NP-MRD: Showing NP-Card for 2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid (NP0169485)

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Record Information

Version

2.0

Created at

2022-09-03 05:26:46 UTC

Updated at

2022-09-03 05:26:47 UTC

NP-MRD ID

NP0169485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid

Description

2-{[2-Hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid belongs to the class of organic compounds known as 1-alkyl,3-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 3-positions through an ether and an ester linkage, respectively. 2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid is found in Sargassum fulvellum. 2-{[2-Hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512242D          

 33 32  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1533004241512242D          

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 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC=CCC=CCCCCCCCCCC(=O)OCC(O)COCC(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)33-23-25(28)22-32-21-24(2)27(30)31/h7-8,10-11,25,28H,2-6,9,12-23H2,1H3,(H,30,31)

> <INCHI_KEY>
QPYZRDNMEPOLSA-UHFFFAOYSA-N

> <FORMULA>
C27H46O6

> <MOLECULAR_WEIGHT>
466.659

> <EXACT_MASS>
466.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.29365391360822

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid

> <ALOGPS_LOGP>
6.87

> <JCHEM_LOGP>
6.9459014240000005

> <ALOGPS_LOGS>
-6.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.655179787510647

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.918708918650356

> <JCHEM_PKA_STRONGEST_BASIC>
-3.387050134910517

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
134.65779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.811  18.369   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.144  17.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.144  16.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.478  15.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.478  13.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.812  12.979   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.812  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.145  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.479  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.813  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      30.483  11.439   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      33.150  12.979   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      35.818  11.439   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      38.485  12.979   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      39.819   9.129   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                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoate	Generator

Chemical Formula

C₂₇H₄₆O₆

Average Mass

466.6590 Da

Monoisotopic Mass

466.32944 Da

IUPAC Name

2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid

Traditional Name

2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCCCCCCCCCC(=O)OCC(O)COCC(=C)C(O)=O

InChI Identifier

InChI=1S/C27H46O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)33-23-25(28)22-32-21-24(2)27(30)31/h7-8,10-11,25,28H,2-6,9,12-23H2,1H3,(H,30,31)

InChI Key

QPYZRDNMEPOLSA-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
Sargassum fulvellum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,3-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 3-positions through an ether and an ester linkage, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1-alkyl,3-acylglycerols

Alternative Parents

Substituents

1-alkyl,3-acylglycerol
Fatty acid ester
Glycerol ether
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	6.87	ALOGPS
logP	6.95	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	134.66 m³·mol⁻¹	ChemAxon
Polarizability	56.29 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

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-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid (NP0169485)

MOL for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

3D MOL for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

3D SDF for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

3D-SDF for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

PDB for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

3D PDB for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

SMILES for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

INCHI for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

Structure for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)

3D Structure for NP0169485 (2-{[2-hydroxy-3-(icosa-11,14-dienoyloxy)propoxy]methyl}prop-2-enoic acid)