Showing NP-Card for Levulinic acid (NP0001141)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:51 UTC
NP-MRD IDNP0001141
Secondary Accession NumbersNone
Natural Product Identification
Common NameLevulinic acid
DescriptionLevulinic acid is a crystalline keto acid prepared from levulose, inulin, starch, etc., By boiling them with dilute hydrochloric or sulfuric acids.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001141 (Levulinic acid)

  Mrv1652305271900192D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0001141 (Levulinic acid)

HMDB0000720
     RDKit          3D
Levulinic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.4782    0.6087    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    0.0894    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7479   -0.0612    1.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -0.2264   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129   -0.7407    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609    0.2314    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    1.3633    1.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -0.1542    1.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495    1.3864    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    1.0844   -0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2483   -0.1877    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194    0.7048   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -1.0247   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9796   -1.6545    0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -1.0570   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.3621    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0001141 (Levulinic acid)

  Mrv1652305271900192D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001141

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.226704374068705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-oxopentanoic acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.06885744466666677

> <ALOGPS_LOGS>
0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.60659045342587

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.321649025460527

> <JCHEM_PKA_STRONGEST_BASIC>
-7.2827110371620964

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
27.0881

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levulinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001141 (Levulinic acid)

HMDB0000720
     RDKit          3D
Levulinic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.4782    0.6087    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    0.0894    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7479   -0.0612    1.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -0.2264   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129   -0.7407    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609    0.2314    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    1.3633    1.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -0.1542    1.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495    1.3864    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    1.0844   -0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2483   -0.1877    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194    0.7048   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -1.0247   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9796   -1.6545    0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -1.0570   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.3621    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  8 16  1  0
M  END
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PDB for NP0001141 (Levulinic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0001141 (Levulinic acid)

COMPND    HMDB0000720
HETATM    1  C1  UNL     1      -2.478   0.609   0.572  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.110   0.089   0.822  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.748  -0.061   1.964  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.237  -0.226  -0.324  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.113  -0.741   0.093  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.861   0.231   0.921  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.443   1.363   1.253  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.118  -0.154   1.354  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.750   1.386   1.318  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.584   1.084  -0.422  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.248  -0.188   0.662  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.119   0.705  -0.916  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.706  -1.025  -0.947  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.980  -1.655   0.722  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.670  -1.057  -0.811  1.00  0.00           H  
HETATM   16  H8  UNL     1       3.795  -0.362   0.619  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7    8
CONECT    8   16
END
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SMILES for NP0001141 (Levulinic acid)

CC(=O)CCC(O)=O
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INCHI for NP0001141 (Levulinic acid)

InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
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View in JSmol
Synonyms
Chemical FormulaC5H8O3
Average Mass116.1152 Da
Monoisotopic Mass116.04734 Da
IUPAC Name4-oxopentanoic acid
Traditional Namelevulinic acid
CAS Registry Number123-76-2
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 KeyJOOXCMJARBKPKM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 - 33 °CNot Available
Boiling Point245.00 to 246.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility674600 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.49Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility139 g/LALOGPS
logP-0.14ALOGPS
logP-0.069ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.09 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000720
DrugBank IDDB02239
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003296
KNApSAcK IDC00051252
Chemspider ID11091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevulinic_acid
METLIN ID2195
PubChem Compound11579
PDB IDNot Available
ChEBI ID45630
Good Scents IDrw1016791
References
General References
  1. 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 ]
  2. Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome]. Nefrologia. 2004;24 Suppl 3:85-8. [PubMed:15219077 ]
  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 ]
  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 ]
  5. 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 ]
  6. 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 ]