NP-MRD: Showing NP-Card for (2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate (NP0243658)

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Record Information

Version

2.0

Created at

2022-09-07 04:15:29 UTC

Updated at

2022-09-07 04:15:29 UTC

NP-MRD ID

NP0243658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate

Description

(2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate is found in Lobophytum crassum. Based on a literature review very few articles have been published on (2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206152D          

 34 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072206152D          

 34 34  0  0  1  0            999 V2000
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   21.4597  -10.9639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.6343  -11.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6741  -10.7120    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0631  -11.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  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  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 19 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0243658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCOC[C@@H](COC(C)=O)O[C@@H]1OC[C@@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H50O8/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-31-18-22(19-32-21(2)27)34-26-25(30)24(29)23(28)20-33-26/h22-26,28-30H,3-20H2,1-2H3/t22-,23+,24+,25-,26-/m0/s1

> <INCHI_KEY>
UZWHSLHUBOMECU-ZLILOBPGSA-N

> <FORMULA>
C26H50O8

> <MOLECULAR_WEIGHT>
490.678

> <EXACT_MASS>
490.35056857

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.14853013316436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate

> <JCHEM_LOGP>
4.763460182333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.403155186998507

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.24604575779449

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806570161216

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
129.9552

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate

> <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      12.196 -24.135   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.803 -23.570   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.944 -22.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.410 -23.006   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.551 -21.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.017 -22.442   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.158 -21.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.624 -21.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.765 -20.842   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.231 -21.313   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.372 -20.278   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.838 -20.748   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.979 -19.713   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.445 -20.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.585 -19.149   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      33.052 -19.619   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      34.192 -18.585   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.659 -19.055   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.985 -20.560   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      34.844 -21.595   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      35.170 -23.100   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.636 -23.570   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      34.030 -24.135   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      36.799 -18.020   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      38.266 -18.491   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      39.406 -17.456   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      40.873 -17.926   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      41.199 -19.431   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      42.665 -19.902   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      40.058 -20.466   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      40.384 -21.971   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      38.592 -19.996   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      37.451 -21.030   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                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-(Hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetic acid	Generator

Chemical Formula

C₂₆H₅₀O₈

Average Mass

490.6780 Da

Monoisotopic Mass

490.35057 Da

IUPAC Name

(2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate

Traditional Name

(2S)-3-(hexadecyloxy)-2-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCOC[C@@H](COC(C)=O)O[C@@H]1OC[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H50O8/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-31-18-22(19-32-21(2)27)34-26-25(30)24(29)23(28)20-33-26/h22-26,28-30H,3-20H2,1-2H3/t22-,23+,24+,25-,26-/m0/s1

InChI Key

UZWHSLHUBOMECU-ZLILOBPGSA-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
Lobophytum crassum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Glycerol ether
Glycerolipid
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Polyol
Acetal
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.76	ChemAxon
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	129.96 m³·mol⁻¹	ChemAxon
Polarizability	59.15 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29213834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25053182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate (NP0243658)

MOL for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

3D MOL for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

3D SDF for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

3D-SDF for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

PDB for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

3D PDB for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

SMILES for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

INCHI for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

Structure for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)

3D Structure for NP0243658 ((2s)-3-(hexadecyloxy)-2-{[(2s,3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}propyl acetate)