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Showing NP-Card for Acetoacetic acid (NP0001129)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:49 UTC
NP-MRD IDNP0001129
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetoacetic acid
DescriptionAcetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391 ). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001129 (Acetoacetic acid)

            
  Mrv1652309032023512D          

  7  6  0  0  0  0            999 V2000
    2.0480    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101    0.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.3334    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
  5  7  2  0  0  0  0
M  END
Download

3D MOL for NP0001129 (Acetoacetic acid)

HMDB0000060
     RDKit          3D
Acetoacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.6992    0.3663   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827    0.0218    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466    0.4764    1.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5028   -0.8131    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161   -0.2493   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.0467   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    1.1154   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.4525   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.2860   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    0.1410   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -0.8730    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -1.8617    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5565    0.1260 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  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
M  END
Download

3D SDF for NP0001129 (Acetoacetic acid)

            
  Mrv1652309032023512D          

  7  6  0  0  0  0            999 V2000
    2.0480    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101    0.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.3334    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
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)

> <INCHI_KEY>
WDJHALXBUFZDSR-UHFFFAOYSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.179267520270244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxobutanoic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.0014917456666668494

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.223356862546826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.024917062647246

> <JCHEM_PKA_STRONGEST_BASIC>
-7.473176600242656

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.5389

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001129 (Acetoacetic acid)

HMDB0000060
     RDKit          3D
Acetoacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.6992    0.3663   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827    0.0218    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466    0.4764    1.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5028   -0.8131    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161   -0.2493   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.0467   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    1.1154   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.4525   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.2860   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    0.1410   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -0.8730    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -1.8617    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5565    0.1260 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  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
M  END
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PDB for NP0001129 (Acetoacetic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       3.823   0.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.489   0.949   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.489   2.489   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.155   0.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.178   0.949   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.512   0.179   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.178   2.489   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0001129 (Acetoacetic acid)

COMPND    HMDB0000060
HETATM    1  C1  UNL     1      -1.699   0.366  -0.276  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.683   0.022   0.731  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.847   0.476   1.856  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.503  -0.813   0.487  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.416  -0.249  -0.532  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.962  -1.047  -1.328  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.605   1.115  -0.539  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.955   1.452  -0.306  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.575  -0.286  -0.108  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.323   0.141  -1.320  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.122  -0.873   1.430  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.221  -1.862   0.283  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.253   1.556   0.126  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5   11   12
CONECT    5    6    6    7
CONECT    7   13
END
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SMILES for NP0001129 (Acetoacetic acid)

CC(=O)CC(O)=O
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INCHI for NP0001129 (Acetoacetic acid)

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
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View in JSmol
Synonyms
ValueSource
3-Ketobutanoic acidChEBI
3-Ketobutyric acidChEBI
3-Oxobutanoic acidChEBI
3-Oxobutyric acidChEBI
beta-Ketobutyric acidChEBI
3-KetobutanoateGenerator
3-KetobutyrateGenerator
3-OxobutanoateGenerator
3-OxobutyrateGenerator
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
Β-ketobutyrateGenerator
Β-ketobutyric acidGenerator
AcetoacetateGenerator
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
Acetoacetic acid, sodium saltHMDB
Acetoacetic acid, calcium saltHMDB
Acetoacetic acid, lithium saltHMDB
OxobutyrateHMDB
Sodium acetoacetateHMDB
Chemical FormulaC4H6O3
Average Mass102.0886 Da
Monoisotopic Mass102.03169 Da
IUPAC Name3-oxobutanoic acid
Traditional Nameacetoacetic acid
CAS Registry Number541-50-4
SMILES
CC(=O)CC(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Homo sapiensLOTUS Database
Pseudostellaria heterophyllaLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas putidaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • 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 Point36.5 °CNot Available
Boiling Point237.00 to 239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.467 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility240 g/LALOGPS
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000060
DrugBank IDDB01762
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112157
KNApSAcK IDC00007458
Chemspider ID94
KEGG Compound IDC00164
BioCyc ID3-KETOBUTYRATE
BiGG ID1485291
Wikipedia LinkAcetoacetic_acid
METLIN ID276
PubChem Compound96
PDB IDNot Available
ChEBI ID15344
Good Scents IDrw1468691
References
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed:15627241 ]
  4. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  5. Heller MJ, Adams PW, Orosz CG: Evaluation of an automated method of percent reactive antibody determination. Hum Immunol. 1992 Nov;35(3):179-87. [PubMed:1293081 ]
  6. Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. [PubMed:15982426 ]
  7. Oligny LL, Lough J: Hepatic sinusoidal ectasia. Hum Pathol. 1992 Aug;23(8):953-6. [PubMed:1644440 ]
  8. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [PubMed:6696735 ]
  9. Galey JB, Destree O, Dumats J, Genard S, Tachon P: Protection against oxidative damage by iron chelators: effect of lipophilic analogues and prodrugs of N,N'-bis(3,4,5-trimethoxybenzyl)ethylenediamine- N,N'-diacetic acid (OR10141). J Med Chem. 2000 Apr 6;43(7):1418-21. [PubMed:10753479 ]
  10. Saibara T, Onishi S, Sone J, Yamamoto N, Shimahara Y, Mori K, Ozawa K, Yamamoto Y: Arterial ketone body ratio as a possible indicator for liver transplantation in fulminant hepatic failure. Transplantation. 1991 Apr;51(4):782-6. [PubMed:2014530 ]
  11. Mahowald ML, Handwerger BS, Capertone EM Jr, Douglas SD: A comparative study of procedures for sheep erythrocyte-human-T-lymphocyte rosette formation. J Immunol Methods. 1977;15(3):239-45. [PubMed:404361 ]
  12. Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. [PubMed:9710942 ]
  13. Krejsa CM, Schieven GL: Detection of oxidative stress in lymphocytes using dichlorodihydrofluorescein diacetate. Methods Mol Biol. 2000;99:35-47. [PubMed:10909075 ]
  14. Fritzsche I, Buhrdel P, Melcher R, Bohme HJ: Stability of ketone bodies in serum in dependence on storage time and storage temperature. Clin Lab. 2001;47(7-8):399-403. [PubMed:11499803 ]
  15. Polsky-Fisher SL, Cao H, Lu P, Gibson CR: Effect of cytochromes P450 chemical inhibitors and monoclonal antibodies on human liver microsomal esterase activity. Drug Metab Dispos. 2006 Aug;34(8):1361-6. Epub 2006 May 23. [PubMed:16720683 ]
  16. Fulop M, Murthy V, Michilli A, Nalamati J, Qian Q, Saitowitz A: Serum beta-hydroxybutyrate measurement in patients with uncontrolled diabetes mellitus. Arch Intern Med. 1999 Feb 22;159(4):381-4. [PubMed:10030312 ]
  17. Tanaka Y, Ohdan H, Onoe T, Mitsuta H, Tashiro H, Itamoto T, Asahara T: Low incidence of acute rejection after living-donor liver transplantation: immunologic analyses by mixed lymphocyte reaction using a carboxyfluorescein diacetate succinimidyl ester labeling technique. Transplantation. 2005 May 15;79(9):1262-7. [PubMed:15880082 ]
  18. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
  19. de Araujo Burgos MG, Bion FM, Campos F: [Lactation and alcohol: clinical and nutritional effects]. Arch Latinoam Nutr. 2004 Mar;54(1):25-35. [PubMed:15332353 ]
  20. Walker V, Mills GA, Mellor JM, Langley GJ, Farrant RD: A novel pyrroline-5-carboxylic acid and acetoacetic acid adduct in hyperprolinaemia type II. Clin Chim Acta. 2003 May;331(1-2):7-17. [PubMed:12691858 ]
  21. Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [PubMed:3884391 ]