NP-MRD: Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate (NP0258025)

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Record Information

Version

2.0

Created at

2022-09-07 23:18:55 UTC

Updated at

2022-09-07 23:18:55 UTC

NP-MRD ID

NP0258025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate

Description

1-O-Acetyl-2-O-[(R)-3-acetoxyicosanoyl]-L-glycerol belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate is found in Paulownia tomentosa. Based on a literature review very few articles have been published on 1-O-Acetyl-2-O-[(R)-3-acetoxyicosanoyl]-L-glycerol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201182D          

 34 33  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082201182D          

 34 33  0  0  1  0            999 V2000
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 18 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0258025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCC[C@H](CC(=O)O[C@@H](CO)COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H50O7/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(33-24(3)30)20-27(31)34-26(21-28)22-32-23(2)29/h25-26,28H,4-22H2,1-3H3/t25-,26+/m1/s1

> <INCHI_KEY>
RZQVDEUOJAHMQM-FTJBHMTQSA-N

> <FORMULA>
C27H50O7

> <MOLECULAR_WEIGHT>
486.69

> <EXACT_MASS>
486.35565395

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.29807761541225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R)-3-(acetyloxy)icosanoate

> <JCHEM_LOGP>
6.511754293333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.577782250570237

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9834780436005772

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
132.32999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R)-3-(acetyloxy)icosanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      22.743  14.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.076  15.440   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.410  14.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.744  15.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.077  14.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.411  15.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.745  14.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.078  15.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.412  14.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.746  15.440   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.079  14.670   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.413  15.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.747  14.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.080  15.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.414  14.670   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.748  15.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.082  14.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.415  15.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.749  14.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      48.083  15.440   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      48.083  16.980   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      49.416  14.670   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      50.750  15.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      50.750  16.980   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      52.084  17.750   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      52.084  14.670   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      53.417  15.440   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      54.751  14.670   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      56.085  15.440   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      54.751  13.130   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      45.415  16.980   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      44.082  17.750   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      42.748  16.980   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      44.082  19.290   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   18   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₅₀O₇

Average Mass

486.6900 Da

Monoisotopic Mass

486.35565 Da

IUPAC Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R)-3-(acetyloxy)icosanoate

Traditional Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R)-3-(acetyloxy)icosanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC[C@H](CC(=O)O[C@@H](CO)COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C27H50O7/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(33-24(3)30)20-27(31)34-26(21-28)22-32-23(2)29/h25-26,28H,4-22H2,1-3H3/t25-,26+/m1/s1

InChI Key

RZQVDEUOJAHMQM-FTJBHMTQSA-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
Paulownia tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
1,2-acyl-sn-glycerol
Diacylglycerol
Diradylglycerol
Tricarboxylic acid or derivatives
Fatty acid ester
Glycerolipid
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	6.51	ChemAxon
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	132.33 m³·mol⁻¹	ChemAxon
Polarizability	59.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

102025024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate (NP0258025)

MOL for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

3D MOL for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

3D SDF for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

3D-SDF for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

PDB for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

3D PDB for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

SMILES for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

INCHI for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

Structure for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)

3D Structure for NP0258025 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate)