NP-MRD: Showing NP-Card for methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate (NP0293780)

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Record Information

Version

2.0

Created at

2022-09-10 01:59:05 UTC

Updated at

2022-09-10 01:59:05 UTC

NP-MRD ID

NP0293780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate

Description

CHEMBL490781 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate is found in Sargassum siliquastrum. Based on a literature review very few articles have been published on CHEMBL490781.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102203592D          

 34 34  0  0  1  0            999 V2000
    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6566    3.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 74 74  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309102203592D          

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  5 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0293780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)[C@@H](O)[C@@H](O)C=C(C)C)CC(=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c1-19(2)17-24(30)26(32)22(5)12-8-11-20(3)9-7-10-21(4)15-16-28(27(33)34-6)18-23(29)13-14-25(28)31/h9,12-15,17,24,26,30,32H,7-8,10-11,16,18H2,1-6H3/b20-9+,21-15+,22-12+/t24-,26+,28?/m0/s1

> <INCHI_KEY>
JRWWQINKMAMEOS-BEMIFWKESA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.27841926416321

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1-[(2E,6E,10E,12R,13S)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate

> <JCHEM_LOGP>
5.147613631666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.58802885921245

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.347809439658914

> <JCHEM_PKA_STRONGEST_BASIC>
-3.337998625169279

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
138.853

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-[(2E,6E,10E,12R,13S)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.797   4.937   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173   3.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.163   4.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.636   5.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.679   4.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.669   5.314   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.186   5.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.176   6.227   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.649   7.674   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.692   5.959   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.682   7.139   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -11.199   6.871   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.189   8.051   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.662   9.498   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.705   7.784   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -14.232   6.337   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -14.695   8.963   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -14.168  10.411   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -16.212   8.696   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -17.202   9.876   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -18.718   9.608   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.675  11.323   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334   2.310   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   28   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

methyl 1-[(2E,6E,10E,12R,13S)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate

Traditional Name

methyl 1-[(2E,6E,10E,12R,13S)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)[C@@H](O)[C@@H](O)C=C(C)C)CC(=O)C=CC1=O

InChI Identifier

InChI=1S/C28H40O6/c1-19(2)17-24(30)26(32)22(5)12-8-11-20(3)9-7-10-21(4)15-16-28(27(33)34-6)18-23(29)13-14-25(28)31/h9,12-15,17,24,26,30,32H,7-8,10-11,16,18H2,1-6H3/b20-9+,21-15+,22-12+/t24-,26+,28?/m0/s1

InChI Key

JRWWQINKMAMEOS-BEMIFWKESA-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
Sargassum siliquastrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Long chain fatty alcohol
Prenylbenzoquinone
Fatty alcohol
Fatty acid ester
Cyclohexenone
Fatty acyl
Methyl ester
1,2-diol
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	5.15	ChemAxon
pKa (Strongest Acidic)	13.35	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	138.85 m³·mol⁻¹	ChemAxon
Polarizability	53.28 Å³	ChemAxon
Number of Rings	1	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

24704800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44579813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate (NP0293780)

MOL for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

3D MOL for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

3D SDF for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

3D-SDF for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

PDB for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

3D PDB for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

SMILES for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

INCHI for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

Structure for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)

3D Structure for NP0293780 (methyl 1-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dioxocyclohex-3-ene-1-carboxylate)