NP-MRD: Showing NP-Card for Butyl phenylacetate (NP0006797)

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Record Information

Version

2.0

Created at

2020-12-09 03:43:49 UTC

Updated at

2021-08-19 23:59:43 UTC

NP-MRD ID

NP0006797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butyl phenylacetate

Provided By

NPAtlas

Description

Butyl benzoate, also known as anthrapole az or dai cari XBN, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Butyl benzoate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Butyl phenylacetate is found in Carica pubescens, Hamamelis virginiana, Spondias mombin and Streptomyces. Butyl phenylacetate was first documented in 2003 (PMID: 12799010). Based on a literature review a small amount of articles have been published on Butyl benzoate (PMID: 26852620).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 27 27  0  0  0  0            999 V2000
   -4.1943   -0.4108    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -0.3383   -0.5767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6045    0.3549   -0.8353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5460   -0.4838   -0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2542    0.0638   -0.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.5876    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -1.6424    0.8975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807   -0.0920    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2252   -0.7750    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -0.3491    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193    0.7980   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    1.5096   -0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    1.0484   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808    0.5261    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2924   -0.6096    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -1.2548    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8595   -1.3839   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    0.1690   -1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991    0.4089   -1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.3464   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543   -0.5535    0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -1.5347   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0188   -1.6866    1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3551   -0.8851    1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549    1.1473   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860    2.4167   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.5876   -1.0331 H   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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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  8  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  9 23  1  0  0  0  0
 10 24  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END


  Mrv1652306242118353D          

 27 27  0  0  0  0            999 V2000
   -4.1943   -0.4108    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -0.3383   -0.5767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6045    0.3549   -0.8353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5460   -0.4838   -0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2542    0.0638   -0.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.5876    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -1.6424    0.8975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807   -0.0920    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2252   -0.7750    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -0.3491    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193    0.7980   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    1.5096   -0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    1.0484   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808    0.5261    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2924   -0.6096    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -1.2548    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8595   -1.3839   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    0.1690   -1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991    0.4089   -1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.3464   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543   -0.5535    0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -1.5347   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0188   -1.6866    1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3551   -0.8851    1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549    1.1473   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860    2.4167   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.5876   -1.0331 H   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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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  8  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  9 23  1  0  0  0  0
 10 24  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)OC([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O2/c1-2-3-9-13-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3

> <INCHI_KEY>
XSIFPSYPOVKYCO-UHFFFAOYSA-N

> <FORMULA>
C11H14O2

> <MOLECULAR_WEIGHT>
178.2277

> <EXACT_MASS>
178.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.426118361937576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
butyl benzoate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.300621794666667

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.890653175659674

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
51.95690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl benzoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.194  -0.411   0.900  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.944  -0.338  -0.577  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.604   0.355  -0.835  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.546  -0.484  -0.148  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.254   0.064  -0.319  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.816  -0.588   0.250  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.598  -1.642   0.898  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.181  -0.092   0.122  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.225  -0.775   0.707  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.536  -0.349   0.616  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.819   0.798  -0.082  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.793   1.510  -0.683  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.479   1.048  -0.570  0.00  0.00           C+0
HETATM   14  H   UNK     0      -3.881   0.526   1.401  0.00  0.00           H+0
HETATM   15  H   UNK     0      -5.292  -0.610   1.058  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.629  -1.255   1.326  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.860  -1.384  -0.955  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.744   0.169  -1.133  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.399   0.409  -1.918  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.627   1.346  -0.349  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.754  -0.554   0.932  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.582  -1.535  -0.546  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.019  -1.687   1.264  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.355  -0.885   1.076  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.855   1.147  -0.162  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.986   2.417  -1.240  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.649   1.588  -1.033  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3   17   18                                             
CONECT    3    2    4   19   20                                             
CONECT    4    3    5   21   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12    8   27                                                  
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    2                                                            
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    4                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Anthrapole az	ChEBI
Benzoic acid butyl ester	ChEBI
Benzoic acid N-butyl ester	ChEBI
Benzoic acid, butyl ester	ChEBI
Dai cari XBN	ChEBI
N-Butyl benzoate	ChEBI
Benzoate butyl ester	Generator
Benzoate N-butyl ester	Generator
Benzoate, butyl ester	Generator
N-Butyl benzoic acid	Generator
Butyl benzoic acid	Generator

Chemical Formula

C₁₁H₁₄O₂

Average Mass

178.2277 Da

Monoisotopic Mass

178.09938 Da

IUPAC Name

butyl benzoate

Traditional Name

butyl benzoate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H14O2/c1-2-3-9-13-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3

InChI Key

XSIFPSYPOVKYCO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Carica pubescens	Plant	KNApSAcK
Dittrichia graveolens	KNApSAcK Database	22123792
Hamamelis virginiana	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Streptomyces	NPAtlas	17193176

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	-22.00 to -21.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	127.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	59 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	3.840	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.4	ALOGPS
logP	3.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.96 m³·mol⁻¹	ChemAxon
Polarizability	20.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004519

HMDB ID

HMDB0303178

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008741

KNApSAcK ID

C00055629

Chemspider ID

8374

KEGG Compound ID

Not Available

BioCyc ID

CPD-19955

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8698

PDB ID

Not Available

ChEBI ID

156070

Good Scents ID

rw1013151

References

General References

Uchida H, Kurakata Y, Sawamura H, Inamura N, Kotani T, Uwajima T: Purification and properties of an esterase from Aspergillus nomius HS-1 degrading ethylene glycol dibenzoate. FEMS Microbiol Lett. 2003 Jun 6;223(1):123-7. doi: 10.1016/S0378-1097(03)00353-7. [PubMed:12799010 ]
Ai Y, Wu M, Li L, Zhao F, Zeng B: Highly selective and effective solid phase microextraction of benzoic acid esters using ionic liquid functionalized multiwalled carbon nanotubes-doped polyaniline coating. J Chromatogr A. 2016 Mar 11;1437:1-7. doi: 10.1016/j.chroma.2016.01.072. Epub 2016 Feb 2. [PubMed:26852620 ]

Showing NP-Card for Butyl phenylacetate (NP0006797)

MOL for NP0006797 (Butyl phenylacetate)

3D MOL for NP0006797 (Butyl phenylacetate)

3D SDF for NP0006797 (Butyl phenylacetate)

3D-SDF for NP0006797 (Butyl phenylacetate)

PDB for NP0006797 (Butyl phenylacetate)

3D PDB for NP0006797 (Butyl phenylacetate)

SMILES for NP0006797 (Butyl phenylacetate)

INCHI for NP0006797 (Butyl phenylacetate)

Structure for NP0006797 (Butyl phenylacetate)

3D Structure for NP0006797 (Butyl phenylacetate)