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Showing NP-Card for 1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate (NP0224725)

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Record Information
Version2.0
Created at2022-09-06 03:13:50 UTC
Updated at2022-09-06 03:13:50 UTC
NP-MRD IDNP0224725
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate
Description2-O-[(3r,7r)-3,7-dihydroxy-eicosanoyl]-glycerol belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail. 1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate is found in Paulownia tomentosa. Based on a literature review very few articles have been published on 2-O-[(3r,7r)-3,7-dihydroxy-eicosanoyl]-glycerol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)


  Mrv1652309062205132D          

 29 28  0  0  1  0            999 V2000
   -0.1855  -13.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634  -13.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375  -13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865  -13.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605  -13.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095  -13.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0836  -13.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326  -13.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066  -13.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2556  -13.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297  -14.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6786  -13.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3527  -14.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1017  -13.8776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1766  -13.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757  -14.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5247  -14.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1988  -14.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9478  -14.1371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0227  -13.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6218  -14.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3708  -14.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4457  -13.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0449  -14.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7938  -14.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4679  -14.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2169  -14.5263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8687  -13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6177  -13.2290    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  1  0  0  0
 14 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  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
Download

3D MOL for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)

Download
3D SDF for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)

  Mrv1652309062205132D          

 29 28  0  0  1  0            999 V2000
   -0.1855  -13.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634  -13.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375  -13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865  -13.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605  -13.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095  -13.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0836  -13.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326  -13.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066  -13.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2556  -13.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297  -14.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6786  -13.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3527  -14.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1017  -13.8776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1766  -13.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757  -14.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5247  -14.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1988  -14.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9478  -14.1371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0227  -13.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6218  -14.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3708  -14.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4457  -13.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0449  -14.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7938  -14.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4679  -14.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2169  -14.5263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8687  -13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6177  -13.2290    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  1  0  0  0
 14 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  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224725

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC[C@@H](O)CCC[C@@H](O)CC(=O)OC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H46O6/c1-2-3-4-5-6-7-8-9-10-11-12-14-20(26)15-13-16-21(27)17-23(28)29-22(18-24)19-25/h20-22,24-27H,2-19H2,1H3/t20-,21-/m1/s1

> <INCHI_KEY>
VYIOOFWPGOEUIJ-NHCUHLMSSA-N

> <FORMULA>
C23H46O6

> <MOLECULAR_WEIGHT>
418.615

> <EXACT_MASS>
418.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.910324408327725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (3R,7R)-3,7-dihydroxyicosanoate

> <JCHEM_LOGP>
4.242784945666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.764134256975805

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.202879089462584

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2748465182187476

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
115.69649999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dihydroxypropan-2-yl (3R,7R)-3,7-dihydroxyicosanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)
Download
PDB for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.346 -25.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.052 -24.452   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310 -25.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.708 -24.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.966 -25.582   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.364 -24.936   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.623 -25.824   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.021 -25.178   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.279 -26.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.677 -25.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.935 -26.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.333 -25.663   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.592 -26.551   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.990 -25.905   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.130 -24.371   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.248 -26.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.646 -26.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.904 -27.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.302 -26.389   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      22.442 -24.856   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      23.561 -27.277   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.959 -26.631   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.099 -25.098   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.217 -27.519   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      27.615 -26.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.873 -27.761   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      30.272 -27.116   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      27.755 -25.340   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      29.153 -24.694   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   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

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3D PDB for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)
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SMILES for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)
CCCCCCCCCCCCC[C@@H](O)CCC[C@@H](O)CC(=O)OC(CO)CO
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INCHI for NP0224725 (1,3-dihydroxypropan-2-yl (3r,7r)-3,7-dihydroxyicosanoate)
InChI=1S/C23H46O6/c1-2-3-4-5-6-7-8-9-10-11-12-14-20(26)15-13-16-21(27)17-23(28)29-22(18-24)19-25/h20-22,24-27H,2-19H2,1H3/t20-,21-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H46O6
Average Mass418.6150 Da
Monoisotopic Mass418.32944 Da
IUPAC Name1,3-dihydroxypropan-2-yl (3R,7R)-3,7-dihydroxyicosanoate
Traditional Name1,3-dihydroxypropan-2-yl (3R,7R)-3,7-dihydroxyicosanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC[C@@H](O)CCC[C@@H](O)CC(=O)OC(CO)CO
InChI Identifier
InChI=1S/C23H46O6/c1-2-3-4-5-6-7-8-9-10-11-12-14-20(26)15-13-16-21(27)17-23(28)29-22(18-24)19-25/h20-22,24-27H,2-19H2,1H3/t20-,21-/m1/s1
InChI KeyVYIOOFWPGOEUIJ-NHCUHLMSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Paulownia tomentosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassEndocannabinoids  
Sub ClassNot Available
Direct ParentEndocannabinoids  
Alternative Parents
Substituents
  • 2-arachidonoylglycerol-skeleton
    • 

  • Long chain fatty alcohol
    • 

  • Fatty alcohol
    • 

  • 2-acyl-sn-glycerol
    • 

  • Monoradylglycerol
    • 

  • Monoacylglycerol
    • 

  • Beta-hydroxy acid
    • 

  • Glycerolipid
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Hydroxy acid
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.24ChemAxon
pKa (Strongest Acidic)14.2ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity115.7 m³·mol⁻¹ChemAxon
Polarizability51.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129834624  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]