You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:30:30 UTC

HMDB ID

HMDB0000720

Secondary Accession Numbers

HMDB00720

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. Levulinic acid is a sweet, acetoin, and acidic tasting compound. Levulinic acid has been detected, but not quantified in, several different foods, such as fruits, green vegetables, chickens (Gallus gallus), root vegetables, and breakfast cereal. This could make levulinic acid a potential biomarker for the consumption of these foods. Levulinic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Levulinic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Cell

Neuron

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	30 - 33 °C	Not Available
Boiling Point	245.00 to 246.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	674600 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.49	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	139 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.08	31661259
DarkChem	[M-H]-	119.526	31661259
AllCCS	[M+H]+	127.324	32859911
AllCCS	[M-H]-	125.216	32859911
DeepCCS	[M+H]+	123.426	30932474
DeepCCS	[M-H]-	120.652	30932474
DeepCCS	[M-2H]-	157.017	30932474
DeepCCS	[M+Na]+	131.95	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levulinic acid	CC(=O)CCC(O)=O	2266.2	Standard polar	33892256
Levulinic acid	CC(=O)CCC(O)=O	978.2	Standard non polar	33892256
Levulinic acid	CC(=O)CCC(O)=O	1068.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levulinic acid,1TMS,isomer #1	CC(=O)CCC(=O)O[Si](C)(C)C	1136.7	Semi standard non polar	33892256
Levulinic acid,1TMS,isomer #2	CC(=CCC(=O)O)O[Si](C)(C)C	1251.7	Semi standard non polar	33892256
Levulinic acid,1TMS,isomer #3	C=C(CCC(=O)O)O[Si](C)(C)C	1241.3	Semi standard non polar	33892256
Levulinic acid,2TMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1344.8	Semi standard non polar	33892256
Levulinic acid,2TMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1277.7	Standard non polar	33892256
Levulinic acid,2TMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1343.5	Standard polar	33892256
Levulinic acid,2TMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1295.3	Semi standard non polar	33892256
Levulinic acid,2TMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1301.9	Standard non polar	33892256
Levulinic acid,2TMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1371.2	Standard polar	33892256
Levulinic acid,1TBDMS,isomer #1	CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C	1369.4	Semi standard non polar	33892256
Levulinic acid,1TBDMS,isomer #2	CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C	1492.1	Semi standard non polar	33892256
Levulinic acid,1TBDMS,isomer #3	C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C	1465.3	Semi standard non polar	33892256
Levulinic acid,2TBDMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1774.2	Semi standard non polar	33892256
Levulinic acid,2TBDMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1730.8	Standard non polar	33892256
Levulinic acid,2TBDMS,isomer #1	CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1657.1	Standard polar	33892256
Levulinic acid,2TBDMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1718.9	Semi standard non polar	33892256
Levulinic acid,2TBDMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1728.2	Standard non polar	33892256
Levulinic acid,2TBDMS,isomer #2	C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1679.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Levulinic acid GC-MS (1 MEOX; 1 TMS)	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid GC-MS (1 MEOX; 1 TMS)	splash10-0ug0-6900000000-ffad5af79457e68cca02	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid EI-B (Non-derivatized)	splash10-0006-9000000000-dd0d17209893b2b71d10	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid EI-B (Non-derivatized)	splash10-0006-9000000000-0b0447e3daa65b1cd932	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid EI-B (Non-derivatized)	splash10-0006-9000000000-e0d39a4a978220036faa	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid GC-MS (Non-derivatized)	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Levulinic acid GC-MS (Non-derivatized)	splash10-0ug0-6900000000-ffad5af79457e68cca02	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-beecc1bba7b8b0ca4201	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9500000000-8c1e2090296fa71bf0d0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levulinic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00xr-9400000000-923a1fccce36ba18d088	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01vo-9300000000-2c09d37e792efac90655	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0303-9800000000-d158f0c32e82eca0ef90	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid EI-B (HITACHI RMU-7M) , Positive-QTOF	splash10-0006-9000000000-dd0d17209893b2b71d10	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid 20V, Negative-QTOF	splash10-006x-9000000000-adbd744553b432e3c700	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid 40V, Negative-QTOF	splash10-014i-9000000000-469fd98086c8d9ad1830	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levulinic acid 10V, Negative-QTOF	splash10-00di-9200000000-e73b5a48710de1cc7a5d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 10V, Positive-QTOF	splash10-00kb-9400000000-1043277f0ad49a5664a3	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 20V, Positive-QTOF	splash10-006t-9100000000-0a0fca12836c8c8ba113	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 40V, Positive-QTOF	splash10-0zfr-9000000000-247961be84518f0ebcda	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 10V, Negative-QTOF	splash10-014i-3900000000-b8133a0e2c97f98cef46	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 20V, Negative-QTOF	splash10-01b9-9600000000-e133b145c780f2c290d3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 40V, Negative-QTOF	splash10-052e-9000000000-6ff5c46cdc591b725694	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 10V, Negative-QTOF	splash10-00xs-9300000000-eb059cdb2e36fd93dd56	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 20V, Negative-QTOF	splash10-0007-9000000000-1e533a2764dd57c91302	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 40V, Negative-QTOF	splash10-0006-9000000000-c7b0e35a1f31ca5d7853	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 10V, Positive-QTOF	splash10-00ea-9000000000-8e96196fb7b3bcd96a40	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 20V, Positive-QTOF	splash10-0006-9000000000-a8096e58fd006cbfe211	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levulinic acid 40V, Positive-QTOF	splash10-0006-9000000000-83517d34c408e5f9d048	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Neuron

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	6.691 +/- 5.255 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.87 (0.31-1.92) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9869358	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.3 (0.4-2.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.28 (0.33-2.75) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9869358	details
Urine	Detected and Quantified	1.7 (0.6-2.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	8.873 +/- 7.994 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	414.784 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1016791

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)

Download (PDF)

General References

Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome]. Nefrologia. 2004;24 Suppl 3:85-8. [PubMed:15219077 ]
Melgaard B, Clausen J, Rastogi SC: Heavy metal levels and delta-amino-levulinic acid dehydrase levels in peripheral polyneuropathy. Acta Neurol Scand. 1976 Apr;53(4):291-307. [PubMed:178141 ]
Matsui M, Kaji R, Oka N, Nishio T, Kimura J: [Multifocal axonal motor neuropathy associated with anti-ganglioside antibodies]. Rinsho Shinkeigaku. 1992 Oct;32(10):1130-5. [PubMed:1297559 ]
Keithly L, Ferris Wayne G, Cullen DM, Connolly GN: Industry research on the use and effects of levulinic acid: a case study in cigarette additives. Nicotine Tob Res. 2005 Oct;7(5):761-71. [PubMed:16191747 ]
Endo G, Horiguchi S, Kiyota I: Urinary N-acetyl-beta-D-glucosaminidase activity in lead-exposed workers. J Appl Toxicol. 1990 Aug;10(4):235-8. [PubMed:2391405 ]

Showing metabocard for Levulinic acid (HMDB0000720)

MOL for HMDB0000720 (Levulinic acid)

3D MOL for HMDB0000720 (Levulinic acid)

3D SDF for HMDB0000720 (Levulinic acid)

3D-SDF for HMDB0000720 (Levulinic acid)

PDB for HMDB0000720 (Levulinic acid)

3D PDB for HMDB0000720 (Levulinic acid)

SMILES for HMDB0000720 (Levulinic acid)

INCHI for HMDB0000720 (Levulinic acid)

Structure for HMDB0000720 (Levulinic acid)

3D Structure for HMDB0000720 (Levulinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra