NP-MRD: Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate (NP0215586)

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Record Information

Version

2.0

Created at

2022-09-05 15:15:14 UTC

Updated at

2022-09-05 15:15:15 UTC

NP-MRD ID

NP0215586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate

Description

1-O-acetyl-2-O-[(3r,7r)-3,7-bis(acetyloxy)octadecanoyl]-sn-glycerol belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate is found in Paulownia tomentosa. Based on a literature review very few articles have been published on 1-O-acetyl-2-O-[(3r,7r)-3,7-bis(acetyloxy)octadecanoyl]-sn-glycerol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217152D          

 36 35  0  0  1  0            999 V2000
   10.9461    7.1447    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


  Mrv1652309052217152D          

 36 35  0  0  1  0            999 V2000
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   20.9487    9.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052    8.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0908    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3763    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0908    9.6197    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  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
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 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
 26 28  2  0  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 12 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0215586

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O9/c1-5-6-7-8-9-10-11-12-13-15-24(34-22(3)30)16-14-17-25(35-23(4)31)18-27(32)36-26(19-28)20-33-21(2)29/h24-26,28H,5-20H2,1-4H3/t24-,25-,26+/m1/s1

> <INCHI_KEY>
UUMYGAVEBJQKTI-CYXNTTPDSA-N

> <FORMULA>
C27H48O9

> <MOLECULAR_WEIGHT>
516.672

> <EXACT_MASS>
516.329833126

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.25925095401307

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,7R)-3,7-bis(acetyloxy)octadecanoate

> <JCHEM_LOGP>
4.677023846666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.577782250570237

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9834780436005772

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000004

> <JCHEM_REFRACTIVITY>
133.94899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,7R)-3,7-bis(acetyloxy)octadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      20.433  13.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.766  14.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.100  13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.434  14.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.767  13.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.101  14.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.435  13.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.768  14.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.102  13.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.436  14.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.769  13.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.103  14.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.437  13.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.770  14.107   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.104  13.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.438  14.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.772  13.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.105  14.107   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      43.105  15.647   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      44.439  13.337   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      45.773  14.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.773  15.647   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      47.106  16.417   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      47.106  13.337   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      48.440  14.107   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      49.774  13.337   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      51.107  14.107   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      49.774  11.797   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      40.438  15.647   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      39.104  16.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.770  15.647   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      39.104  17.957   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      35.103  15.647   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      33.769  16.417   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      32.436  15.647   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      33.769  17.957   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   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   12   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₈O₉

Average Mass

516.6720 Da

Monoisotopic Mass

516.32983 Da

IUPAC Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,7R)-3,7-bis(acetyloxy)octadecanoate

Traditional Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,7R)-3,7-bis(acetyloxy)octadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC[C@H](CCC[C@H](CC(=O)O[C@@H](CO)COC(C)=O)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C27H48O9/c1-5-6-7-8-9-10-11-12-13-15-24(34-22(3)30)16-14-17-25(35-23(4)31)18-27(32)36-26(19-28)20-33-21(2)29/h24-26,28H,5-20H2,1-4H3/t24-,25-,26+/m1/s1

InChI Key

UUMYGAVEBJQKTI-CYXNTTPDSA-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 tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty alcohol ester
1,2-acyl-sn-glycerol
Diacylglycerol
Diradylglycerol
Fatty acid ester
Glycerolipid
Fatty acyl
Carboxylic acid ester
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
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	4.68	ChemAxon
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	133.95 m³·mol⁻¹	ChemAxon
Polarizability	59.26 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

101491181

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate (NP0215586)

MOL for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

3D MOL for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

3D SDF for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

3D-SDF for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

PDB for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

3D PDB for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

SMILES for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

INCHI for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

Structure for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)

3D Structure for NP0215586 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)octadecanoate)