NP-MRD: Showing NP-Card for (1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate (NP0168375)

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Record Information

Version

2.0

Created at

2022-09-03 04:10:03 UTC

Updated at

2022-09-03 04:10:04 UTC

NP-MRD ID

NP0168375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate

Description

CHEMBL496439 belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate is found in Delisea pulchra. Based on a literature review very few articles have been published on CHEMBL496439.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.9066   -1.0902    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869   -2.0232   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.6493    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382   -0.2886   -0.2781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8192    0.7782    0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3161    1.7267   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    2.8680   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0643    1.6206   -1.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3391   -0.1611    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4316    0.0509   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153    0.2576   -2.2694 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    0.1044    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8022    0.3002    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1684    0.3289    1.9209 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.0874    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.2609    1.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -0.4580    2.7084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.5343    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531   -0.3622   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185   -1.6537    0.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1243   -3.0772   -0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -1.9568   -1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -2.4509   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588   -1.7023    1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439   -0.2142   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6243    3.2905    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497    3.6577   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1711    2.5432    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424    0.4433   -0.6904 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  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 12 13  2  0
 13 14  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  6
  7 26  1  0
  7 27  1  0
  7 28  1  0
 13 29  1  0
M  END


  Mrv1652309032206102D          

 17 17  0  0  1  0            999 V2000
    1.3870   -1.5832    0.0000 C   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   -2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -3.2332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5304   -2.8207    0.0000 O   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
    2.8159   -1.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -1.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -4.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -4.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -4.2882    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2284   -5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134   -5.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3778   -6.7489    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034   -5.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -4.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639   -4.2882    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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  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
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0168375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](OC(C)=O)C1=C(Br)\C(OC1=O)=C\I

> <INCHI_IDENTIFIER>
InChI=1S/C11H12BrIO4/c1-3-4-7(16-6(2)14)9-10(12)8(5-13)17-11(9)15/h5,7H,3-4H2,1-2H3/b8-5-/t7-/m1/s1

> <INCHI_KEY>
PQGNPRSFFPSLLF-BESBCXERSA-N

> <FORMULA>
C11H12BrIO4

> <MOLECULAR_WEIGHT>
415.021

> <EXACT_MASS>
413.89637

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
30.364830190529933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[(5Z)-4-bromo-5-(iodomethylidene)-2-oxo-2,5-dihydrofuran-3-yl]butyl acetate

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.6632556523333326

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.777038919482612

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
75.8241

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[(5Z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.589  -2.955   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.923  -5.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.256  -6.035   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.590  -5.265   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.256  -2.955   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.924  -2.955   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.256  -7.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.502  -8.481   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       7.967  -8.005   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       6.026  -9.945   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.932 -11.191   0.000  0.00  0.00           C+0
HETATM   14  I   UNK     0       6.305 -12.598   0.000  0.00  0.00           I+0
HETATM   15  O   UNK     0       4.486  -9.945   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.011  -8.481   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.546  -8.005   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂BrIO₄

Average Mass

415.0210 Da

Monoisotopic Mass

413.89637 Da

IUPAC Name

(1R)-1-[(5Z)-4-bromo-5-(iodomethylidene)-2-oxo-2,5-dihydrofuran-3-yl]butyl acetate

Traditional Name

(1R)-1-[(5Z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate

CAS Registry Number

Not Available

SMILES

CCC[C@@H](OC(C)=O)C1=C(Br)\C(OC1=O)=C\I

InChI Identifier

InChI=1S/C11H12BrIO4/c1-3-4-7(16-6(2)14)9-10(12)8(5-13)17-11(9)15/h5,7H,3-4H2,1-2H3/b8-5-/t7-/m1/s1

InChI Key

PQGNPRSFFPSLLF-BESBCXERSA-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
Dicarboxylic acid or derivatives
Enol ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous halide
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Iodoalkene
Vinyl bromide
Vinyl halide
Vinyl iodide
Bromoalkene
Haloalkene
Organohalogen compound
Organobromide
Organoiodide
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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	3.47	ALOGPS
logP	2.66	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.82 m³·mol⁻¹	ChemAxon
Polarizability	30.36 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

10318806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21729104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate (NP0168375)

MOL for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

3D MOL for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

3D SDF for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

3D-SDF for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

PDB for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

3D PDB for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

SMILES for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

INCHI for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

Structure for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)

3D Structure for NP0168375 ((1r)-1-[(5z)-4-bromo-5-(iodomethylidene)-2-oxofuran-3-yl]butyl acetate)