3. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Doring F, Walter J, Will J, Focking M, Boll M, Amasheh S, Clauss W, Daniel H: Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications. J Clin Invest. 1998 Jun 15;101(12):2761-7. [PubMed:9637710]
  2. Terada T, Sawada K, Irie M, Saito H, Hashimoto Y, Inui K: Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2. Pflugers Arch. 2000 Sep;440(5):679-84. [PubMed:11007306]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:47