Np mrd loader

Showing NP-Card for (3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one (NP0243400)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-07 03:56:25 UTC
Updated at2022-09-07 03:56:25 UTC
NP-MRD IDNP0243400
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one
Description(3AS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-2,3,3a,7a-tetrahydro-1-benzofuran-2-one belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one is found in Aplysina cauliformis. Based on a literature review very few articles have been published on (3aS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-2,3,3a,7a-tetrahydro-1-benzofuran-2-one.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)


  Mrv1652309072205562D          

 15 16  0  0  1  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5549    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
Download

3D MOL for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.5906    0.0397   -0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436   -0.9494   -0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.5818   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4108   -0.7031   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443   -1.4217   -2.9957 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -0.0237   -1.1034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0299   -0.5480   -1.6614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152    0.2871   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514    0.4352   -1.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400    0.9548    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    0.0100    0.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8802   -1.3018    0.5071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859    0.2060    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -0.0908    1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3575    0.1130    2.3199 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -0.4412   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6874    0.7972   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    0.6062   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    1.0674   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    0.9605    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.9597   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -1.9590   -0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    0.5837    2.2979 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  6
 10 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)


  Mrv1652309072205562D          

 15 16  0  0  1  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5549    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)[C@H]2OC(=O)C[C@]2(O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C9H8Br2O4/c1-14-7-4(10)2-9(13)3-5(12)15-8(9)6(7)11/h2,8,13H,3H2,1H3/t8-,9-/m1/s1

> <INCHI_KEY>
ZIWGLWRAFFMGTG-RKDXNWHRSA-N

> <FORMULA>
C9H8Br2O4

> <MOLECULAR_WEIGHT>
339.967

> <EXACT_MASS>
337.878935

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
23.94035264646785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-2,3,3a,7a-tetrahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
0.34191993200000026

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.944306251079265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6979604457779285

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
61.4555

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)

Download
PDB for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)
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       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0       2.530  -0.237   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.036   5.144   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       5.198   4.383   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Download
3D PDB for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)
Download
SMILES for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)
COC1=C(Br)[C@H]2OC(=O)C[C@]2(O)C=C1Br
Download
INCHI for NP0243400 ((3as,7as)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one)
InChI=1S/C9H8Br2O4/c1-14-7-4(10)2-9(13)3-5(12)15-8(9)6(7)11/h2,8,13H,3H2,1H3/t8-,9-/m1/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC9H8Br2O4
Average Mass339.9670 Da
Monoisotopic Mass337.87894 Da
IUPAC Name(3aS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-2,3,3a,7a-tetrahydro-1-benzofuran-2-one
Traditional Name(3aS,7aS)-5,7-dibromo-3a-hydroxy-6-methoxy-3,7a-dihydro-1-benzofuran-2-one
CAS Registry NumberNot Available
SMILES
COC1=C(Br)[C@H]2OC(=O)C[C@]2(O)C=C1Br
InChI Identifier
InChI=1S/C9H8Br2O4/c1-14-7-4(10)2-9(13)3-5(12)15-8(9)6(7)11/h2,8,13H,3H2,1H3/t8-,9-/m1/s1
InChI KeyZIWGLWRAFFMGTG-RKDXNWHRSA-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
Aplysina cauliformisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
Alternative Parents
Substituents
  • Benzofuran
    • 

  • Gamma butyrolactone
    • 

  • Tertiary alcohol
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Bromoalkene
    • 

  • Haloalkene
    • 

  • Vinyl bromide
    • 

  • Vinyl halide
    • 

  • Organic oxygen compound
    • 

  • Organohalogen compound
    • 

  • Organobromide
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP0.34ChemAxon
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.46 m³·mol⁻¹ChemAxon
Polarizability23.94 ųChemAxon
Number of Rings2ChemAxon
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 ID110595238  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163032999  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]