NP-MRD: Showing NP-Card for Ethyl 3-(N-butylacetamido)propionate (NP0083981)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:51:32 UTC

Updated at

2022-04-29 04:51:32 UTC

NP-MRD ID

NP0083981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl 3-(N-butylacetamido)propionate

Description

52304-36-6, Also known as repellent 3535 or EBAAP, belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H). Ethyl 3-(N-butylacetamido)propionate is found in Averrhoa bilimbi . 52304-36-6 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.2918    1.7704   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3169    0.5336    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1203   -0.3415   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260    0.3330    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -0.6387    0.1126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0227   -0.7158   -1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318    0.2180   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.3653   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074   -0.2134    0.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    1.2372   -1.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931    1.4240   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824    0.1519   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4191   -1.4163    1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635   -2.5079    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291   -1.1759    2.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153    2.4207   -0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456    1.5629   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1844    2.3861   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421    0.7928    1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2030   -0.0691   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -0.7404   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2700   -1.2331    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    1.1665   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795    0.6901    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3268   -1.7810   -1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -0.6556   -1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    1.2556   -1.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -0.0931   -2.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    1.9670    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0647    2.1021   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1973    0.4512    0.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2434   -0.3636   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -0.4918    0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1274   -2.6079    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -2.3337    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -3.4498    1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv1572004221603592D          

 15 14  0  0  0  0            999 V2000
    3.8230   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCN(CCC(=O)OCC)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3

> <INCHI_KEY>
VZRKEAFHFMSHCD-UHFFFAOYSA-N

> <FORMULA>
C11H21NO3

> <MOLECULAR_WEIGHT>
215.293

> <EXACT_MASS>
215.15214354

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.468422075117715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-(N-butylacetamido)propanoate

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.9586608733333335

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.291331618833405

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
58.43460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-(N-butylacetamido)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       7.136  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.473  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.805  -0.921   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.139  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.138  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.137  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.805  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.471  -1.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.472  -4.001   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.471  -3.231   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      11.137  -0.921   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      16.472  -5.541   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      17.806  -3.231   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   10                                                            
CONECT    4    1    6                                                       
CONECT    5    2   15                                                       
CONECT    6    4    8                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   12                                                       
CONECT   10    3   12   13                                                  
CONECT   11    7   14   15                                                  
CONECT   12    8    9   10                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    5   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Ethyl butylacetylaminopropionate	Kegg
Ethyl butylacetylaminopropionic acid	Generator
3-(N-N-Butyl)-N-acetylaminopropionic acid ethyl ester	MeSH
Ethyl-3-(N-N-butyl-N-acetyl)aminopropionate	MeSH
Insect repellent m 3535	MeSH
Repellent 3535	MeSH
EBAAP	MeSH
Insect repellent merck 3535	MeSH
Ethyl 3-[acetyl(butyl)amino]propanoic acid	Generator
Ethyl 3-(N-butylacetamido)propanoic acid	Generator

Chemical Formula

C₁₁H₂₁NO₃

Average Mass

215.2930 Da

Monoisotopic Mass

215.15214 Da

IUPAC Name

ethyl 3-(N-butylacetamido)propanoate

Traditional Name

ethyl 3-(N-butylacetamido)propanoate

CAS Registry Number

Not Available

SMILES

CCCCN(CCC(=O)OCC)C(C)=O

InChI Identifier

InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3

InChI Key

VZRKEAFHFMSHCD-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
Averrhoa bilimbi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Tertiary carboxylic acid amides

Alternative Parents

Substituents

Acetamide
Tertiary carboxylic acid amide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxamide (CHEBI:81991 )
Insect repellents (C18830 )

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	1.68	ALOGPS
logP	0.96	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	58.43 m³·mol⁻¹	ChemAxon
Polarizability	24.47 Å³	ChemAxon
Number of Rings	0	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

C18830

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ethyl 3-(N-butylacetamido)propionate (NP0083981)

MOL for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

3D MOL for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

3D SDF for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

3D-SDF for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

PDB for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

3D PDB for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

SMILES for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

INCHI for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

Structure for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)

3D Structure for NP0083981 (Ethyl 3-(N-butylacetamido)propionate)