Np mrd loader

Showing NP-Card for Triricinolein (NP0337349)

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Record Information
Version2.0
Created at2024-09-11 10:26:39 UTC
Updated at2024-09-11 10:26:39 UTC
NP-MRD IDNP0337349
Secondary Accession NumbersNone
Natural Product Identification
Common NameTriricinolein
DescriptionTriricinolein belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Triricinolein 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: 16555475).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0337349 (Triricinolein)


  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
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M  END
Download

3D MOL for NP0337349 (Triricinolein)

Download
3D SDF for NP0337349 (Triricinolein)

  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

$$$$

Download
3D-SDF for NP0337349 (Triricinolein)
Download
PDB for NP0337349 (Triricinolein)
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

Download
3D PDB for NP0337349 (Triricinolein)
Download
SMILES for NP0337349 (Triricinolein)
CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CC(O)CCCCCC)OC(=O)CCCCCCC\C=C\CC(O)CCCCCC
Download
INCHI for NP0337349 (Triricinolein)
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+
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC57H104O9
Average Mass933.4500 Da
Monoisotopic Mass932.76803 Da
IUPAC Name2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate
Traditional Name2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate
CAS Registry NumberNot 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 KeyZEMPKEQAKRGZGQ-YAFIDQONNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerolipids  
Sub ClassTriradylcglycerols  
Direct ParentTriacylglycerols  
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Fatty alcohol
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP16.35ChemAxon
pKa (Strongest Acidic)18.4ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.59 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity277.25 m³·mol⁻¹ChemAxon
Polarizability121.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
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 LinkRicinolein  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. 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  ] 
  3. 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  ]