NP-MRD: Showing NP-Card for 1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (NP0268788)

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Record Information

Version

2.0

Created at

2022-09-08 14:01:40 UTC

Updated at

2022-09-08 14:01:41 UTC

NP-MRD ID

NP0268788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

Description

1'-Acetoxychavicol acetate, also known as galangal acetate, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. 1'-Acetoxychavicol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1'-Acetoxychavicol acetate has been detected, but not quantified in, herbs and spices. 1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate is found in Alpinia conchigera, Alpinia galanga and Piper cubeba. This could make 1'-acetoxychavicol acetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.3485   -2.6011   -1.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -1.9419   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552   -0.4586   -0.5092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6857    0.0721    0.5852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371    1.0841    0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712    1.6055    1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.4990   -0.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223   -0.3164   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698    0.8674    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2490    1.0425    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437    0.0170    0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    0.1893    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781    0.6747   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7980    0.8462    0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    0.9632   -1.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7272   -1.1932   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3689   -1.3342   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251   -2.0507   -2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518   -3.6533   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3643   -2.4864    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205    0.0058   -1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973    1.7339    2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    0.9071    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8328    2.5817    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612    1.7103    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    1.9960    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2733    1.5526   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2688   -0.1795    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407    1.1549    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952   -2.0208   -0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361   -2.2673   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  2  0
 17  8  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  3 21  1  6
  2 20  1  0
  1 18  1  0
  1 19  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv0541 05061312192D          

 17 17  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    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
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
   -4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   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
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268788

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3

> <INCHI_KEY>
JAMQIUWGGBSIKZ-UHFFFAOYSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.2479

> <EXACT_MASS>
234.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.281028661960846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.045299326666667

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7784067139381206

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
61.990700000000025

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   3.080   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   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002   3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    1   13                                                       
CONECT    5    7   11                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9    2   14   16                                                  
CONECT   10    3   15   17                                                  
CONECT   11    5    6   13                                                  
CONECT   12    7    8   16                                                  
CONECT   13    4   11   17                                                  
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16    9   12                                                       
CONECT   17   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
1'-Acetoxychavicol acetic acid	Generator
(1S)-1-[4-(Acetyloxy)phenyl]prop-2-en-1-yl acetate	HMDB
(AlphaS)-4-(acetyloxy)-alpha-ethenylbenzenemethanol	HMDB
1's-1'-Acetoxychavicol acetate	HMDB
Galangal acetate	HMDB
1-[4-(Acetyloxy)phenyl]prop-2-en-1-yl acetic acid	Generator
1's-Acetoxychavicol acetic acid	Generator

Chemical Formula

C₁₃H₁₄O₄

Average Mass

234.2479 Da

Monoisotopic Mass

234.08921 Da

IUPAC Name

1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

Traditional Name

1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C1

InChI Identifier

InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3

InChI Key

JAMQIUWGGBSIKZ-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
Alpinia conchigera	LOTUS Database	35616633
Alpinia galanga	LOTUS Database	35616633
Piper cubeba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Benzyloxycarbonyl
Phenoxy compound
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
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	2.58	ALOGPS
logP	2.05	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.99 m³·mol⁻¹	ChemAxon
Polarizability	24.28 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

HMDB0041005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020865

KNApSAcK ID

Not Available

Chemspider ID

354584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

400072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (NP0268788)

MOL for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

3D MOL for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

3D SDF for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

3D-SDF for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

PDB for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

3D PDB for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

SMILES for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

INCHI for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

Structure for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)

3D Structure for NP0268788 (1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate)