NP-MRD: Showing NP-Card for Physalin H (NP0137009)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:53 UTC

Updated at

2022-05-30 16:38:53 UTC

NP-MRD ID

NP0137009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Physalin H

Description

2-Phenylethyl acetate, also known as 2-phenethyl acetic acid or benzylcarbinyl acetate, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phenylethyl acetate is a sweet, floral, and fruity tasting compound. Outside of the human body, 2-Phenylethyl acetate is found, on average, in the highest concentration within ceylon cinnamons and cloves. 2-Phenylethyl acetate has also been detected, but not quantified in, several different foods, such as purple mangosteens, jujubes, common pea, cocoa beans, and agaves. This could make 2-phenylethyl acetate a potential biomarker for the consumption of these foods. Physalin H is found in Alkekengi officinarum. Physalin H was first documented in 2015 (PMID: 25664918). The acetate ester of 2-phenylethanol (PMID: 25886016).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307342D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061307342D          

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 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 22  1  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 18  1  0  0  0  0
 23  2  1  0  0  0  0
 23 12  1  0  0  0  0
 23 15  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  7  1  0  0  0  0
 25 16  1  0  0  0  0
 25 23  1  0  0  0  0
 26  8  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29 25  1  0  0  0  0
 30 15  2  0  0  0  0
 31 16  1  0  0  0  0
 32 19  2  0  0  0  0
 33 20  2  0  0  0  0
 34 21  2  0  0  0  0
 35 26  1  0  0  0  0
 36 11  1  0  0  0  0
 36 27  1  0  0  0  0
 37 17  1  0  0  0  0
 37 20  1  0  0  0  0
 38 21  1  0  0  0  0
 38 24  1  0  0  0  0
 39 27  1  0  0  0  0
 39 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)C3(O)CCC4C(CC(O)C5(Cl)CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H31ClO10/c1-22-10-17-24(3)28-18(22)19(32)27(39-28,36-11-14(22)20(33)37-17)13-9-16(31)25(29)7-4-5-15(30)23(25,2)12(13)6-8-26(28,35)21(34)38-24/h4-5,12-14,16-18,31,35H,6-11H2,1-3H3

> <INCHI_KEY>
YNEPXUIPALKHAU-UHFFFAOYSA-N

> <FORMULA>
C28H31ClO10

> <MOLECULAR_WEIGHT>
562.993

> <EXACT_MASS>
562.160574919

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53374700616345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-chloro-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
2.1108884580000002

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.528133629464753

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.676499409904956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.294984095219016

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
130.79219999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-chloro-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone

> <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       2.055   1.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.567  -1.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.042  -3.582   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.222   0.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.623  -1.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.447  -2.023   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.292   1.302   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.237  -2.974   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.307   2.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.037  -0.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.714   2.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.637  -0.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.708   0.729   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.463   1.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.095  -1.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.835   2.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.482  -1.944   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.176  -0.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.982  -0.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.141   1.053   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.974  -4.279   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.969   0.211   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.166  -0.307   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.142  -2.598   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.764   1.111   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.685  -2.858   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.110   1.014   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.668  -1.676   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0       9.363   2.530   0.000  0.00  0.00          Cl+0
HETATM   30  O   UNK     0       8.497  -2.954   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.434   3.758   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.069  -1.504   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.239   2.134   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.711  -5.631   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.445  -4.197   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.330   2.480   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.610  -0.584   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.447  -4.113   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.771   0.337   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5    7                                                       
CONECT    5    4   15                                                       
CONECT    6    8   12                                                       
CONECT    7    4   25                                                       
CONECT    8    6   26                                                       
CONECT    9   13   16                                                       
CONECT   10   17   22                                                       
CONECT   11   14   36                                                       
CONECT   12    6   13   23                                                  
CONECT   13    9   12   27                                                  
CONECT   14   11   20   22                                                  
CONECT   15    5   23   30                                                  
CONECT   16    9   25   31                                                  
CONECT   17   10   24   37                                                  
CONECT   18   19   22   28                                                  
CONECT   19   18   27   32                                                  
CONECT   20   14   33   37                                                  
CONECT   21   26   34   38                                                  
CONECT   22    1   10   14   18                                             
CONECT   23    2   12   15   25                                             
CONECT   24    3   17   28   38                                             
CONECT   25    7   16   23   29                                             
CONECT   26    8   21   28   35                                             
CONECT   27   13   19   36   39                                             
CONECT   28   18   24   26   39                                             
CONECT   29   25                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   26                                                            
CONECT   36   11   27                                                       
CONECT   37   17   20                                                       
CONECT   38   21   24                                                       
CONECT   39   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   92    0
END

View in JSmol

Synonyms

Value	Source
2-Phenethyl acetate	ChEBI
Acetic acid beta-phenylethyl ester	ChEBI
Acetic acid, 2-phenylethyl ester	ChEBI
Acetic acid, phenethyl ester	ChEBI
Benzylcarbinyl acetate	ChEBI
beta-Phenethyl acetate	ChEBI
beta-Phenylethyl acetate	ChEBI
Phenethyl alcohol, acetate	ChEBI
2-Phenethyl acetic acid	Generator
Acetate b-phenylethyl ester	Generator
Acetate beta-phenylethyl ester	Generator
Acetate β-phenylethyl ester	Generator
Acetic acid b-phenylethyl ester	Generator
Acetic acid β-phenylethyl ester	Generator
Acetate, 2-phenylethyl ester	Generator
Acetate, phenethyl ester	Generator
Benzylcarbinyl acetic acid	Generator
b-Phenethyl acetate	Generator
b-Phenethyl acetic acid	Generator
beta-Phenethyl acetic acid	Generator
Β-phenethyl acetate	Generator
Β-phenethyl acetic acid	Generator
b-Phenylethyl acetate	Generator
b-Phenylethyl acetic acid	Generator
beta-Phenylethyl acetic acid	Generator
Β-phenylethyl acetate	Generator
Β-phenylethyl acetic acid	Generator
Phenethyl alcohol, acetic acid	Generator
2-Phenylethyl acetic acid	Generator
2-Phenylethyl acetate, 9ci	HMDB
Acetic acid beta -phenylethyl ester	HMDB
beta -Phenethyl acetate	HMDB
beta -Phenylethyl acetate	HMDB
Ethanol, 2-phenyl-, acetate	HMDB
FEMA 2857	HMDB
Phenethyl acetate	HMDB
Phenylethyl acetate	HMDB
Phenylethyl acetate-beta	HMDB
6,7-Dehydrophysalin H	MeSH, HMDB
6-Deoxyphysalin H	MeSH, HMDB
Physalin H	MeSH

Chemical Formula

C₂₈H₃₁ClO₁₀

Average Mass

562.9930 Da

Monoisotopic Mass

562.16057 Da

IUPAC Name

14-chloro-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone

Traditional Name

14-chloro-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone

CAS Registry Number

Not Available

SMILES

CC12OC(=O)C3(O)CCC4C(CC(O)C5(Cl)CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

InChI Identifier

InChI=1S/C28H31ClO10/c1-22-10-17-24(3)28-18(22)19(32)27(39-28,36-11-14(22)20(33)37-17)13-9-16(31)25(29)7-4-5-15(30)23(25,2)12(13)6-8-26(28,35)21(34)38-24/h4-5,12-14,16-18,31,35H,6-11H2,1-3H3

InChI Key

YNEPXUIPALKHAU-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
Alkekengi officinarum var. franchetii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetate ester (CHEBI:31988 )

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	1.56	ALOGPS
logP	2.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.79 m³·mol⁻¹	ChemAxon
Polarizability	53.53 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033945

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7654

PDB ID

Not Available

ChEBI ID

31988

Good Scents ID

Not Available

References

General References

Londesborough J, Dresel M, Gibson B, Juvonen R, Holopainen U, Mikkelson A, Seppanen-Laakso T, Viljanen K, Virtanen H, Wilpola A, Hofmann T, Wilhelmson A: Analysis of beers from an 1840s' shipwreck. J Agric Food Chem. 2015 Mar 11;63(9):2525-36. doi: 10.1021/jf5052943. Epub 2015 Feb 26. [PubMed:25664918 ]
Stribny J, Gamero A, Perez-Torrado R, Querol A: Saccharomyces kudriavzevii and Saccharomyces uvarum differ from Saccharomyces cerevisiae during the production of aroma-active higher alcohols and acetate esters using their amino acidic precursors. Int J Food Microbiol. 2015 Jul 16;205:41-6. doi: 10.1016/j.ijfoodmicro.2015.04.003. Epub 2015 Apr 8. [PubMed:25886016 ]

Showing NP-Card for Physalin H (NP0137009)

MOL for NP0137009 (Physalin H)

3D MOL for NP0137009 (Physalin H)

3D SDF for NP0137009 (Physalin H)

3D-SDF for NP0137009 (Physalin H)

PDB for NP0137009 (Physalin H)

3D PDB for NP0137009 (Physalin H)

SMILES for NP0137009 (Physalin H)

INCHI for NP0137009 (Physalin H)

Structure for NP0137009 (Physalin H)

3D Structure for NP0137009 (Physalin H)