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Human Metabolome Database Version 3.5

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Showing metabocard for Levulinic acid (HMDB00720)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:10 -0700
HMDB ID HMDB00720
Secondary Accession Numbers None
Metabolite Identification
Common Name Levulinic acid
Description Levulinic acid is a crystalline keto acid prepared from levulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulfuric acids.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Acetylpropionate
  2. 3-Acetylpropionic acid
  3. 4-Ketovalerate
  4. 4-Ketovaleric acid
  5. 4-Oxopentanoate
  6. 4-Oxopentanoic acid
  7. 4-Oxovalerate
  8. 4-Oxovaleric acid
  9. b-Acetylpropionate
  10. b-Acetylpropionic acid
  11. beta-Acetylpropionate
  12. beta-Acetylpropionic acid
  13. g-Ketovalerate
  14. g-Ketovaleric acid
  15. gamma-Ketovalerate
  16. gamma-Ketovaleric acid
  17. Laevulinate
  18. Laevulinic acid
  19. Levulate
  20. Levulic acid
  21. Levulinate
  22. Levulinic acid
Chemical Formula C5H8O3
Average Molecular Weight 116.1152
Monoisotopic Molecular Weight 116.047344122
IUPAC Name 4-oxopentanoic acid
Traditional IUPAC Name laevulinic 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
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Keto-Acids and Derivatives
Sub Class Gamma Keto-Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Oxo fatty acids(Lipidmaps)
  • Straight Chain Fatty Acids
  • oxopentanoic acid(ChEBI)
  • straight-chain saturated fatty acid anion(ChEBI)
Substituents
  • Carboxylic Acid
  • Ketone
  • Short Chain Keto Acid
Direct Parent Gamma Keto-Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Liquid
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
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
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 27.09 ChemAxon
Polarizability 11.22 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Neuron
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
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0.87 (0.31-1.92) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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1.3 (0.4-2.0) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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1.28 (0.33-2.75) umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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1.7 (0.6-2.5) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB003296
KNApSAcK ID Not Available
Chemspider ID 11091 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Levulinic acid Link_out
NuGOwiki Link HMDB00720 Link_out
Metagene Link HMDB00720 Link_out
METLIN ID 2195 Link_out
PubChem Compound 11579 Link_out
PDB ID SHF Link_out
ChEBI ID 45630 Link_out
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
  1. Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome] Nefrologia. 2004;24 Suppl 3:85-8. Pubmed: 15219077 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out