NP-MRD: Showing NP-Card for (5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one (NP0306893)

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Record Information

Version

2.0

Created at

2022-09-10 23:39:28 UTC

Updated at

2022-09-10 23:39:29 UTC

NP-MRD ID

NP0306893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one

Description

Rubrolide I belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring. Based on a literature review very few articles have been published on Rubrolide I.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.4772   -3.5979    2.7282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -2.6247    1.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931   -1.7637    1.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876   -0.8654    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701    0.1112   -0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872    0.3899   -0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    0.5986   -1.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    0.9149   -1.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8553    1.0228   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2033    1.3402   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3860    0.8176    0.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6372    1.0096    1.9698 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813    0.5084    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -1.1973    0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -0.4872    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -0.0786    1.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205    0.5858    0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6002    0.8773   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7177    1.5421   -1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030    0.4763   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -0.1977   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1833   -2.2371    1.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283   -3.0371    2.3296 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    0.7416   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454    0.5235   -2.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3624    1.0729   -2.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5537    1.4913   -1.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.3389    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -0.3134    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1859    0.8961    1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052    0.9374   -1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426    0.6989   -2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.4954   -1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 21  1  0
 21 20  2  0
 15 14  1  0
 14 22  2  0
 22 23  1  0
 22  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 20 18  1  0
  4 14  1  0
 13  6  1  0
 19 31  1  0
 17 30  1  0
 16 29  1  0
 21 33  1  0
 20 32  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 13 28  1  0
M  END


  Mrv1652309112201392D          

 23 25  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7679   -2.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884   -2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0733   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938   -2.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378   -3.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -4.3369    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  2  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=C(Cl)C(=O)O\C1=C/C1=CC=C(O)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H10BrClO4/c18-12-7-9(1-6-13(12)21)8-14-15(16(19)17(22)23-14)10-2-4-11(20)5-3-10/h1-8,20-21H/b14-8-

> <INCHI_KEY>
WXCBXFXYLBBMBQ-ZSOIEALJSA-N

> <FORMULA>
C17H10BrClO4

> <MOLECULAR_WEIGHT>
393.62

> <EXACT_MASS>
391.9451

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
34.986778678607095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
4.4264332543333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.048589055090167

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.879407211792213

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9898397703925434

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
92.5315

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.167  -4.358   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.698  -4.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.604  -5.443   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.135  -5.282   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.977  -6.850   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       7.882  -8.096   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      -1.377  -2.739   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
CONECT   14    4   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14    2   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₀BrClO₄

Average Mass

393.6200 Da

Monoisotopic Mass

391.94510 Da

IUPAC Name

(5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)-2,5-dihydrofuran-2-one

Traditional Name

(5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=C(Cl)C(=O)O\C1=C/C1=CC=C(O)C(Br)=C1

InChI Identifier

InChI=1S/C17H10BrClO4/c18-12-7-9(1-6-13(12)21)8-14-15(16(19)17(22)23-14)10-2-4-11(20)5-3-10/h1-8,20-21H/b14-8-

InChI Key

WXCBXFXYLBBMBQ-ZSOIEALJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Carboxylic acid ester
Lactone
Oxacycle
Chloroalkene
Carboxylic acid derivative
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Organochloride
Organohalogen compound
Organobromide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	4.43	ChemAxon
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.53 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	3	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

4582745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5472908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one (NP0306893)

MOL for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

3D MOL for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

3D SDF for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

3D-SDF for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

PDB for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

3D PDB for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

SMILES for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

INCHI for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

Structure for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)

3D Structure for NP0306893 ((5z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-chloro-4-(4-hydroxyphenyl)furan-2-one)