NP-MRD: Showing NP-Card for Benzyl 2,3-dimethyl-2-butenoate (NP0337803)

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Record Information

Version

2.0

Created at

2024-09-11 12:32:38 UTC

Updated at

2024-09-11 12:32:38 UTC

NP-MRD ID

NP0337803

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzyl 2,3-dimethyl-2-butenoate

Description

Benzyl 2,3-dimethyl-2-butenoate, also known as benzyl 2,3-dimethylcrotonate or benzyl methyltiglate, belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl 2,3-dimethyl-2-butenoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzyl 2,3-dimethyl-2-butenoate is a fruity, herbal, and spicy tasting compound. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308572D          

 15 15  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    1.4289    0.0000    0.0000 C   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
    1.4289    0.8250    0.0000 C   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337803

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C(C)C(=O)OCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O2/c1-10(2)11(3)13(14)15-9-12-7-5-4-6-8-12/h4-8H,9H2,1-3H3

> <INCHI_KEY>
LHDWSNQMWAZQPX-UHFFFAOYSA-N

> <FORMULA>
C13H16O2

> <MOLECULAR_WEIGHT>
204.2649

> <EXACT_MASS>
204.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.368137473818052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl 2,3-dimethylbut-2-enoate

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.662194555000001

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.862972704990316

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.98570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl 2,3-dimethylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9   12   15                                                       
CONECT   10    1    2   11                                                  
CONECT   11    3   10   13                                                  
CONECT   12    7    8    9                                                  
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Benzyl 2,3-dimethyl-2-butenoic acid	Generator
2-Butenoic acid, 2,3-dimethyl-, phenylmethyl ester	HMDB
Benzyl 2,3-dimethylcrotonate	HMDB
Benzyl methyltiglate	HMDB
Crotonic acid, 2,3-dimethyl-, benzyl ester	HMDB
FEMA 2143	HMDB
Phenylmethyl 2,3-dimethyl-2-butenoate	HMDB
Benzyl 2,3-dimethylbut-2-enoic acid	Generator

Chemical Formula

C₁₃H₁₆O₂

Average Mass

204.2649 Da

Monoisotopic Mass

204.11503 Da

IUPAC Name

benzyl 2,3-dimethylbut-2-enoate

Traditional Name

benzyl 2,3-dimethylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=C(C)C(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C13H16O2/c1-10(2)11(3)13(14)15-9-12-7-5-4-6-8-12/h4-8H,9H2,1-3H3

InChI Key

LHDWSNQMWAZQPX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.71	ALOGPS
logP	3.66	ChemAxon
logS	-3.2	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	4	ChemAxon
Refractivity	60.99 m³·mol⁻¹	ChemAxon
Polarizability	23.37 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

HMDB ID

HMDB0036224

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015082

KNApSAcK ID

Not Available

Chemspider ID

55331

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Benzyl 2,3-dimethyl-2-butenoate (NP0337803)

MOL for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

3D MOL for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

3D SDF for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

3D-SDF for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

PDB for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

3D PDB for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

SMILES for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

INCHI for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

Structure for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)

3D Structure for NP0337803 (Benzyl 2,3-dimethyl-2-butenoate)