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Showing NP-Card for (r)-acetoin (NP0287401)

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Record Information
Version2.0
Created at2022-09-09 16:27:39 UTC
Updated at2022-09-09 16:27:39 UTC
NP-MRD IDNP0287401
Secondary Accession NumbersNone
Natural Product Identification
Common Name(r)-acetoin
Description(R)-acetoin, also known as (R)-dimethylketol, 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, (R)-acetoin is considered to be an oxygenated hydrocarbon lipid molecule (R)-acetoin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-acetoin exists in both E. (r)-acetoin is found in Corynebacterium glutamicum and Streptomyces avermitilis. Coli (prokaryote) and yeast (eukaryote).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0287401 ((r)-acetoin)


  Mrv0541 09181201332D          

  6  5  0  0  0  0            999 V2000
   -4.5302    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
M  END
Download

3D MOL for NP0287401 ((r)-acetoin)

     RDKit          3D

 14 13  0  0  0  0  0  0  0  0999 V2000
    1.8213   -0.1375   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400    0.6742    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867    1.6185    1.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126    0.3613   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0876   -1.0518    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.2776    0.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887   -0.0290   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -1.2037    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068    0.1760    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.3886   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0935   -1.0021    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3420   -1.4127    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409   -1.7165   -0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    2.0571   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 11  1  0
  5 12  1  0
  5 13  1  0
  4 10  1  6
  6 14  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
M  END
Download

3D SDF for NP0287401 ((r)-acetoin)


  Mrv0541 09181201332D          

  6  5  0  0  0  0            999 V2000
   -4.5302    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m1/s1

> <INCHI_KEY>
ROWKJAVDOGWPAT-GSVOUGTGSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.109409699439318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxybutan-2-one

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-0.1422039953333334

> <ALOGPS_LOGS>
0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.81975350602122

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.723456226493909

> <JCHEM_PKA_STRONGEST_BASIC>
-3.357098011793852

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.390900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-acetoin

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0287401 ((r)-acetoin)

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PDB for NP0287401 ((r)-acetoin)
HEADER    PROTEIN                                 18-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-12         0                                  
HETATM    1  C   UNK     0      -8.456  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.123   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.789  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.455   9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.123   7.700   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.789  11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

Download
3D PDB for NP0287401 ((r)-acetoin)
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SMILES for NP0287401 ((r)-acetoin)
C[C@@H](O)C(C)=O
Download
INCHI for NP0287401 ((r)-acetoin)
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m1/s1
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View in JSmol
Synonyms
ValueSource
(R)-2-AcetoinChEBI
(R)-3-Hydroxy-2-butanoneChEBI
(R)-3-Hydroxybutan-2-oneChEBI
(R)-DimethylketolChEBI
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
IUPAC Name(3R)-3-hydroxybutan-2-one
Traditional Name(R)-acetoin
CAS Registry NumberNot Available
SMILES
C[C@@H](O)C(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m1/s1
InChI KeyROWKJAVDOGWPAT-GSVOUGTGSA-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
Corynebacterium glutamicumLOTUS Database
Streptomyces avermitilisLOTUS 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-0.66ALOGPS
logP-0.14ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability9.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04364  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008099  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00810  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439314  
PDB IDNot Available
ChEBI ID15686  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]