Bovine Metabolome Database: Showing metabocard for Levulinic acid (BMDB0000720)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:28 UTC

Update Date

2020-05-11 20:29:29 UTC

BMDB ID

BMDB0000720

Secondary Accession Numbers

BMDB00720

Metabolite Identification

Common Name

Levulinic acid

Description

Levulinic acid, also known as laevulinsaeure or levulate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Levulinic acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Levulinic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Acetylpropionic acid	ChEBI
3-Ketobutane-1-carboxylic acid	ChEBI
4-Ketovaleric acid	ChEBI
4-Oxovaleric acid	ChEBI
beta-Acetylpropionic acid	ChEBI
gamma-Ketovaleric acid	ChEBI
LAEVULINIC ACID	ChEBI
Laevulinsaeure	ChEBI
LEVA	ChEBI
Levulic acid	ChEBI
Levulinsaeure	ChEBI
3-Acetylpropionate	Generator
3-Ketobutane-1-carboxylate	Generator
4-Ketovalerate	Generator
4-Oxovalerate	Generator
b-Acetylpropionate	Generator
b-Acetylpropionic acid	Generator
beta-Acetylpropionate	Generator
Β-acetylpropionate	Generator
Β-acetylpropionic acid	Generator
g-Ketovalerate	Generator
g-Ketovaleric acid	Generator
gamma-Ketovalerate	Generator
Γ-ketovalerate	Generator
Γ-ketovaleric acid	Generator
LAEVULINate	Generator
Levulate	Generator
Levulinate	Generator
4-Oxopentanoate	HMDB
4-Oxopentanoic acid	HMDB
Diasporal	HMDB
Levulinic acid, sodium salt	HMDB
Magnesium diasporal	HMDB
Calcium levulate	HMDB
Magnesium levulinate	HMDB
Calcium levulinate	HMDB
Levulinic acid, ammonium salt	HMDB
Levulinic acid, calcium salt	HMDB
Magnesium laevulinate	HMDB
Levulinic acid	ChEBI

Chemical Formula

C₅H₈O₃

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

IUPAC Name

4-oxopentanoic acid

Traditional Name

levulinic acid

CAS Registry Number

123-76-2

SMILES

CC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)

InChI Key

JOOXCMJARBKPKM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Short-chain keto acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxopentanoic acid (CHEBI:45630 )
straight-chain saturated fatty acid (CHEBI:45630 )
Oxo fatty acids (LMFA01060006 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	30 - 33 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.49	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.14	ALOGPS
logP	-0.069	ChemAxon
logS	0.08	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.09 m³·mol⁻¹	ChemAxon
Polarizability	11.23 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-MS (1 MEOX; 1 TMS)	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0ug0-6900000000-ffad5af79457e68cca02	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-dd0d17209893b2b71d10	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-0b0447e3daa65b1cd932	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e0d39a4a978220036faa	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ug0-6900000000-ffad5af79457e68cca02	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-beecc1bba7b8b0ca4201	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9500000000-8c1e2090296fa71bf0d0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00xr-9400000000-923a1fccce36ba18d088	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01vo-9300000000-2c09d37e792efac90655	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0303-9800000000-d158f0c32e82eca0ef90	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-dd0d17209893b2b71d10	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9000000000-adbd744553b432e3c700	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-469fd98086c8d9ad1830	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9200000000-e73b5a48710de1cc7a5d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-9400000000-1043277f0ad49a5664a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-9100000000-0a0fca12836c8c8ba113	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9000000000-247961be84518f0ebcda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-b8133a0e2c97f98cef46	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9600000000-e133b145c780f2c290d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-9000000000-6ff5c46cdc591b725694	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xs-9300000000-eb059cdb2e36fd93dd56	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9000000000-1e533a2764dd57c91302	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c7b0e35a1f31ca5d7853	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ea-9000000000-8e96196fb7b3bcd96a40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-a8096e58fd006cbfe211	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-83517d34c408e5f9d048	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, 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
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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Neuron

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000720

DrugBank ID

DB02239

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003296

KNApSAcK ID

C00051252

Chemspider ID

11091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levulinic_acid

METLIN ID

2195

PubChem Compound

11579

PDB ID

Not Available

ChEBI ID

45630

References

Synthesis Reference

Cai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong. Review on preparation methods of levulinic acid, a new platform chemical. Xiandai Huagong (2003), 23(4), 14-16.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Levulinic acid (BMDB0000720)

Structure for BMDB0000720 (Levulinic acid)