NP-MRD: Showing NP-Card for TG(16:0/16:1(9Z)/18:0)[iso6] (NP0334134)

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Record Information

Version

2.0

Created at

2024-09-09 22:20:13 UTC

Updated at

2024-09-09 22:20:14 UTC

NP-MRD ID

NP0334134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

TG(16:0/16:1(9Z)/18:0)[iso6]

Description

TG(16:0/16:1(9Z)/18:0)[Iso6] is a monostearic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.E. Fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/16:1(9Z)/18:0)[Iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of palmitoleic acid at the C-2 position and one chain of stearic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (Www.Cyberlipid.Org, www.Wikipedia.Org) TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004261606212D          

 62 61  0  0  1  0            999 V2000
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M  END


  Mrv1572004261606212D          

 62 61  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0334134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C53H100O6/c1-4-7-10-13-16-19-22-25-26-29-31-34-37-40-43-46-52(55)58-49-50(59-53(56)47-44-41-38-35-32-28-24-21-18-15-12-9-6-3)48-57-51(54)45-42-39-36-33-30-27-23-20-17-14-11-8-5-2/h21,24,50H,4-20,22-23,25-49H2,1-3H3/b24-21+/t50-/m1/s1

> <INCHI_KEY>
YSNGWXHIKNKBNE-PZIDBCNXSA-N

> <FORMULA>
C53H100O6

> <MOLECULAR_WEIGHT>
833.377

> <EXACT_MASS>
832.75199094

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
159

> <JCHEM_AVERAGE_POLARIZABILITY>
112.53614257044826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(9E)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl octadecanoate

> <ALOGPS_LOGP>
10.69

> <JCHEM_LOGP>
19.451363357666665

> <ALOGPS_LOGS>
-7.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565867985366683

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
251.60890000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
51

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(9E)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl octadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-16         0                                  
HETATM    1  C   UNK     0      18.686  -9.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      69.366  -9.899   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      56.029  10.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.020 -10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      68.032 -10.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      56.029   8.581   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.354  -9.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      66.699  -9.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      54.696   7.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.687 -10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      65.365 -10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      54.696   6.271   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.021  -9.899   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      64.031  -9.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      53.362   5.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.355 -10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      62.698 -10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      53.362   3.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.688  -9.899   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      61.364  -9.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      52.028   3.191   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.022 -10.669   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      60.030 -10.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      52.028   1.651   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.356  -9.899   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.689 -10.669   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      58.697  -9.899   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      50.695   0.881   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.023  -9.899   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      57.363 -10.669   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.357 -10.669   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      50.695  -0.659   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      56.029  -9.899   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.690  -9.899   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      49.361  -1.429   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      54.696 -10.669   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      36.024 -10.669   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      49.361  -2.969   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      53.362  -9.899   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      37.358  -9.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      48.027  -3.739   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      52.028 -10.669   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      38.692 -10.669   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      48.027  -5.279   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      50.695  -9.899   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      40.025  -9.899   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      46.694  -6.049   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      46.694 -10.669   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      44.026 -10.669   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      45.360  -9.899   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      49.361 -10.669   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      41.359 -10.669   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      46.694  -7.589   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      49.361 -12.209   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      41.359 -12.209   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      48.027  -8.359   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      48.027  -9.899   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      42.693  -9.899   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      45.360  -8.359   0.000  0.00  0.00           O+0
HETATM   60  H   UNK     0      50.695   3.961   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      53.362   0.881   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      45.360 -11.439   0.000  0.00  0.00           H+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   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23                                                       
CONECT   21   18   24   60                                                  
CONECT   22   19   25                                                       
CONECT   23   20   27                                                       
CONECT   24   21   28   61                                                  
CONECT   25   22   26                                                       
CONECT   26   25   29                                                       
CONECT   27   23   30                                                       
CONECT   28   24   32                                                       
CONECT   29   26   31                                                       
CONECT   30   27   33                                                       
CONECT   31   29   34                                                       
CONECT   32   28   35                                                       
CONECT   33   30   36                                                       
CONECT   34   31   37                                                       
CONECT   35   32   38                                                       
CONECT   36   33   39                                                       
CONECT   37   34   40                                                       
CONECT   38   35   41                                                       
CONECT   39   36   42                                                       
CONECT   40   37   43                                                       
CONECT   41   38   44                                                       
CONECT   42   39   45                                                       
CONECT   43   40   46                                                       
CONECT   44   41   47                                                       
CONECT   45   42   51                                                       
CONECT   46   43   52                                                       
CONECT   47   44   53                                                       
CONECT   48   50   57                                                       
CONECT   49   50   58                                                       
CONECT   50   48   49   59   62                                             
CONECT   51   45   54   57                                                  
CONECT   52   46   55   58                                                  
CONECT   53   47   56   59                                                  
CONECT   54   51                                                            
CONECT   55   52                                                            
CONECT   56   53                                                            
CONECT   57   48   51                                                       
CONECT   58   49   52                                                       
CONECT   59   50   53                                                       
CONECT   60   21                                                            
CONECT   61   24                                                            
CONECT   62   50                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  122    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(9E)-Hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl octadecanoic acid	Generator

Chemical Formula

C₅₃H₁₀₀O₆

Average Mass

833.3770 Da

Monoisotopic Mass

832.75199 Da

IUPAC Name

(2R)-2-[(9E)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl octadecanoate

Traditional Name

(2R)-2-[(9E)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl octadecanoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C53H100O6/c1-4-7-10-13-16-19-22-25-26-29-31-34-37-40-43-46-52(55)58-49-50(59-53(56)47-44-41-38-35-32-28-24-21-18-15-12-9-6-3)48-57-51(54)45-42-39-36-33-30-27-23-20-17-14-11-8-5-2/h21,24,50H,4-20,22-23,25-49H2,1-3H3/b24-21+/t50-/m1/s1

InChI Key

YSNGWXHIKNKBNE-PZIDBCNXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

Alternative Parents

Substituents

Triacyl-sn-glycerol
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	10.69	ALOGPS
logP	19.45	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	51	ChemAxon
Refractivity	251.61 m³·mol⁻¹	ChemAxon
Polarizability	112.54 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

134782464

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for TG(16:0/16:1(9Z)/18:0)[iso6] (NP0334134)

MOL for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

3D MOL for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

3D SDF for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

3D-SDF for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

PDB for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

3D PDB for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

SMILES for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

INCHI for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

Structure for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])

3D Structure for NP0334134 (TG(16:0/16:1(9Z)/18:0)[iso6])