NP-MRD: Showing NP-Card for 5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid (NP0323068)

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Record Information

Version

2.0

Created at

2022-09-12 02:15:48 UTC

Updated at

2022-09-12 02:15:48 UTC

NP-MRD ID

NP0323068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid

Description

5-[(6-{[(2-Carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid is found in Lemna aequinoctialis. 5-[(6-{[(2-Carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251502372D          

 35 35  0  0  0  0            999 V2000
    3.4149    0.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2546   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -1.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251502372D          

 35 35  0  0  0  0            999 V2000
    3.4149    0.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0323068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC=CCC=CCC(=O)C(CCCC(O)=O)OC1OC(COC(=O)CC(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O12/c1-2-3-4-5-6-7-9-14(24)15(10-8-11-17(25)26)34-23-22(32)21(31)20(30)16(35-23)13-33-19(29)12-18(27)28/h3-4,6-7,15-16,20-23,30-32H,2,5,8-13H2,1H3,(H,25,26)(H,27,28)

> <INCHI_KEY>
ZSGDXXZGFQZSOT-UHFFFAOYSA-N

> <FORMULA>
C23H34O12

> <MOLECULAR_WEIGHT>
502.513

> <EXACT_MASS>
502.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.742874464451916

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.155836698999999

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.064235451083113

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3287477903696865

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490854936005865

> <JCHEM_POLAR_SURFACE_AREA>
197.11999999999998

> <JCHEM_REFRACTIVITY>
120.15729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.375   0.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.862   0.722   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.854  -0.442   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.342  -0.151   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -1.316   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.838  -2.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.830  -3.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.846  -5.681   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.854  -4.517   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.350  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862  -7.427   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.870  -6.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.383  -6.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.391  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.887  -3.935   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.903  -5.681   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.342  -8.300   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.846  -9.755   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.358 -10.047   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.862 -11.502   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.375 -11.793   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.383 -10.629   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.895 -10.920   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.399 -12.375   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.903  -9.755   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.415 -10.047   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.919 -11.502   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.424  -8.882   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.854 -12.666   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.358 -14.121   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.342 -12.375   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334 -13.539   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.838 -10.920   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.326 -10.629   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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   19   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Value	Source
5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoate	Generator

Chemical Formula

C₂₃H₃₄O₁₂

Average Mass

502.5130 Da

Monoisotopic Mass

502.20503 Da

IUPAC Name

5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid

Traditional Name

5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid

CAS Registry Number

Not Available

SMILES

CCC=CCC=CCC(=O)C(CCCC(O)=O)OC1OC(COC(=O)CC(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C23H34O12/c1-2-3-4-5-6-7-9-14(24)15(10-8-11-17(25)26)34-23-22(32)21(31)20(30)16(35-23)13-33-19(29)12-18(27)28/h3-4,6-7,15-16,20-23,30-32H,2,5,8-13H2,1H3,(H,25,26)(H,27,28)

InChI Key

ZSGDXXZGFQZSOT-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
Lemna aequinoctialis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Sugar acid
1,3-dicarbonyl compound
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Carboxylic acid
Polyol
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
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	0.93	ALOGPS
logP	1.16	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	197.12 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	120.16 m³·mol⁻¹	ChemAxon
Polarizability	50.74 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 5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid (NP0323068)

MOL for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

3D MOL for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

3D SDF for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

3D-SDF for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

PDB for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

3D PDB for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

SMILES for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

INCHI for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

Structure for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)

3D Structure for NP0323068 (5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-6-oxotetradeca-8,11-dienoic acid)