NP-MRD: Showing NP-Card for (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate (NP0215749)

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Record Information

Version

2.0

Created at

2022-09-05 15:28:05 UTC

Updated at

2022-09-05 15:28:05 UTC

NP-MRD ID

NP0215749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate

Description

CHEMBL247861 belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate is found in Lithospermum erythrorhizon. Based on a literature review very few articles have been published on CHEMBL247861.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217282D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052217282D          

 40 41  0  0  1  0            999 V2000
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    9.9408   -2.0171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2109   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0210   -1.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2910   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1012   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7510    0.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -2.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2910   -2.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8311   -3.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6413   -2.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5611   -3.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1012   -4.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9113   -4.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8311   -5.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0210   -5.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -4.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6708   -4.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7510   -4.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2109   -3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4007   -3.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
 27 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0215749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C/C\C=C/CCCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H46O6/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-31(38)40-30(23-20-25(2)3)26-24-29(37)32-27(35)21-22-28(36)33(32)34(26)39/h11-12,14-15,20-22,24,30,35-36H,4-10,13,16-19,23H2,1-3H3/b12-11-,15-14-/t30-/m1/s1

> <INCHI_KEY>
LRCJVQJYXQCXDX-PNURKKAPSA-N

> <FORMULA>
C34H46O6

> <MOLECULAR_WEIGHT>
550.736

> <EXACT_MASS>
550.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
64.09707778865732

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (6Z,9Z)-octadeca-6,9-dienoate

> <JCHEM_LOGP>
10.09798892366667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160495166115284

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489931525052603

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564946698481013

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
164.84680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6Z,9Z)-octadeca-6,9-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      17.044   8.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.540   6.712   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.028   6.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.524   4.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.011   4.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.507   3.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.995   2.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.491   1.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.979   1.182   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.475  -0.273   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.483  -1.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.979  -2.892   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.987  -4.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.499  -3.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.515  -2.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.524  -3.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.036  -2.892   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.540  -1.437   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      17.044  -4.056   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.556  -3.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.060  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.573  -2.019   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.077  -0.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.589  -0.273   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.068   0.600   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.564  -4.929   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.077  -4.638   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.085  -5.802   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      23.597  -5.511   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      21.581  -7.258   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.589  -8.422   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      24.101  -8.131   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      22.085  -9.877   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.573 -10.168   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.564  -9.004   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.052  -9.295   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      20.068  -7.549   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.060  -6.384   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      17.548  -6.675   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   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   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   28   39                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   38                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31   39                                                  
CONECT   39   38   27   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₆O₆

Average Mass

550.7360 Da

Monoisotopic Mass

550.32944 Da

IUPAC Name

(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (6Z,9Z)-octadeca-6,9-dienoate

Traditional Name

(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6Z,9Z)-octadeca-6,9-dienoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/C\C=C/CCCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C34H46O6/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-31(38)40-30(23-20-25(2)3)26-24-29(37)32-27(35)21-22-28(36)33(32)34(26)39/h11-12,14-15,20-22,24,30,35-36H,4-10,13,16-19,23H2,1-3H3/b12-11-,15-14-/t30-/m1/s1

InChI Key

LRCJVQJYXQCXDX-PNURKKAPSA-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
Lithospermum erythrorhizon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Naphthoquinone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Benzenoid
Vinylogous acid
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	10.1	ChemAxon
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-5.6	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	19	ChemAxon
Refractivity	164.85 m³·mol⁻¹	ChemAxon
Polarizability	64.1 Å³	ChemAxon
Number of Rings	2	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

23302767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44438574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate (NP0215749)

MOL for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

3D MOL for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

3D SDF for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

3D-SDF for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

PDB for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

3D PDB for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

SMILES for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

INCHI for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

Structure for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)

3D Structure for NP0215749 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (6z,9z)-octadeca-6,9-dienoate)