NP-MRD: Showing NP-Card for 1'-Acetoxyeugenol acetate. (NP0084680)

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Record Information

Version

2.0

Created at

2022-04-29 05:20:52 UTC

Updated at

2022-04-29 05:20:53 UTC

NP-MRD ID

NP0084680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1'-Acetoxyeugenol acetate.

Description

1'-Acetoxyeugenol 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'-Acetoxyeugenol acetate 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. 1'-Acetoxyeugenol acetate. is found in Alpinia galanga . 1'-Acetoxyeugenol acetate. was first documented in 2015 (PMID: 25464007). Based on a literature review a small amount of articles have been published on 1'-acetoxyeugenol acetate (PMID: 35204176) (PMID: 29571480) (PMID: 29075101) (PMID: 27756508).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -3.5579   -2.3628   -1.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4155   -2.1882   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0992   -0.9167    0.2961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8020    0.1651   -0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6560    0.9900    0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    2.1222   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334    0.7851    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -0.6440    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -0.2568   -1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    0.0046   -1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -0.1087   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153    0.1727   -0.9730 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8837    1.4316   -0.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2864    1.7201   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    2.3598   -0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578   -0.4995    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -0.6230    1.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406   -1.0163    2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252   -0.7617    0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095   -3.2780   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014   -1.5662   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747   -2.9724   -0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213   -1.0087    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3860    1.8280   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    2.5677   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4603    2.9355    0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594   -0.1542   -2.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3161    0.3144   -2.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5636    2.7179   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9545    0.9196   -0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925    1.7834   -2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965   -1.8613    2.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264   -1.3956    3.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -0.1336    3.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -1.0700    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8 19  2  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  2  1  0
  2  1  2  3
 19 16  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 10 28  1  0
  9 27  1  0
 19 35  1  0
  3 23  1  1
  6 24  1  0
  6 25  1  0
  6 26  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652304292207202D          

 19 19  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 19  2  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC(C)=O)C=CC(=C1)[C@@H](OC(C)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O5/c1-5-12(18-9(2)15)11-6-7-13(19-10(3)16)14(8-11)17-4/h5-8,12H,1H2,2-4H3/t12-/m0/s1

> <INCHI_KEY>
NKRBAUXTIWONOV-LBPRGKRZSA-N

> <FORMULA>
C14H16O5

> <MOLECULAR_WEIGHT>
264.277

> <EXACT_MASS>
264.099773615

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.14409106688371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
1.887628061

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.899974491038187

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
68.45390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
engenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17                                                            
CONECT   19   11    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetate	ChEBI
4-(Acetyloxy)-a-ethenyl-3-methoxybenzenemethanol acetate	Generator
4-(Acetyloxy)-a-ethenyl-3-methoxybenzenemethanol acetic acid	Generator
4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetic acid	Generator
4-(Acetyloxy)-α-ethenyl-3-methoxybenzenemethanol acetate	Generator
4-(Acetyloxy)-α-ethenyl-3-methoxybenzenemethanol acetic acid	Generator
1'-Acetoxyeugenol acetic acid	Generator
1'-Acetoxyeugenol	MeSH

Chemical Formula

C₁₄H₁₆O₅

Average Mass

264.2770 Da

Monoisotopic Mass

264.09977 Da

IUPAC Name

(1S)-1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

Traditional Name

engenol

CAS Registry Number

Not Available

SMILES

COC1=C(OC(C)=O)C=CC(=C1)[C@@H](OC(C)=O)C=C

InChI Identifier

InChI=1S/C14H16O5/c1-5-12(18-9(2)15)11-6-7-13(19-10(3)16)14(8-11)17-4/h5-8,12H,1H2,2-4H3/t12-/m0/s1

InChI Key

NKRBAUXTIWONOV-LBPRGKRZSA-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
Alpinia galanga	Plant	KNApSAcK

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

Benzyloxycarbonyl
Phenol ester
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:470 )
acetate ester (CHEBI:470 )
monomethoxybenzene (CHEBI:470 )

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	2.27	ALOGPS
logP	1.89	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.45 m³·mol⁻¹	ChemAxon
Polarizability	27.14 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054209

Chemspider ID

391114

KEGG Compound ID

C10427

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442775

PDB ID

Not Available

ChEBI ID

470

Good Scents ID

rw1435021

References

General References

Choi JY, Lee NK, Wang YY, Hong JP, Son SR, Gu DH, Jang DS, Choi JH: 1'-Acetoxyeugenol Acetate Isolated from Thai Ginger Induces Apoptosis in Human Ovarian Cancer Cells by ROS Production via NADPH Oxidase. Antioxidants (Basel). 2022 Jan 31;11(2). pii: antiox11020293. doi: 10.3390/antiox11020293. [PubMed:35204176 ]
Tang X, Xu C, Yagiz Y, Simonne A, Marshall MR: Phytochemical profiles, and antimicrobial and antioxidant activities of greater galangal [Alpinia galanga (Linn.) Swartz.] flowers. Food Chem. 2018 Jul 30;255:300-308. doi: 10.1016/j.foodchem.2018.02.027. Epub 2018 Feb 7. [PubMed:29571480 ]
Liew SK, Azmi MN, In L, Awang K, Nagoor NH: Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1'S-1'-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells. Drug Des Devel Ther. 2017 Sep 18;11:2763-2776. doi: 10.2147/DDDT.S130349. eCollection 2017. [PubMed:29075101 ]
Manse Y, Ninomiya K, Nishi R, Kamei I, Katsuyama Y, Imagawa T, Chaipech S, Muraoka O, Morikawa T: Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit. Bioorg Med Chem. 2016 Dec 1;24(23):6215-6224. doi: 10.1016/j.bmc.2016.10.001. Epub 2016 Oct 6. [PubMed:27756508 ]
Zeng QH, Lu CL, Zhang XW, Jiang JG: Isolation and identification of ingredients inducing cancer cell death from the seeds of Alpinia galanga, a Chinese spice. Food Funct. 2015 Feb;6(2):431-43. doi: 10.1039/c4fo00709c. [PubMed:25464007 ]

Showing NP-Card for 1'-Acetoxyeugenol acetate. (NP0084680)

MOL for NP0084680 (1'-Acetoxyeugenol acetate.)

3D MOL for NP0084680 (1'-Acetoxyeugenol acetate.)

3D SDF for NP0084680 (1'-Acetoxyeugenol acetate.)

3D-SDF for NP0084680 (1'-Acetoxyeugenol acetate.)

PDB for NP0084680 (1'-Acetoxyeugenol acetate.)

3D PDB for NP0084680 (1'-Acetoxyeugenol acetate.)

SMILES for NP0084680 (1'-Acetoxyeugenol acetate.)

INCHI for NP0084680 (1'-Acetoxyeugenol acetate.)

Structure for NP0084680 (1'-Acetoxyeugenol acetate.)

3D Structure for NP0084680 (1'-Acetoxyeugenol acetate.)