NP-MRD: Showing NP-Card for 16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid (NP0180593)

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Record Information

Version

2.0

Created at

2022-09-03 18:58:45 UTC

Updated at

2022-09-03 18:58:45 UTC

NP-MRD ID

NP0180593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid

Description

16-[(4-Methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. 16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid is found in Boletinus cavipes. Based on a literature review very few articles have been published on 16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220582D          

 32 31  0  0  0  0            999 V2000
   13.2000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2375   -0.7145    0.0000 O   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


  Mrv1652309032220582D          

 32 31  0  0  0  0            999 V2000
   13.2000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0180593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C=C(C)C(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O6/c1-19(10-7-11-20(2)14-9-15-22(4)25(28)29)12-8-13-21(3)16-17-32-26(30)23(5)18-24(27)31-6/h11-12,15-16,18H,7-10,13-14,17H2,1-6H3,(H,28,29)

> <INCHI_KEY>
RSIAIWLXCCYWMC-UHFFFAOYSA-N

> <FORMULA>
C26H38O6

> <MOLECULAR_WEIGHT>
446.584

> <EXACT_MASS>
446.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.57643425643795

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid

> <JCHEM_LOGP>
6.645172450333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.071157682967406

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565487617157034

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
130.7455

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      24.640   8.002   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      23.100   8.002   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      22.330   9.336   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      23.100  10.669   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      20.790   9.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.020  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.710  12.003   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.710   9.336   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.090   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Value	Source
16-[(4-Methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoate	Generator

Chemical Formula

C₂₆H₃₈O₆

Average Mass

446.5840 Da

Monoisotopic Mass

446.26684 Da

IUPAC Name

16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid

Traditional Name

16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C=C(C)C(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C(O)=O

InChI Identifier

InChI=1S/C26H38O6/c1-19(10-7-11-20(2)14-9-15-22(4)25(28)29)12-8-13-21(3)16-17-32-26(30)23(5)18-24(27)31-6/h11-12,15-16,18H,7-10,13-14,17H2,1-6H3,(H,28,29)

InChI Key

RSIAIWLXCCYWMC-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
Boletinus cavipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen 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	6.65	ChemAxon
pKa (Strongest Acidic)	5.07	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	130.75 m³·mol⁻¹	ChemAxon
Polarizability	52.58 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

162874780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid (NP0180593)

MOL for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

3D MOL for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

3D SDF for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

3D-SDF for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

PDB for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

3D PDB for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

SMILES for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

INCHI for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

Structure for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)

3D Structure for NP0180593 (16-[(4-methoxy-2-methyl-4-oxobut-2-enoyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid)