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Showing NP-Card for methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate (NP0246496)

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Record Information
Version2.0
Created at2022-09-07 08:00:02 UTC
Updated at2022-09-07 08:00:02 UTC
NP-MRD IDNP0246496
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate
DescriptionMethyl 3-[(2R)-3-bromo-5-oxo-2,5-dihydrofuran-2-yl]propanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate is found in Xestospongia testudinaria. Based on a literature review very few articles have been published on methyl 3-[(2R)-3-bromo-5-oxo-2,5-dihydrofuran-2-yl]propanoate.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)


  Mrv1652309072210002D          

 13 13  0  0  1  0            999 V2000
    0.6725   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -2.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -2.4082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9986   -2.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -2.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180   -3.7807    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
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3D MOL for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.9522   -0.6991    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -0.2757    0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    0.2495    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.3195   -0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.6488    1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    1.1955    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550    0.2329   -0.5692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3536    0.9178   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5399    0.2685   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7196    0.6005   -1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2011   -0.9064   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891   -0.9141    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -2.3275    1.0869 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -0.3480   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8492   -0.2902    0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0645   -1.8109    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -0.1737    1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.4693    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043    1.3793    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507    2.1629   -0.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338   -0.0602   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -1.6386    0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  6
 11 22  1  0
M  END
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3D SDF for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)


  Mrv1652309072210002D          

 13 13  0  0  1  0            999 V2000
    0.6725   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -2.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -2.4082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9986   -2.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -2.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180   -3.7807    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@H]1OC(=O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C8H9BrO4/c1-12-7(10)3-2-6-5(9)4-8(11)13-6/h4,6H,2-3H2,1H3/t6-/m1/s1

> <INCHI_KEY>
YHOUBGRCTWLEFY-ZCFIWIBFSA-N

> <FORMULA>
C8H9BrO4

> <MOLECULAR_WEIGHT>
249.06

> <EXACT_MASS>
247.968422

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.81842080827367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-[(2R)-3-bromo-5-oxo-2,5-dihydrofuran-2-yl]propanoate

> <JCHEM_LOGP>
1.1474050123333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.540099758817873

> <JCHEM_PKA_STRONGEST_BASIC>
-6.642435755611888

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
48.7599

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(2R)-3-bromo-5-oxo-2H-furan-2-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)

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PDB for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.255  -3.725   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.589  -4.495   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.923  -2.185   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.256  -4.495   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.924  -4.495   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.331  -3.869   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.361  -5.013   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.893  -4.852   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.591  -6.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.085  -6.027   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       6.940  -7.057   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)
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SMILES for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)
COC(=O)CC[C@H]1OC(=O)C=C1Br
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INCHI for NP0246496 (methyl 3-[(2r)-3-bromo-5-oxo-2h-furan-2-yl]propanoate)
InChI=1S/C8H9BrO4/c1-12-7(10)3-2-6-5(9)4-8(11)13-6/h4,6H,2-3H2,1H3/t6-/m1/s1
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View in JSmol
Synonyms
ValueSource
Methyl 3-[(2R)-3-bromo-5-oxo-2,5-dihydrofuran-2-yl]propanoic acidGenerator
Chemical FormulaC8H9BrO4
Average Mass249.0600 Da
Monoisotopic Mass247.96842 Da
IUPAC Namemethyl 3-[(2R)-3-bromo-5-oxo-2,5-dihydrofuran-2-yl]propanoate
Traditional Namemethyl 3-[(2R)-3-bromo-5-oxo-2H-furan-2-yl]propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)CC[C@H]1OC(=O)C=C1Br
InChI Identifier
InChI=1S/C8H9BrO4/c1-12-7(10)3-2-6-5(9)4-8(11)13-6/h4,6H,2-3H2,1H3/t6-/m1/s1
InChI KeyYHOUBGRCTWLEFY-ZCFIWIBFSA-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
Xestospongia testudinariaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • 2-furanone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Dihydrofuran
    • 

  • Methyl ester
    • 

  • Vinylogous halide
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Bromoalkene
    • 

  • Haloalkene
    • 

  • Vinyl bromide
    • 

  • Vinyl halide
    • 

  • Organoheterocyclic compound
    • 

  • Carbonyl group
    • 

  • Organohalogen compound
    • 

  • Organobromide
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • 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
logP1.15ChemAxon
pKa (Strongest Acidic)5.54ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.76 m³·mol⁻¹ChemAxon
Polarizability19.82 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 ID27025211  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound51002842  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]