NP-MRD: Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate (NP0245184)

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Record Information

Version

1.0

Created at

2022-09-07 06:10:05 UTC

Updated at

2022-09-07 06:10:05 UTC

NP-MRD ID

NP0245184

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(3R)-3-Acetoxyoctadecanoic acid (1S)-1-(acetoxymethyl)-2-hydroxyethyl ester 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)octadecanoate is found in Paulownia tomentosa. Based on a literature review very few articles have been published on (3R)-3-Acetoxyoctadecanoic acid (1S)-1-(acetoxymethyl)-2-hydroxyethyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208102D          

 32 31  0  0  1  0            999 V2000
   10.9461    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072208102D          

 32 31  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0245184

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H46O7/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(31-22(3)28)18-25(29)32-24(19-26)20-30-21(2)27/h23-24,26H,4-20H2,1-3H3/t23-,24+/m1/s1

> <INCHI_KEY>
WYYNBKNXTZIOIR-RPWUZVMVSA-N

> <FORMULA>
C25H46O7

> <MOLECULAR_WEIGHT>
458.636

> <EXACT_MASS>
458.324353821

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.06526248628529

> <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)octadecanoate

> <JCHEM_LOGP>
5.622616963333334

> <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>
123.12799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      20.433  13.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.766  14.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.100  13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.434  14.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.767  13.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.101  14.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.435  13.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.768  14.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.102  13.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.436  14.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.769  13.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.103  14.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.437  13.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.770  14.107   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.104  13.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.438  14.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.772  13.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.105  14.107   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      43.105  15.647   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      44.439  13.337   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      45.773  14.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.773  15.647   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      47.106  16.417   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      47.106  13.337   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      48.440  14.107   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      49.774  13.337   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      51.107  14.107   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      49.774  11.797   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      40.438  15.647   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      39.104  16.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.770  15.647   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      39.104  17.957   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   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-Acetoxyoctadecanoate (1S)-1-(acetoxymethyl)-2-hydroxyethyl ester	Generator

Chemical Formula

C₂₅H₄₆O₇

Average Mass

458.6360 Da

Monoisotopic Mass

458.32435 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H46O7/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(31-22(3)28)18-25(29)32-24(19-26)20-30-21(2)27/h23-24,26H,4-20H2,1-3H3/t23-,24+/m1/s1

InChI Key

WYYNBKNXTZIOIR-RPWUZVMVSA-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	5.62	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	24	ChemAxon
Refractivity	123.13 m³·mol⁻¹	ChemAxon
Polarizability	55.07 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

101491180

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)octadecanoate (NP0245184)

MOL for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

3D MOL for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

3D SDF for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

3D-SDF for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

PDB for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

3D PDB for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

SMILES for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

INCHI for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

Structure for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)

3D Structure for NP0245184 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r)-3-(acetyloxy)octadecanoate)