NP-MRD: Showing NP-Card for (3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (NP0321655)

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Record Information

Version

2.0

Created at

2022-09-11 23:58:32 UTC

Updated at

2022-09-11 23:58:32 UTC

NP-MRD ID

NP0321655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one

Description

CHEMBL240090 belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. (3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one is found in Polysiphonia urceolata and Rhodomela confervoides. Based on a literature review very few articles have been published on CHEMBL240090.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122201582D          

 14 14  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    2.1434   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321655

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H9BrO3/c1-6(12)2-3-7-4-8(11)10(14)9(13)5-7/h2-5,13-14H,1H3/b3-2+

> <INCHI_KEY>
MYKFZEDOPLREOR-NSCUHMNNSA-N

> <FORMULA>
C10H9BrO3

> <MOLECULAR_WEIGHT>
257.083

> <EXACT_MASS>
255.973507

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
21.844121552964168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one

> <JCHEM_LOGP>
2.627333764666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.73178607849449

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8337714639581435

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8365532146543515

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
58.1956

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₉BrO₃

Average Mass

257.0830 Da

Monoisotopic Mass

255.97351 Da

IUPAC Name

(3E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one

Traditional Name

(3E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C\C1=CC(O)=C(O)C(Br)=C1

InChI Identifier

InChI=1S/C10H9BrO3/c1-6(12)2-3-7-4-8(11)10(14)9(13)5-7/h2-5,13-14H,1H3/b3-2+

InChI Key

MYKFZEDOPLREOR-NSCUHMNNSA-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
Polysiphonia urceolata	LOTUS Database	35616633
Rhodomela confervoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Catechol
3-halophenol
2-halophenol
3-bromophenol
2-bromophenol
Styrene
Bromobenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Organic oxygen compound
Organobromide
Carbonyl group
Organooxygen compound
Organohalogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.63	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.2 m³·mol⁻¹	ChemAxon
Polarizability	21.84 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

23076591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44437164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (NP0321655)

MOL for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

3D MOL for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

3D SDF for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

3D-SDF for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

PDB for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

3D PDB for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

SMILES for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

INCHI for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

Structure for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)

3D Structure for NP0321655 ((3e)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one)