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Showing NP-Card for 4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one (NP0318649)

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Record Information
Version2.0
Created at2022-09-11 19:15:53 UTC
Updated at2022-09-11 19:15:53 UTC
NP-MRD IDNP0318649
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one
Description4-Bromo-3-butyl-5-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one is found in Delisea pulchra. 4-Bromo-3-butyl-5-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)


  Mrv1533004241515502D          

 15 15  0  0  0  0            999 V2000
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 Br  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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -3.4523   -0.0014   -1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -0.9144   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529   -0.9463    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0109    0.4408    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.3177    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    0.9290   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581    2.1596   -1.4936 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7411    0.5226    0.4520 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3551    1.6662    0.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398   -0.0328   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997   -1.5678   -1.4822 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3332   -0.4682    0.1902 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4906   -0.3711    1.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261   -0.5229    1.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.2789    2.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228   -0.4064   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259    0.0724   -2.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6164    1.0428   -0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3978   -1.9483   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -0.5371    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -1.2470   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.6628    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    1.0973   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4874    0.7524    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351    2.0835    1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332    0.8212   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  8 13  1  0
 13 14  1  0
 14 15  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
M  END
Download

3D SDF for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)


  Mrv1533004241515502D          

 15 15  0  0  0  0            999 V2000
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 Br  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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC1=C(Br)C(O)(OC1=O)C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C9H11Br3O3/c1-2-3-4-5-6(10)9(14,8(11)12)15-7(5)13/h8,14H,2-4H2,1H3

> <INCHI_KEY>
JCYSHOZCQQQZIK-UHFFFAOYSA-N

> <FORMULA>
C9H11Br3O3

> <MOLECULAR_WEIGHT>
406.896

> <EXACT_MASS>
403.825833

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
27.79138251921643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.5353141706666675

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.458054467274241

> <JCHEM_PKA_STRONGEST_BASIC>
-5.222846976014247

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.1098

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)

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PDB for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      -1.651   1.651   0.000  0.00  0.00          Br+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.614   4.689   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0       3.597   2.904   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   13                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)
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SMILES for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)
CCCCC1=C(Br)C(O)(OC1=O)C(Br)Br
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INCHI for NP0318649 (4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one)
InChI=1S/C9H11Br3O3/c1-2-3-4-5-6(10)9(14,8(11)12)15-7(5)13/h8,14H,2-4H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H11Br3O3
Average Mass406.8960 Da
Monoisotopic Mass403.82583 Da
IUPAC Name4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one
Traditional Name4-bromo-3-butyl-5-(dibromomethyl)-5-hydroxyfuran-2-one
CAS Registry NumberNot Available
SMILES
CCCCC1=C(Br)C(O)(OC1=O)C(Br)Br
InChI Identifier
InChI=1S/C9H11Br3O3/c1-2-3-4-5-6(10)9(14,8(11)12)15-7(5)13/h8,14H,2-4H2,1H3
InChI KeyJCYSHOZCQQQZIK-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
Delisea pulchraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Vinylogous halide
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Bromohydrin
    • 

  • Carboxylic acid ester
    • 

  • Halohydrin
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Bromoalkene
    • 

  • Haloalkene
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Vinyl bromide
    • 

  • Vinyl halide
    • 

  • Alkyl halide
    • 

  • Alkyl bromide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organohalogen compound
    • 

  • Organobromide
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP3.6ALOGPS
logP3.54ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.11 m³·mol⁻¹ChemAxon
Polarizability27.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
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 Compound14017701  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]