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Showing NP-Card for 4-hydroxy-2-butanone (NP0296180)

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Record Information
Version2.0
Created at2022-09-10 05:37:03 UTC
Updated at2022-09-10 05:37:03 UTC
NP-MRD IDNP0296180
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-2-butanone
Description4-Hydroxybutan-2-one, also known as 3-oxo-1-butanol, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. 4-Hydroxybutan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-hydroxy-2-butanone is found in Glycyrrhiza glabra. 4-hydroxy-2-butanone was first documented in 2010 (PMID: 20924954). A beta-hydroxy ketone that is butan-2-one substituted by a hydroxy group at position 4.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296180 (4-hydroxy-2-butanone)


  Mrv1652310071709482D          

  6  5  0  0  0  0            999 V2000
    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   -1.4289    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
    1.2375   -2.1434    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  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
M  END
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3D MOL for NP0296180 (4-hydroxy-2-butanone)

     RDKit          3D

 14 13  0  0  0  0  0  0  0  0999 V2000
    1.9106   -0.4051    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857    0.5596    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868    1.2709    1.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    0.6995   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061    0.0919   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954   -1.2711    0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8846   -1.1993    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100    0.1012    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.8300   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244    0.2123   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5428    1.7834   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    0.1835   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478    0.6393    0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328   -1.8360   -0.5106 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
  1  7  1  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
M  END
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3D SDF for NP0296180 (4-hydroxy-2-butanone)


  Mrv1652310071709482D          

  6  5  0  0  0  0            999 V2000
    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   -1.4289    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
    1.2375   -2.1434    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  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0296180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3

> <INCHI_KEY>
LVSQXDHWDCMMRJ-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.205995149878689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxybutan-2-one

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-0.4739555013333336

> <ALOGPS_LOGS>
0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.80936456212097

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.798739970032447

> <JCHEM_PKA_STRONGEST_BASIC>
-2.440350303228783

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.5964

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-butanone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0296180 (4-hydroxy-2-butanone)

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PDB for NP0296180 (4-hydroxy-2-butanone)
HEADER    PROTEIN                                 07-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-OCT-17         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310  -4.001   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0296180 (4-hydroxy-2-butanone)
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SMILES for NP0296180 (4-hydroxy-2-butanone)
CC(=O)CCO
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INCHI for NP0296180 (4-hydroxy-2-butanone)
InChI=1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3
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Synonyms
ValueSource
3-oxo-1-ButanolChEBI
3-OxobutanolChEBI
4H2b CompoundMeSH
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
IUPAC Name4-hydroxybutan-2-one
Traditional Name4-hydroxy-2-butanone
CAS Registry NumberNot Available
SMILES
CC(=O)CCO
InChI Identifier
InChI=1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3
InChI KeyLVSQXDHWDCMMRJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycyrrhiza glabraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentBeta-hydroxy ketones  
Alternative Parents
Substituents
  • Beta-hydroxy ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • 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-0.85ALOGPS
logP-0.47ChemAxon
logS0.86ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.6 m³·mol⁻¹ChemAxon
Polarizability9.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0159319  
DrugBank IDDB04094  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound111509  
PDB IDNot Available
ChEBI ID41268  
Good Scents IDNot Available
References
General References
  1. Oh CH, Liu LJ, Hong JH: Design and synthesis of dually branched 5'-norcarbocyclic adenosine phosphonodiester analogue as a new anti-HIV prodrug. Nucleosides Nucleotides Nucleic Acids. 2010 Oct;29(10):721-33. doi: 10.1080/15257770.2010.509645. [PubMed:20924954  ] 
  2. LOTUS database [Link]