NP-MRD: Showing NP-Card for (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) (NP0049298)

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Record Information

Version

2.0

Created at

2022-03-17 21:10:15 UTC

Updated at

2022-03-17 21:10:15 UTC

NP-MRD ID

NP0049298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate)

Description

(5A,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) has been detected, but not quantified in, a few different foods, such as coffee and coffee products, green vegetables, and herbs and spices. (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) is found in Cichorium intybus. This could make (5a,6a,8a,11a)-8-hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310492D          

 30 33  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453   -2.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -4.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 13  3  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 12  1  0  0  0  0
 24 10  2  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 18  2  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END


  Mrv0541 05061310492D          

 30 33  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453   -2.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -4.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 13  3  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 12  1  0  0  0  0
 24 10  2  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 18  2  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(OC1=O)C1C(C=O)=CC(=O)C1=C(C)CC2OC(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9-10,12,17,20-22,25H,7-8H2,1-2H3

> <INCHI_KEY>
CICWEHOIACOOIN-UHFFFAOYSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.4166

> <EXACT_MASS>
410.136553058

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.314123302440564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.126351587666667

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.747070324287687

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.471326515916699

> <JCHEM_PKA_STRONGEST_BASIC>
-5.95855650683695

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
106.93309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-formyl-3,6-dimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)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       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.271  -5.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.366  -4.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.042  -6.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.596  -6.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.703  -2.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.347   6.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.933  -4.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.888   4.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.392  -7.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.907  -1.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.325   7.220   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.621  -8.936   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.726   1.792   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.341  -2.448   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.651   4.588   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    5   13                                                       
CONECT    4    6   13                                                       
CONECT    5    3   15                                                       
CONECT    6    4   15                                                       
CONECT    7   11   17                                                       
CONECT    8   13   18                                                       
CONECT    9   14   16                                                       
CONECT   10   14   24                                                       
CONECT   11    1    7   19                                                  
CONECT   12    2   20   23                                                  
CONECT   13    3    4    8                                                  
CONECT   14    9   10   21                                                  
CONECT   15    5    6   25                                                  
CONECT   16    9   19   26                                                  
CONECT   17    7   20   29                                                  
CONECT   18    8   27   29                                                  
CONECT   19   11   16   21                                                  
CONECT   20   12   17   22                                                  
CONECT   21   14   19   22                                                  
CONECT   22   20   21   30                                                  
CONECT   23   12   28   30                                                  
CONECT   24   10                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   18                                                            
CONECT   28   23                                                            
CONECT   29   17   18                                                       
CONECT   30   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetic acid)	Generator
9-Formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4166 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

9-formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Traditional Name

9-formyl-3,6-dimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

CAS Registry Number

374536-44-4

SMILES

CC1C2C(OC1=O)C1C(C=O)=CC(=O)C1=C(C)CC2OC(=O)CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9-10,12,17,20-22,25H,7-8H2,1-2H3

InChI Key

CICWEHOIACOOIN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cichorium intybus	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.38	ALOGPS
logP	2.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.93 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	4	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

HMDB0039048

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018545

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752526

PDB ID

Not Available

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Showing NP-Card for (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) (NP0049298)

MOL for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

3D MOL for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

3D SDF for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

3D-SDF for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

PDB for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

3D PDB for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

SMILES for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

INCHI for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

Structure for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))

3D Structure for NP0049298 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))