NP-MRD: Showing NP-Card for isobutyl cinnamate (NP0290583)

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Record Information

Version

2.0

Created at

2022-09-09 21:20:08 UTC

Updated at

2022-09-09 21:20:09 UTC

NP-MRD ID

NP0290583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isobutyl cinnamate

Description

Isobutyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. isobutyl cinnamate is found in Artemisia salsoloides. isobutyl cinnamate was first documented in 2007 (PMID: 18036714). Based on a literature review a small amount of articles have been published on Isobutyl cinnamate (PMID: 35024988) (PMID: 34363880) (PMID: 25809993).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    3.2283   -0.3587    1.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -0.8518    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -0.7739    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023    0.0206   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060    0.0600   -0.3610 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6443    0.8344   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452    1.4747   -2.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8276    0.9067   -1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    0.2121   -0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003    0.2059    0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -0.5598    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6750   -0.6028    1.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5286    0.1310    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0288    0.8889   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    0.9287   -0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -1.0948    2.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939    0.6437    2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1407   -0.3139    2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.9060    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2780   -1.6696   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -0.7903    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310    0.1015   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664    1.0263   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0050   -0.4001   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214    1.5010   -1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7292   -0.3913    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689   -1.1541    1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0838   -1.1923    2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6147    0.1176    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7173    1.4567   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3587    1.5497   -1.5052 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv1652309092223202D          

 15 15  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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    5.7158   -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
    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  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 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290583

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O2/c1-11(2)10-15-13(14)9-8-12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3/b9-8+

> <INCHI_KEY>
IQZUZPKOFSOVET-CMDGGOBGSA-N

> <FORMULA>
C13H16O2

> <MOLECULAR_WEIGHT>
204.269

> <EXACT_MASS>
204.115029755

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.5573695977154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methylpropyl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
3.759616825333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.809451972007504

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
61.573200000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-methylpropyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+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  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   15  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                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Isobutyl cinnamic acid	Generator

Chemical Formula

C₁₃H₁₆O₂

Average Mass

204.2690 Da

Monoisotopic Mass

204.11503 Da

IUPAC Name

2-methylpropyl (2E)-3-phenylprop-2-enoate

Traditional Name

2-methylpropyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H16O2/c1-11(2)10-15-13(14)9-8-12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3/b9-8+

InChI Key

IQZUZPKOFSOVET-CMDGGOBGSA-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
Artemisia salsoloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	3.76	ChemAxon
pKa (Strongest Basic)	-6.8	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	61.57 m³·mol⁻¹	ChemAxon
Polarizability	23.56 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

680686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

778574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kang MS, Park JH, Lee HS: Acaricidal potential of active components derived from Alpinia galanga rhizome oils and their derivatives against Haemaphysalis longicornis (Acari: Ixodidae). Exp Appl Acarol. 2022 Feb;86(2):313-326. doi: 10.1007/s10493-022-00685-z. Epub 2022 Jan 13. [PubMed:35024988 ]
Api AM, Belsito D, Botelho D, Bruze M, Burton GA Jr, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Jones L, Joshi K, Kumar M, Lapczynski A, Lavelle M, Lee I, Liebler DC, Moustakas H, Na M, Penning TM, Ritacco G, Romine J, Sadekar N, Schultz TW, Selechnik D, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y: RIFM fragrance ingredient safety assessment, isobutyl cinnamate, CAS Registry Number 122-67-8. Food Chem Toxicol. 2021 Oct;156 Suppl 1:112456. doi: 10.1016/j.fct.2021.112456. Epub 2021 Aug 4. [PubMed:34363880 ]
Kim JH, Bhatia SK, Yoo D, Seo HM, Yi DH, Kim HJ, Lee JH, Choi KY, Kim KJ, Lee YK, Yang YH: Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters. Appl Biochem Biotechnol. 2015 May;176(1):244-52. doi: 10.1007/s12010-015-1570-x. Epub 2015 Mar 27. [PubMed:25809993 ]
Bhatia SP, Wellington GA, Cocchiara J, Lalko J, Letizia CS, Api AM: Fragrance material review on isobutyl cinnamate. Food Chem Toxicol. 2007;45 Suppl 1:S102-5. doi: 10.1016/j.fct.2007.09.078. Epub 2007 Sep 15. [PubMed:18036714 ]
LOTUS database [Link]

Showing NP-Card for isobutyl cinnamate (NP0290583)

MOL for NP0290583 (isobutyl cinnamate)

3D MOL for NP0290583 (isobutyl cinnamate)

3D SDF for NP0290583 (isobutyl cinnamate)

3D-SDF for NP0290583 (isobutyl cinnamate)

PDB for NP0290583 (isobutyl cinnamate)

3D PDB for NP0290583 (isobutyl cinnamate)

SMILES for NP0290583 (isobutyl cinnamate)

INCHI for NP0290583 (isobutyl cinnamate)

Structure for NP0290583 (isobutyl cinnamate)

3D Structure for NP0290583 (isobutyl cinnamate)