NP-MRD: Showing NP-Card for 4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one (NP0298050)

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Record Information

Version

2.0

Created at

2022-09-10 08:57:13 UTC

Updated at

2022-09-10 08:57:13 UTC

NP-MRD ID

NP0298050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3'-Bromorubrolide F belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one was first documented in 2012 (PMID: 23030848). Based on a literature review very few articles have been published on 3'-Bromorubrolide F (PMID: 30733455).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    6.6917    0.2149   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938   -0.8029   -0.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183   -0.6454   -0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -1.7188    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2565   -1.5846    0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592   -0.3637    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934   -0.2402    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819    0.4808   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981    1.1586   -1.7020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352    1.8246   -2.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921    2.5437   -3.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092    1.5576   -1.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    0.7569   -0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0008    0.2757    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9657   -0.3091    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -0.8021    1.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542   -0.7143    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5045   -1.2024    1.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4125   -0.1231    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1272    0.0088   -0.7471 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859    0.3548   -0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.6881   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8502    0.5626   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689   -0.2298   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3205    0.8821   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9277    0.7992    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -2.6647    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6626   -2.4496    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.7840    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9465    1.9490   -2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0445   -0.3856    1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -1.2602    2.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3861   -1.6282    2.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901    0.8081   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656    1.6489   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870    1.3940   -0.5974 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 13  8  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
 12 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 21 34  1  0
 22 35  1  0
 23 36  1  0
M  END


  Mrv1652309102210572D          

 23 25  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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 O   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
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0915   -0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653    0.4014    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   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
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C2OC(=O)C=C2C2=CC=C(O)C(Br)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13BrO4/c1-22-13-5-2-11(3-6-13)8-17-14(10-18(21)23-17)12-4-7-16(20)15(19)9-12/h2-10,20H,1H3

> <INCHI_KEY>
RMWGZBOMTPESNY-UHFFFAOYSA-N

> <FORMULA>
C18H13BrO4

> <MOLECULAR_WEIGHT>
373.202

> <EXACT_MASS>
371.999722

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
34.69613976319753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.183374993666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.779019385308647

> <JCHEM_PKA_STRONGEST_BASIC>
-4.82341926442733

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
92.22250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.521  -3.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.986  -3.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.771  -1.312   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0      -3.482   0.749   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0      -1.697  -1.233   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
CONECT   22    6   23                                                       
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₃BrO₄

Average Mass

373.2020 Da

Monoisotopic Mass

371.99972 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C2OC(=O)C=C2C2=CC=C(O)C(Br)=C2)C=C1

InChI Identifier

InChI=1S/C18H13BrO4/c1-22-13-5-2-11(3-6-13)8-17-14(10-18(21)23-17)12-4-7-16(20)15(19)9-12/h2-10,20H,1H3

InChI Key

RMWGZBOMTPESNY-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
2-halophenol
2-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Halobenzene
Phenol
Bromobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
2-furanone
Dihydrofuran
Enol ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Organohalogen compound
Organic oxygen compound
Carbonyl group
Organobromide
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	4.18	ChemAxon
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.22 m³·mol⁻¹	ChemAxon
Polarizability	34.7 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

28650717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73345226

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sikorska J, Parker-Nance S, Davies-Coleman MT, Vining OB, Sikora AE, McPhail KL: Antimicrobial rubrolides from a South African species of Synoicum tunicate. J Nat Prod. 2012 Oct 26;75(10):1824-7. doi: 10.1021/np300580z. Epub 2012 Oct 2. [PubMed:23030848 ]
Penkler DL, Tastan Bishop O: Modulation of Human Hsp90alpha Conformational Dynamics by Allosteric Ligand Interaction at the C-Terminal Domain. Sci Rep. 2019 Feb 7;9(1):1600. doi: 10.1038/s41598-018-35835-0. [PubMed:30733455 ]
LOTUS database [Link]

Showing NP-Card for 4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one (NP0298050)

MOL for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

3D MOL for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

3D SDF for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

3D-SDF for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

PDB for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

3D PDB for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

SMILES for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

INCHI for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

Structure for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)

3D Structure for NP0298050 (4-(3-bromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one)