NP-MRD: Showing NP-Card for 1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate (NP0321781)

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Record Information

Version

2.0

Created at

2022-09-12 00:10:11 UTC

Updated at

2022-09-12 00:10:11 UTC

NP-MRD ID

NP0321781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate

Description

1,3-Dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate 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 3,9-bis(acetyloxy)icosanoate is found in Paulownia tomentosa. 1,3-Dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522042D          

 35 34  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171522042D          

 35 34  0  0  0  0            999 V2000
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   11.4235  -12.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7535  -12.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795  -12.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3305  -12.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1544  -11.6291    0.0000 C   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  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC(CCCCCC(CC(=O)OC(CO)CO)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H50O8/c1-4-5-6-7-8-9-10-11-13-16-24(33-22(2)30)17-14-12-15-18-25(34-23(3)31)19-27(32)35-26(20-28)21-29/h24-26,28-29H,4-21H2,1-3H3

> <INCHI_KEY>
LLNPHELCYPYJCB-UHFFFAOYSA-N

> <FORMULA>
C27H50O8

> <MOLECULAR_WEIGHT>
502.689

> <EXACT_MASS>
502.35056857

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
59.69149934153263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
5.125035766333333

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979617396788388

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278370867040358

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9827700626531204

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
133.99949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         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  C   UNK     0      18.248 -26.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.646 -26.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.904 -27.035   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.302 -26.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.561 -27.277   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.959 -26.631   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      25.099 -25.098   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      26.217 -27.519   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      27.615 -26.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.873 -27.761   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.272 -27.116   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      27.755 -25.340   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      29.153 -24.694   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.442 -24.856   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      21.184 -23.968   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      19.786 -24.613   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      21.324 -22.434   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.473 -24.129   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.215 -23.241   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.817 -23.887   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.355 -21.708   0.000  0.00  0.00           C+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   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26                                                            
CONECT   28   18   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   12   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

View in JSmol

Synonyms

Value	Source
1,3-Dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoic acid	Generator

Chemical Formula

C₂₇H₅₀O₈

Average Mass

502.6890 Da

Monoisotopic Mass

502.35057 Da

IUPAC Name

1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate

Traditional Name

1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(CCCCCC(CC(=O)OC(CO)CO)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C27H50O8/c1-4-5-6-7-8-9-10-11-13-16-24(33-22(2)30)17-14-12-15-18-25(34-23(3)31)19-27(32)35-26(20-28)21-29/h24-26,28-29H,4-21H2,1-3H3

InChI Key

LLNPHELCYPYJCB-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
Paulownia tomentosa	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Endocannabinoids

Sub Class

Not Available

Direct Parent

Endocannabinoids

Alternative Parents

Substituents

2-arachidonoylglycerol-skeleton
Fatty alcohol ester
Tricarboxylic acid or derivatives
2-acyl-sn-glycerol
Monoacylglycerol
Monoradylglycerol
Fatty acid ester
Glycerolipid
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
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	5.41	ALOGPS
logP	5.13	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	134 m³·mol⁻¹	ChemAxon
Polarizability	59.69 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 1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate (NP0321781)

MOL for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

3D MOL for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

3D SDF for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

3D-SDF for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

PDB for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

3D PDB for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

SMILES for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

INCHI for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

Structure for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)

3D Structure for NP0321781 (1,3-dihydroxypropan-2-yl 3,9-bis(acetyloxy)icosanoate)