NP-MRD: Showing NP-Card for 2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+ (NP0026523)

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Record Information

Version

2.0

Created at

2021-06-19 18:22:33 UTC

Updated at

2021-06-29 23:52:06 UTC

NP-MRD ID

NP0026523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+

Provided By

JEOL Database JEOL Logo

Description

2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+ is found in Cystoseira crinita. 2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+ was first documented in 2003 (Fisch, K. M., et al.). Based on a literature review very few articles have been published on CHEMBL461274.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120223D          

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     RDKit          3D

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M  END


  Mrv1652306192120223D          

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M  END
> <DATABASE_ID>
NP0026523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C(O[H])C(=C1[H])C([H])([H])[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C(=O)C(\[H])=C(\C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-19(2)9-7-10-20(3)11-8-12-21(4)15-25(28)16-22(5)13-14-24-18-26(29)17-23(6)27(24)30/h9,11,13,15,17-18,29-30H,7-8,10,12,14,16H2,1-6H3/b20-11+,21-15-,22-13+

> <INCHI_KEY>
NESKDGGRNAMQOK-REACRFRISA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.598

> <EXACT_MASS>
410.282095084

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.89227597580039

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6Z,10E)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

> <ALOGPS_LOGP>
6.59

> <JCHEM_LOGP>
7.767773807333333

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.651162421506656

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.784983955658053

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5959514458485815

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
131.32969999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6Z,10E)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 68  0  0  0  0  0  0  0  0999 V2000
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 13 51  1  0
 13 52  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  3 34  1  0
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 30 68  1  0
 25 63  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.586   1.945  -1.429  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.539   0.462  -1.186  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.859  -0.133  -0.765  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.452  -0.323  -1.315  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.049   0.072  -1.700  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.029  -0.436  -0.669  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.435  -0.077  -0.880  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.317  -0.562   0.246  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.900   0.623  -1.935  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.329   1.025  -2.194  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.753   2.309  -1.464  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.944   3.537  -1.840  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.292   4.131  -3.182  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.983   4.107  -1.086  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.491   3.656   0.258  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.223   3.076   1.055  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.033   4.016   0.561  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.464   3.471   1.887  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.046   4.199   3.103  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.316   2.427   1.914  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.884   1.716   3.112  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.661   0.223   3.043  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.712  -0.607   2.623  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.541  -1.985   2.566  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.598  -2.738   2.145  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -2.572   2.932  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.267  -1.768   3.350  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.045  -2.390   3.736  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.436  -0.375   3.380  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.645   0.383   3.742  0.00  0.00           O+0
HETATM   31  H   UNK     0      -2.637   2.364  -1.768  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.333   2.176  -2.196  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.867   2.467  -0.508  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.792  -1.210  -0.579  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.211   0.341   0.157  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.611   0.024  -1.546  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.569  -1.390  -1.118  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.953   1.156  -1.800  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.831  -0.367  -2.681  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.102  -1.530  -0.613  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.322  -0.052   0.316  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.235  -1.649   0.347  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.374  -0.328   0.107  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.006  -0.101   1.189  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.209   0.961  -2.703  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.010   0.210  -1.922  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.458   1.149  -3.277  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.744   2.128  -0.387  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.808   2.509  -1.698  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.353   4.397  -3.216  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.719   5.040  -3.395  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.085   3.417  -3.985  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.444   4.969  -1.471  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.066   5.107   0.556  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.579   3.628  -0.264  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.110   3.999   3.258  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.087   5.279   2.979  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.481   3.926   4.021  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.637   1.999   0.963  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.474   2.081   4.059  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.960   1.927   3.158  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.671  -0.182   2.336  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.342  -3.674   2.182  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.211  -3.650   2.891  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.989  -3.483   3.724  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.829  -2.087   3.035  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.327  -2.086   4.749  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.632   1.200   3.211  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    5    2   37                                                  
CONECT    5    4    6   38   39                                             
CONECT    6    7    5   40   41                                             
CONECT    7    9    8    6                                                  
CONECT    8    7   42   43   44                                             
CONECT    9   10    7   45                                                  
CONECT   10    9   11   46   47                                             
CONECT   11   12   10   48   49                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   50   51   52                                             
CONECT   14   12   15   53                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18   15   54   55                                             
CONECT   18   20   17   19                                                  
CONECT   19   18   56   57   58                                             
CONECT   20   21   18   59                                                  
CONECT   21   22   20   60   61                                             
CONECT   22   21   29   23                                                  
CONECT   23   24   22   62                                                  
CONECT   24   26   23   25                                                  
CONECT   25   24   63                                                       
CONECT   26   27   24   64                                                  
CONECT   27   29   26   28                                                  
CONECT   28   27   65   66   67                                             
CONECT   29   22   27   30                                                  
CONECT   30   29   68                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   19                                                            
CONECT   57   19                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   21                                                            
CONECT   62   23                                                            
CONECT   63   25                                                            
CONECT   64   26                                                            
CONECT   65   28                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  136    0
END

RDKit          3D

68 68  0  0  0  0  0  0  0  0999 V2000
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 19 58  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₃

Average Mass

410.5980 Da

Monoisotopic Mass

410.28210 Da

IUPAC Name

(2E,6Z,10E)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

Traditional Name

(2E,6Z,10E)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C(O[H])C(=C1[H])C([H])([H])[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C(=O)C(\[H])=C(\C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H38O3/c1-19(2)9-7-10-20(3)11-8-12-21(4)15-25(28)16-22(5)13-14-24-18-26(29)17-23(6)27(24)30/h9,11,13,15,17-18,29-30H,7-8,10,12,14,16H2,1-6H3/b20-11+,21-15-,22-13+

InChI Key

NESKDGGRNAMQOK-REACRFRISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Carpodesmia crinita	JEOL database	Fisch, K. M., et al, J. Nat. Prod. 66, 968 (2003)

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
Prenylbenzoquinol
Hydroquinone
M-cresol
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	6.59	ALOGPS
logP	7.77	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	131.33 m³·mol⁻¹	ChemAxon
Polarizability	47.89 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

9287504

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11112370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fisch, K. M., et al. (2003). Fisch, K. M., et al, J. Nat. Prod. 66, 968 (2003). J. Nat. Prod..

Showing NP-Card for 2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+ (NP0026523)

MOL for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

3D MOL for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

3D SDF for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

3D-SDF for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

PDB for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

3D PDB for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

SMILES for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

INCHI for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

Structure for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)

3D Structure for NP0026523 (2-[(2'E,6'Z,10'E)-5'-oxo-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-+)