NP-MRD: Showing NP-Card for 4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one (NP0222238)

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Record Information

Version

2.0

Created at

2022-09-06 00:01:43 UTC

Updated at

2022-09-06 00:01:43 UTC

NP-MRD ID

NP0222238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one

Description

JGKZMHBGBZTDGW-UHFFFAOYSA- belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one is found in Delisea pulchra. JGKZMHBGBZTDGW-UHFFFAOYSA- is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231517352D          

 15 15  0  0  0  0            999 V2000
   -0.8612    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 Br  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   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 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  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(O)C1=C(Br)C(OC1=O)=C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C9H9Br3O3/c1-2-3-4(13)5-6(10)7(8(11)12)15-9(5)14/h4,13H,2-3H2,1H3

> <INCHI_KEY>
JGKZMHBGBZTDGW-UHFFFAOYSA-N

> <FORMULA>
C9H9Br3O3

> <MOLECULAR_WEIGHT>
404.88

> <EXACT_MASS>
401.810183

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
27.175627246733328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.7111718349999996

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.241283574555656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.130662564489355

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
78.81729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0       3.770   1.651   0.000  0.00  0.00          Br+0
HETATM    9  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       4.267  -1.375   0.000  0.00  0.00          Br+0
HETATM   12 Br   UNK     0       2.109  -2.943   0.000  0.00  0.00          Br+0
HETATM   13  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₉Br₃O₃

Average Mass

404.8800 Da

Monoisotopic Mass

401.81018 Da

IUPAC Name

4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)-2,5-dihydrofuran-2-one

Traditional Name

4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one

CAS Registry Number

Not Available

SMILES

CCCC(O)C1=C(Br)C(OC1=O)=C(Br)Br

InChI Identifier

InChI=1S/C9H9Br3O3/c1-2-3-4(13)5-6(10)7(8(11)12)15-9(5)14/h4,13H,2-3H2,1H3

InChI Key

JGKZMHBGBZTDGW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delisea pulchra	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Enol ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous halide
Carboxylic acid ester
Lactone
Secondary alcohol
Vinyl halide
Vinyl bromide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Bromoalkene
Haloalkene
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organobromide
Organohalogen compound
Organic oxide
Alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.53	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.82 m³·mol⁻¹	ChemAxon
Polarizability	27.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23426365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one (NP0222238)

MOL for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

3D MOL for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

3D SDF for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

3D-SDF for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

PDB for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

3D PDB for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

SMILES for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

INCHI for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

Structure for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)

3D Structure for NP0222238 (4-bromo-5-(dibromomethylidene)-3-(1-hydroxybutyl)furan-2-one)