Bovine Metabolome Database: Showing metabocard for 5-Aminolevulinic acid (BMDB0001149)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:42 UTC

Update Date

2020-05-19 22:01:34 UTC

BMDB ID

BMDB0001149

Secondary Accession Numbers

BMDB01149

Metabolite Identification

Common Name

5-Aminolevulinic acid

Description

5-Aminolevulinic acid, also known as 5-aminolevulinate or 5-amino-4-oxopentanoate, 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. 5-Aminolevulinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Aminolevulinic acid exists in all living species, ranging from bacteria to humans. 5-Aminolevulinic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-ALA	ChEBI
5-Amino-4-oxopentanoate	ChEBI
5-Amino-4-oxovaleric acid	ChEBI
5-Aminolevulinate	ChEBI
Aminolevulinic acid	ChEBI
DALA	ChEBI
delta-ALA	ChEBI
delta-Aminolevulinic acid	ChEBI
5-Amino-4-oxopentanoic acid	Generator
5-Amino-4-oxovalerate	Generator
Aminolevulinate	Generator
Δ-ala	Generator
delta-Aminolevulinate	Generator
Δ-aminolevulinate	Generator
Δ-aminolevulinic acid	Generator
5-Amino-4-oxo-pentanoate	HMDB
5-Amino-4-oxo-pentanoic acid	HMDB
5-Amino-levulinate	HMDB
5-Amino-levulinic acid	HMDB
5-Aminolaevulinate	HMDB
5-Aminolaevulinic acid	HMDB
Aladerm	HMDB
Amino-levulinic acid	HMDB
Kerastick	HMDB
5 Aminolevulinate	HMDB
Acid, Delta-aminolevulinic	HMDB
Levulan	HMDB
5 Aminolaevulinate	HMDB
Acid hydrochloride, aminolevulinic	HMDB
Bertek brand OF aminolevulinic acid hydrochloride	HMDB
Hydrochloride, aminolevulinic acid	HMDB
Acid, aminolevulinic	HMDB
Aminolevulinic acid hydrochloride	HMDB
Delta Aminolevulinic acid	HMDB

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

5-amino-4-oxopentanoic acid

Traditional Name

aminolevulinic acid

CAS Registry Number

106-60-5

SMILES

NCC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)

InChI Key

ZGXJTSGNIOSYLO-UHFFFAOYSA-N

Chemical Taxonomy

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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

delta-amino acid (CHEBI:17549 )
4-oxo monocarboxylic acid (CHEBI:17549 )
Amino fatty acids (LMFA01100055 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	156 - 158 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.8	ALOGPS
logP	-3.3	ChemAxon
logS	0.12	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.45 m³·mol⁻¹	ChemAxon
Polarizability	12.55 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fki-2910000000-12bd38ce6e25c61b8e60	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dr-4900000000-c11a861a1638dd2c20d8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-2911000000-d5b5567862328f5a46cd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-3900000000-538e027ec9932b3f56a5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)	splash10-00di-9500000000-c0d571fa1aa74cf69ea6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)	splash10-00di-9600000000-d0a9f31de64870117dfe	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-00di-1911000000-117a44ade2fd70812e5c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-00dr-2900000000-635a7d4012b9ef5150f9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-2910000000-12bd38ce6e25c61b8e60	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-c11a861a1638dd2c20d8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-2911000000-d5b5567862328f5a46cd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-3900000000-538e027ec9932b3f56a5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9500000000-c0d571fa1aa74cf69ea6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9600000000-d0a9f31de64870117dfe	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-1911000000-117a44ade2fd70812e5c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-2900000000-635a7d4012b9ef5150f9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-b1941f10190ebb6e1343	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05ai-9200000000-6a559cb30668be35a1ed	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-5900000000-cf9a0266243b1a1d0f73	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-995eb11961b16f254be2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fb9-9000000000-64b1ef51cceb8d346f52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-01q9-1900000000-a5686c059e357bc14e96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9300000000-8e219c18bb0fd0837d82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0avr-9000000000-b0d0d9b25a36e5c49f2a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-96cc61ad07db2c38c952	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-9000000000-7b8165e702ac7e6d5f34	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01p9-8900000000-0b739a89ed524e47e3a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-1ffb96adb6268888f722	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-1ffb96adb6268888f722	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01q9-1900000000-a5686c059e357bc14e96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9300000000-8e219c18bb0fd0837d82	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4900000000-1669ed2d77c2a1921a2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0292-9300000000-c07de16859b85d8fb54c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067j-9000000000-316eb66f80f8b40f4ae2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4900000000-1669ed2d77c2a1921a2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0292-9300000000-c07de16859b85d8fb54c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067j-9000000000-316eb66f80f8b40f4ae2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-e2f3aecb5b3f533e4905	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu0-9600000000-fc4f9eaeca47b90745ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-304beef010b4b4fdbb53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-e2f3aecb5b3f533e4905	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu0-9600000000-fc4f9eaeca47b90745ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-304beef010b4b4fdbb53	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Bladder
Epidermis
Fibroblasts
Kidney
Spleen
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Porphyrin Metabolism		Not Available
Glycine and Serine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001149

DrugBank ID

DB00855

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17549

References

Synthesis Reference

Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Delta-aminolevulinic acid dehydratase

General function:: Coenzyme transport and metabolism
Specific function:: Not Available
Gene Name:: ALAD
Uniprot ID:: Q2KIL3
Molecular weight:: 36126.0

Enzyme Details

2. Delta-aminolevulinic acid dehydratase

General function:: Coenzyme transport and metabolism
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 (By similarity).
Gene Name:: ALAD
Uniprot ID:: Q58DK5
Molecular weight:: 36081.0

Reactions

5-Aminolevulinic acid → Porphobilinogen +2 Water	details

Enzyme Details

3. 5-aminolevulinate synthase, nonspecific, mitochondrial

General function:: Coenzyme transport and metabolism
Specific function:: Not Available
Gene Name:: ALAS1
Uniprot ID:: A6QLI6
Molecular weight:: 71062.0

Reactions

Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Carbon dioxide	details
Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Coenzyme A	details

Enzyme Details

4. 5-aminolevulinate synthase, erythroid-specific, mitochondrial

General function:: Coenzyme transport and metabolism
Specific function:: Not Available
Gene Name:: ALAS2
Uniprot ID:: Q3ZC31
Molecular weight:: 65137.0

Enzyme Details

5. Cytoplasmic aconitate hydratase

General function:: Energy production and conversion
Specific function:: Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.
Gene Name:: ACO1
Uniprot ID:: Q0VCU1
Molecular weight:: 98204.0

Showing metabocard for 5-Aminolevulinic acid (BMDB0001149)

Structure for BMDB0001149 (5-Aminolevulinic acid)

Enzymes

Reactions

Reactions