NP-MRD: Showing NP-Card for 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate (NP0170276)

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Record Information

Version

2.0

Created at

2022-09-03 06:24:16 UTC

Updated at

2022-09-03 06:24:16 UTC

NP-MRD ID

NP0170276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate

Description

2-Hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate belongs to the class of organic compounds known as glycosylmonoacylglycerols. These are glycosylglycerols carrying exactly one fatty acyl chain attached to the glycerol moiety through an ester linkage. 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate is found in Cibotium barometz. 2-Hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500212D          

 36 36  0  0  0  0            999 V2000
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    0.7145   -5.3625    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


  Mrv1533004201500212D          

 36 36  0  0  0  0            999 V2000
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   16.4328   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -10.3125    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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  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  2  0  0  0  0
 18 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  1  0  0  0  0
 24 25  1  0  0  0  0
 25 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
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC=CCC=CCCCCCCCC(=O)OCC(O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(30)34-19-21(29)20-35-27-26(33)25(32)24(31)22(18-28)36-27/h6-7,9-10,21-22,24-29,31-33H,2-5,8,11-20H2,1H3

> <INCHI_KEY>
LBHUIJRTHBBWHP-UHFFFAOYSA-N

> <FORMULA>
C27H48O9

> <MOLECULAR_WEIGHT>
516.672

> <EXACT_MASS>
516.329833126

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.17546170334112

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.4764982506666673

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.083796095114906

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195332284406508

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422314084

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
137.956

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.672 -18.480   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.673 -14.630   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      25.340 -16.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      26.674 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      28.007 -16.170   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      29.341 -16.940   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.675 -16.170   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      30.675 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      29.341 -18.480   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      30.675 -19.250   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      28.007 -20.790   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      25.340 -19.250   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoic acid	Generator

Chemical Formula

C₂₇H₄₈O₉

Average Mass

516.6720 Da

Monoisotopic Mass

516.32983 Da

IUPAC Name

2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate

Traditional Name

2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCCCCCCCC(=O)OCC(O)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H48O9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(30)34-19-21(29)20-35-27-26(33)25(32)24(31)22(18-28)36-27/h6-7,9-10,21-22,24-29,31-33H,2-5,8,11-20H2,1H3

InChI Key

LBHUIJRTHBBWHP-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
Cibotium barometz	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylmonoacylglycerols. These are glycosylglycerols carrying exactly one fatty acyl chain attached to the glycerol moiety through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Glycosylglycerols

Direct Parent

Glycosylmonoacylglycerols

Alternative Parents

Substituents

Glycosylmonoacylglycerol
Octadecanoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Fatty acyl
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Polyol
Carbonyl group
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	3.81	ALOGPS
logP	3.48	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	137.96 m³·mol⁻¹	ChemAxon
Polarizability	59.18 Å³	ChemAxon
Number of Rings	1	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate (NP0170276)

MOL for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

3D MOL for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

3D SDF for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

3D-SDF for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

PDB for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

3D PDB for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

SMILES for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

INCHI for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

Structure for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)

3D Structure for NP0170276 (2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl octadeca-9,12-dienoate)