NP-MRD: Showing NP-Card for [3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate (NP0160721)

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Record Information

Version

2.0

Created at

2022-09-02 18:43:58 UTC

Updated at

2022-09-02 18:43:58 UTC

NP-MRD ID

NP0160721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate

Description

Piperenol A triacetate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Piperenol A triacetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Piperenol A triacetate has been detected, but not quantified in, herbs and spices. [3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate is found in Piper cubeba. This could make piperenol a triacetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312442D          

 37 39  0  0  0  0            999 V2000
   -5.7158   -1.6500    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
   -6.4302    1.2375    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
   -4.2868    4.9500    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
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
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  6  4  2  0  0  0  0
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 37 27  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061312442D          

 37 39  0  0  0  0            999 V2000
   -5.7158   -1.6500    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
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M  END
> <DATABASE_ID>
NP0160721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C=C(COC(=O)C2=CC=CC=C2)C(OC(C)=O)C(OC(=O)C2=CC=CC=C2)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O10/c1-16(28)34-22-14-21(15-33-26(31)19-10-6-4-7-11-19)23(35-17(2)29)25(24(22)36-18(3)30)37-27(32)20-12-8-5-9-13-20/h4-14,22-25H,15H2,1-3H3

> <INCHI_KEY>
UGMVPWAZGUPKPL-UHFFFAOYSA-N

> <FORMULA>
C27H26O10

> <MOLECULAR_WEIGHT>
510.4893

> <EXACT_MASS>
510.152597052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
50.79265922518681

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.282441948666666

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.270287949770788

> <JCHEM_POLAR_SURFACE_AREA>
131.5

> <JCHEM_REFRACTIVITY>
127.32379999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate

> <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     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -10.669   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4    6    7                                                       
CONECT    5    8    9                                                       
CONECT    6    4   10                                                       
CONECT    7    4   11                                                       
CONECT    8    5   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   19                                                       
CONECT   11    7   19                                                       
CONECT   12    8   20                                                       
CONECT   13    9   20                                                       
CONECT   14   21   22                                                       
CONECT   15   21   33                                                       
CONECT   16    1   28   34                                                  
CONECT   17    2   29   35                                                  
CONECT   18    3   30   36                                                  
CONECT   19   10   11   26                                                  
CONECT   20   12   13   27                                                  
CONECT   21   14   15   23                                                  
CONECT   22   14   24   34                                                  
CONECT   23   21   25   35                                                  
CONECT   24   22   25   36                                                  
CONECT   25   23   24   37                                                  
CONECT   26   19   31   33                                                  
CONECT   27   20   32   37                                                  
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   26                                                            
CONECT   32   27                                                            
CONECT   33   15   26                                                       
CONECT   34   16   22                                                       
CONECT   35   17   23                                                       
CONECT   36   18   24                                                       
CONECT   37   25   27                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
Piperenol a triacetic acid	Generator
[3,4,6-Tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoic acid	Generator

Chemical Formula

C₂₇H₂₆O₁₀

Average Mass

510.4893 Da

Monoisotopic Mass

510.15260 Da

IUPAC Name

[3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate

Traditional Name

[3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C=C(COC(=O)C2=CC=CC=C2)C(OC(C)=O)C(OC(=O)C2=CC=CC=C2)C1OC(C)=O

InChI Identifier

InChI=1S/C27H26O10/c1-16(28)34-22-14-21(15-33-26(31)19-10-6-4-7-11-19)23(35-17(2)29)25(24(22)36-18(3)30)37-27(32)20-12-8-5-9-13-20/h4-14,22-25H,15H2,1-3H3

InChI Key

UGMVPWAZGUPKPL-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
Piper cubeba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Cyclitol or derivatives
Carboxylic acid ester
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	3.17	ALOGPS
logP	3.28	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	127.32 m³·mol⁻¹	ChemAxon
Polarizability	50.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041535

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021515

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

14890279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate (NP0160721)

MOL for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

3D MOL for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

3D SDF for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

3D-SDF for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

PDB for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

3D PDB for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

SMILES for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

INCHI for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

Structure for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)

3D Structure for NP0160721 ([3,4,6-tris(acetyloxy)-5-(benzoyloxy)cyclohex-1-en-1-yl]methyl benzoate)