NP-MRD: Showing NP-Card for 2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate (NP0231707)

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Record Information

Version

2.0

Created at

2022-09-06 12:41:12 UTC

Updated at

2022-09-06 12:41:12 UTC

NP-MRD ID

NP0231707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate

Description

4-Bromophenacyl isobutanoate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate is found in Ipomoea capillacea. 4-Bromophenacyl isobutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.2202   -0.8118    0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5181    0.5005    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567    1.1077   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802    0.1844   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    0.4914   -1.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.4439    0.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827   -0.7727    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    0.3953    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960    1.5572    0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    0.1613    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    1.2227   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5600    1.0042   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -0.2614   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9717   -0.5127   -0.7147 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2571   -1.3144   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -1.0962    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3153   -0.6820    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -1.2465    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9569   -1.4978   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887    1.1905    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4151    0.3372   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1466    1.5523   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516    1.8743   -1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580   -1.2491    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242   -1.4876   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    2.2316   -0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    1.8505   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909   -2.3199   -0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2934   -1.9650    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1533004161507172D          

 16 16  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231707

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H13BrO3/c1-8(2)12(15)16-7-11(14)9-3-5-10(13)6-4-9/h3-6,8H,7H2,1-2H3

> <INCHI_KEY>
BDBPDPLJFCWUSK-UHFFFAOYSA-N

> <FORMULA>
C12H13BrO3

> <MOLECULAR_WEIGHT>
285.137

> <EXACT_MASS>
284.004807

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.627284486350142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.167045449666667

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.681820024134684

> <JCHEM_PKA_STRONGEST_BASIC>
-7.027747925653357

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
64.13870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0      14.670 -10.010   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
4-Bromophenacyl isobutanoic acid	Generator

Chemical Formula

C₁₂H₁₃BrO₃

Average Mass

285.1370 Da

Monoisotopic Mass

284.00481 Da

IUPAC Name

2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate

Traditional Name

2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H13BrO3/c1-8(2)12(15)16-7-11(14)9-3-5-10(13)6-4-9/h3-6,8H,7H2,1-2H3

InChI Key

BDBPDPLJFCWUSK-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
Ipomoea capillacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Alpha-acyloxy ketone
Halobenzene
Bromobenzene
Aryl bromide
Benzenoid
Monocyclic benzene moiety
Aryl halide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
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	2.82	ALOGPS
logP	3.17	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.14 m³·mol⁻¹	ChemAxon
Polarizability	25.63 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

603110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate (NP0231707)

MOL for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

3D MOL for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

3D SDF for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

3D-SDF for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

PDB for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

3D PDB for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

SMILES for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

INCHI for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

Structure for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)

3D Structure for NP0231707 (2-(4-bromophenyl)-2-oxoethyl 2-methylpropanoate)