NP-MRD: Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one (NP0245720)

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Record Information

Version

2.0

Created at

2022-09-07 06:54:32 UTC

Updated at

2022-09-07 06:54:32 UTC

NP-MRD ID

NP0245720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

Description

1-Phenylethyl formate, also known as a-methylbenzyl formate or fema 2688, belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. 1-Phenylethyl formate is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Phenylethyl formate is a floral, gardenia, and green tasting compound. 15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one is found in Physalis philadelphica. Outside of the human body,.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307172D          

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M  END

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M  END


  Mrv0541 05061307172D          

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 19  6  1  0  0  0  0
 20  7  1  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24 14  1  0  0  0  0
 25  3  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 25 23  1  0  0  0  0
 26  4  1  0  0  0  0
 26 16  1  0  0  0  0
 26 19  1  0  0  0  0
 27  5  1  0  0  0  0
 27 21  1  0  0  0  0
 27 23  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 28 26  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  2  0  0  0  0
 31 20  1  0  0  0  0
 32 24  2  0  0  0  0
 33 27  1  0  0  0  0
 34 21  1  0  0  0  0
 34 24  1  0  0  0  0
 35 22  1  0  0  0  0
 35 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(OC(=O)C1C)C(C)(O)C1C(O)CC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O7/c1-13-10-21(34-24(32)14(13)2)27(5,33)23-18(29)12-17-15-11-22-28(35-22)20(31)7-6-19(30)26(28,4)16(15)8-9-25(17,23)3/h6-7,13-18,20-23,29,31,33H,8-12H2,1-5H3

> <INCHI_KEY>
CZKZWDJWVZTWCF-UHFFFAOYSA-N

> <FORMULA>
C28H40O7

> <MOLECULAR_WEIGHT>
488.613

> <EXACT_MASS>
488.277403634

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
53.51633790708483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
2.3961742266666644

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.865691927998569

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.245040522489568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8738619986152534

> <JCHEM_POLAR_SURFACE_AREA>
116.59

> <JCHEM_REFRACTIVITY>
127.83249999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <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      16.157   7.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.996  10.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.431   4.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.223   5.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.631   7.551   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.051   8.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.161   6.546   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.526   9.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.215   5.330   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.945  10.615   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.000   6.275   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      11.580   7.972   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7   19                                                       
CONECT    7    6   20                                                       
CONECT    8    9   16                                                       
CONECT    9    8   25                                                       
CONECT   10   13   21                                                       
CONECT   11   15   22                                                       
CONECT   12   17   18                                                       
CONECT   13    1   10   14                                                  
CONECT   14    2   13   24                                                  
CONECT   15   11   16   17                                                  
CONECT   16    8   15   26                                                  
CONECT   17   12   15   25                                                  
CONECT   18   12   23   29                                                  
CONECT   19    6   26   30                                                  
CONECT   20    7   28   31                                                  
CONECT   21   10   27   34                                                  
CONECT   22   11   28   35                                                  
CONECT   23   18   25   27                                                  
CONECT   24   14   32   34                                                  
CONECT   25    3    9   17   23                                             
CONECT   26    4   16   19   28                                             
CONECT   27    5   21   23   33                                             
CONECT   28   20   22   26   35                                             
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   20                                                            
CONECT   32   24                                                            
CONECT   33   27                                                            
CONECT   34   21   24                                                       
CONECT   35   22   28                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
1-Phenylethyl formic acid	Generator
a-Methylbenzyl formate	HMDB
alpha-Methylbenzyl formate	HMDB
Benzenemethanol, alpha-methyl-, formate	HMDB
Benzyl alcohol, alpha-methyl-, formate	HMDB
FEMA 2688	HMDB
Styralyl formate	HMDB
5,6b-Epoxy-4b,16b,20R-trihydroxy-1-oxo-5b,22R,24R,25R-with-2-enolide	HMDB

Chemical Formula

C₂₈H₄₀O₇

Average Mass

488.6130 Da

Monoisotopic Mass

488.27740 Da

IUPAC Name

15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

Traditional Name

15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

CC1CC(OC(=O)C1C)C(C)(O)C1C(O)CC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H40O7/c1-13-10-21(34-24(32)14(13)2)27(5,33)23-18(29)12-17-15-11-22-28(35-22)20(31)7-6-19(30)26(28,4)16(15)8-9-25(17,23)3/h6-7,13-18,20-23,29,31,33H,8-12H2,1-5H3

InChI Key

CZKZWDJWVZTWCF-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
Physalis philadelphica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
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

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	1.85	ALOGPS
logP	2.4	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.83 m³·mol⁻¹	ChemAxon
Polarizability	53.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037715

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016844

KNApSAcK ID

Not Available

Chemspider ID

307171

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

346286

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one (NP0245720)

MOL for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D MOL for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D SDF for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D-SDF for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

PDB for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D PDB for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

SMILES for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

INCHI for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

Structure for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D Structure for NP0245720 (15-[1-(4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)