Showing NP-Card for 3-Hydroxy-2-pentanone (NP0047273)

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Record Information
Version2.0
Created at2022-03-17 20:37:26 UTC
Updated at2022-03-17 20:37:27 UTC
NP-MRD IDNP0047273
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxy-2-pentanone
Description3-Hydroxy-2-pentanone, also known as 2-oxo-3-pentanol or acetylethylcarbinol, belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thus, 3-hydroxy-2-pentanone is considered to be an oxygenated hydrocarbon lipid molecule. 3-Hydroxy-2-pentanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxy-2-pentanone is a herbal and truffle tasting compound. Outside of the human body, 3-Hydroxy-2-pentanone has been detected, but not quantified in, asparagus. 3-Hydroxy-2-pentanone is found in Corynebacterium glutamicum. This could make 3-hydroxy-2-pentanone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047273 (3-Hydroxy-2-pentanone)

  Mrv0541 05061311582D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for NP0047273 (3-Hydroxy-2-pentanone)

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3D SDF for NP0047273 (3-Hydroxy-2-pentanone)
  Mrv0541 05061311582D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3

> <INCHI_KEY>
HDKKRASBPHFULQ-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.028899769273636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxypentan-2-one

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
0.3803183996666666

> <ALOGPS_LOGS>
0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.806098885186675

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.427875887356581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.486414571764441

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.9149

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxypentan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047273 (3-Hydroxy-2-pentanone)
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PDB for NP0047273 (3-Hydroxy-2-pentanone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    5    6                                                  
CONECT    5    3    4    7                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0047273 (3-Hydroxy-2-pentanone)
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SMILES for NP0047273 (3-Hydroxy-2-pentanone)
CCC(O)C(C)=O
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INCHI for NP0047273 (3-Hydroxy-2-pentanone)
InChI=1S/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3
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Synonyms
ValueSource
2-oxo-3-PentanolHMDB
AcetylethylcarbinolHMDB
FEMA 3550HMDB
3-Hydroxy-2-pentanoneMeSH
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name3-hydroxypentan-2-one
Traditional Name3-hydroxypentan-2-one
CAS Registry Number3142-66-3
SMILES
CCC(O)C(C)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3
InChI KeyHDKKRASBPHFULQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Corynebacterium glutamicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAcyloins  
Alternative Parents
Substituents
  • Acyloin
    • 

  • Alpha-hydroxy ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.1ALOGPS
logP0.38ChemAxon
logS0.44ALOGPS
pKa (Strongest Acidic)13.43ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.91 m³·mol⁻¹ChemAxon
Polarizability11.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031516  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008110  
KNApSAcK IDNot Available
Chemspider ID56264  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62484  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available