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5-Aminolevulinic acid (FDB022452)

Record Information
Version1.0
Creation date2011-09-21 00:14:15 UTC
Update date2019-11-26 03:21:03 UTC
Primary IDFDB022452
Secondary Accession Numbers
  • FDB030562
Chemical Information
FooDB Name5-Aminolevulinic acid
DescriptionAn intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway. 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. [HMDB]. 5-Aminolevulinic acid is found in many foods, some of which are fireweed, chia, sesbania flower, and taro.
CAS Number106-60-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility173 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m³·mol⁻¹ChemAxon
Polarizability12.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9NO3
IUPAC name5-amino-4-oxopentanoic acid
InChI IdentifierInChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChI KeyZGXJTSGNIOSYLO-UHFFFAOYSA-N
Isomeric SMILESNCC(=O)CCC(O)=O
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
Classification
Description Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
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
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5-Aminolevulinic acid, 3 TMS, GC-MS Spectrumsplash10-0fki-2910000000-12bd38ce6e25c61b8e60Spectrum
GC-MS5-Aminolevulinic acid, 3 TMS, GC-MS Spectrumsplash10-00dr-4900000000-c11a861a1638dd2c20d8Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-2911000000-d5b5567862328f5a46cdSpectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-3900000000-538e027ec9932b3f56a5Spectrum
GC-MS5-Aminolevulinic acid, 3 TMS; 1 MEOX, GC-MS Spectrumsplash10-00di-9500000000-c0d571fa1aa74cf69ea6Spectrum
GC-MS5-Aminolevulinic acid, 3 TMS; 1 MEOX, GC-MS Spectrumsplash10-00di-9600000000-d0a9f31de64870117dfeSpectrum
GC-MS5-Aminolevulinic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-00di-1911000000-117a44ade2fd70812e5cSpectrum
GC-MS5-Aminolevulinic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-00dr-2900000000-635a7d4012b9ef5150f9Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-0fki-2910000000-12bd38ce6e25c61b8e60Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-c11a861a1638dd2c20d8Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-2911000000-d5b5567862328f5a46cdSpectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-3900000000-538e027ec9932b3f56a5Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9500000000-c0d571fa1aa74cf69ea6Spectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9600000000-d0a9f31de64870117dfeSpectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00di-1911000000-117a44ade2fd70812e5cSpectrum
GC-MS5-Aminolevulinic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-2900000000-635a7d4012b9ef5150f9Spectrum
Predicted GC-MS5-Aminolevulinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-b1941f10190ebb6e1343Spectrum
Predicted GC-MS5-Aminolevulinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05ai-9200000000-6a559cb30668be35a1edSpectrum
Predicted GC-MS5-Aminolevulinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-5900000000-cf9a0266243b1a1d0f732012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-995eb11961b16f254be22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-64b1ef51cceb8d346f522012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-1900000000-a5686c059e357bc14e962012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9300000000-8e219c18bb0fd0837d822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0avr-9000000000-b0d0d9b25a36e5c49f2a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-96cc61ad07db2c38c9522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-7b8165e702ac7e6d5f342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01p9-8900000000-0b739a89ed524e47e3a22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-1ffb96adb6268888f7222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-1ffb96adb6268888f7222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01q9-1900000000-a5686c059e357bc14e962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9300000000-8e219c18bb0fd0837d822017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2d2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54c2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae22015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2d2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54c2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae22015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e49052015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745ae2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb532015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e49052015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745ae2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb532015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID134
ChEMBL IDCHEMBL601
KEGG Compound IDC00430
Pubchem Compound ID137
Pubchem Substance IDNot Available
ChEBI ID17549
Phenol-Explorer IDNot Available
DrugBank IDDB00855
HMDB IDHMDB01149
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDDELTA-AMINO-LEVULINIC-ACID
BIGG ID34963
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5-Aminolevulinic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
dermal50177 A drug used to treat or prevent skin disorders or for the routine care of skin.CHEBI
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).