NP-MRD: Showing NP-Card for Triricinolein (NP0337349)

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Record Information

Version

2.0

Created at

2024-09-11 10:26:39 UTC

Updated at

2024-09-11 10:26:39 UTC

NP-MRD ID

NP0337349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triricinolein

Description

It was first documented in 2006 (PMID: 19127716). Based on a literature review a small amount of articles have been published on Triricinolein (PMID: 30295712) (PMID: 22319559) (PMID: 16555475).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262312582D          

 66 65  0  0  0  0            999 V2000
   23.6814    2.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9288    2.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 05262312582D          

 66 65  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0337349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CC(O)CCCCCC)OC(=O)CCCCCCC\C=C\CC(O)CCCCCC

> <INCHI_IDENTIFIER>
InChI=1/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27+

> <INCHI_KEY>
ZEMPKEQAKRGZGQ-YAFIDQONNA-N

> <FORMULA>
C57H104O9

> <MOLECULAR_WEIGHT>
933.45

> <EXACT_MASS>
932.768034929

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
170

> <JCHEM_AVERAGE_POLARIZABILITY>
121.03516418372472

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate

> <JCHEM_LOGP>
16.345639123333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.401256348683585

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.401256348683585

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8339684132006674

> <JCHEM_POLAR_SURFACE_AREA>
139.58999999999997

> <JCHEM_REFRACTIVITY>
277.25459999999987

> <JCHEM_ROTATABLE_BOND_COUNT>
53

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      44.205   4.253   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.467   1.820   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.830 -16.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      42.800   4.884   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.218   2.721   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.674 -15.213   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.552   3.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.186   2.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.923 -14.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.147   4.614   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.435   2.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.767 -12.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.279   6.236   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.489   6.236   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.137  -3.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.123   7.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.894   5.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.386  -2.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.030   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.294  -4.579   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.718   8.399   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.142   6.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.230  -0.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.186   3.803   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.835   5.965   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.045  -5.480   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.469   7.498   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.547   5.876   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.479   0.288   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.898   3.713   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.840   2.361   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.015 -11.879   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      33.591   3.172   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.586   5.064   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.201  -7.012   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      29.064   8.128   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.796   6.777   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.323   1.820   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      37.493   4.343   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.089   3.262   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.859 -10.346   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      34.840   4.073   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.742   3.532   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.952  -7.913   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      27.815   7.227   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      17.201   6.146   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      21.572   2.721   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.757   7.588   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      21.103   7.317   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      36.245   3.442   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.494   2.631   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      16.108  -9.445   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.508   6.687   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      26.411   7.858   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      18.450   7.047   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      21.416   4.253   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      36.401   1.910   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       5.650   1.099   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      17.513 -10.076   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      26.254   9.390   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      18.294   8.579   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      20.011   4.884   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      25.162   6.957   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      19.854   6.416   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      22.664   5.154   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   31                                                       
CONECT   11    8   32                                                       
CONECT   12    9   33                                                       
CONECT   13   16   19                                                       
CONECT   14   17   20                                                       
CONECT   15   18   21                                                       
CONECT   16   13   22                                                       
CONECT   17   14   23                                                       
CONECT   18   15   24                                                       
CONECT   19   13   25                                                       
CONECT   20   14   26                                                       
CONECT   21   15   27                                                       
CONECT   22   16   28                                                       
CONECT   23   17   29                                                       
CONECT   24   18   30                                                       
CONECT   25   19   34                                                       
CONECT   26   20   35                                                       
CONECT   27   21   36                                                       
CONECT   28   22   37                                                       
CONECT   29   23   38                                                       
CONECT   30   24   39                                                       
CONECT   31   10   40                                                       
CONECT   32   11   41                                                       
CONECT   33   12   42                                                       
CONECT   34   25   43                                                       
CONECT   35   26   44                                                       
CONECT   36   27   45                                                       
CONECT   37   28   46                                                       
CONECT   38   29   47                                                       
CONECT   39   30   48                                                       
CONECT   40   31   51                                                       
CONECT   41   32   52                                                       
CONECT   42   33   53                                                       
CONECT   43   34   51                                                       
CONECT   44   35   52                                                       
CONECT   45   36   53                                                       
CONECT   46   37   55                                                       
CONECT   47   38   56                                                       
CONECT   48   39   57                                                       
CONECT   49   54   64                                                       
CONECT   50   54   65                                                       
CONECT   51   40   43   58                                                  
CONECT   52   41   44   59                                                  
CONECT   53   42   45   60                                                  
CONECT   54   49   50   66                                                  
CONECT   55   46   61   64                                                  
CONECT   56   47   62   65                                                  
CONECT   57   48   63   66                                                  
CONECT   58   51                                                            
CONECT   59   52                                                            
CONECT   60   53                                                            
CONECT   61   55                                                            
CONECT   62   56                                                            
CONECT   63   57                                                            
CONECT   64   49   55                                                       
CONECT   65   50   56                                                       
CONECT   66   54   57                                                       
MASTER        0    0    0    0    0    0    0    0   66    0  130    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₇H₁₀₄O₉

Average Mass

933.4500 Da

Monoisotopic Mass

932.76803 Da

IUPAC Name

2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate

Traditional Name

2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CC(O)CCCCCC)OC(=O)CCCCCCC\C=C\CC(O)CCCCCC

InChI Identifier

InChI=1/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27+

InChI Key

ZEMPKEQAKRGZGQ-YAFIDQONNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	16.35	ChemAxon
pKa (Strongest Acidic)	18.4	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	53	ChemAxon
Refractivity	277.25 m³·mol⁻¹	ChemAxon
Polarizability	121.04 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

Ricinolein

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Du J, Gong C, Pei X, Zhao H, Xu X: Analysis of Triacylglycerols in Castor Oil Through Liquid Chromatography-Mass Spectrometry Based on Fourier Transform-Ion Cyclotron Resonance-Mass Spectrometry and Gas Chromatography-Mass Spectrometry. J Chromatogr Sci. 2019 Feb 1;57(2):108-115. doi: 10.1093/chromsci/bmy088. [PubMed:30295712 ]
Brown AP, Kroon JT, Swarbreck D, Febrer M, Larson TR, Graham IA, Caccamo M, Slabas AR: Tissue-specific whole transcriptome sequencing in castor, directed at understanding triacylglycerol lipid biosynthetic pathways. PLoS One. 2012;7(2):e30100. doi: 10.1371/journal.pone.0030100. Epub 2012 Feb 3. [PubMed:22319559 ]
Lin JT, Arcinas A, Harden LR, Fagerquist CK: Identification of (12-ricinoleoylricinoleoyl)diricinoleoylglycerol, an acylglycerol containing four acyl chains, in castor (Ricinus communis L.) oil by LC-ESI-MS. J Agric Food Chem. 2006 May 17;54(10):3498-504. doi: 10.1021/jf060150e. [PubMed:19127716 ]
Turner C, Wani S, Wong R, Lin JT, McKeon T: Lipase-catalyzed esterification of 2-monoricinolein for 1,2 (2,3)-diricinolein synthesis. Lipids. 2006 Jan;41(1):77-83. doi: 10.1007/s11745-006-5073-y. [PubMed:16555475 ]

Showing NP-Card for Triricinolein (NP0337349)

MOL for NP0337349 (Triricinolein)

3D MOL for NP0337349 (Triricinolein)

3D SDF for NP0337349 (Triricinolein)

3D-SDF for NP0337349 (Triricinolein)

PDB for NP0337349 (Triricinolein)

3D PDB for NP0337349 (Triricinolein)

SMILES for NP0337349 (Triricinolein)

INCHI for NP0337349 (Triricinolein)

Structure for NP0337349 (Triricinolein)

3D Structure for NP0337349 (Triricinolein)