NP-MRD: Showing NP-Card for Ardisiaquinone I (NP0075106)

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Record Information

Version

2.0

Created at

2022-04-28 20:24:59 UTC

Updated at

2022-04-28 20:24:59 UTC

NP-MRD ID

NP0075106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ardisiaquinone I

Description

2-{15-[5-(Acetyloxy)-2-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Ardisiaquinone I is found in Ardisia teysmanniana Scheff. 2-{15-[5-(Acetyloxy)-2-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507072D          

 43 44  0  0  0  0            999 V2000
    3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5 41  1  0  0  0  0
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 10 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251507072D          

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    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 40  1  0  0  0  0
 11 41  1  0  0  0  0
  5 41  1  0  0  0  0
 41 42  2  0  0  0  0
 10 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=C(C)C(=O)C(O)=C(CCCCCCCCCCCCCCCC2=C(OC(C)=O)C(=O)C(C)=C(O)C2=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O10/c1-20-26(36)30(40)25(33(28(20)38)43-23(4)35)19-17-15-13-11-9-7-5-6-8-10-12-14-16-18-24-29(39)27(37)21(2)32(31(24)41)42-22(3)34/h36,39H,5-19H2,1-4H3

> <INCHI_KEY>
DKFZOIQHKSWVRR-UHFFFAOYSA-N

> <FORMULA>
C33H44O10

> <MOLECULAR_WEIGHT>
600.705

> <EXACT_MASS>
600.293447617

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
67.39334031085059

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{15-[2-(acetyloxy)-5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
6.6931181890000015

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.777988598473479

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.175452207086164

> <JCHEM_PKA_STRONGEST_BASIC>
-5.326450382481416

> <JCHEM_POLAR_SURFACE_AREA>
161.34

> <JCHEM_REFRACTIVITY>
163.66940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{15-[2-(acetyloxy)-5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335 -23.100   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.002 -23.100   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.006 -18.480   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.340 -19.250   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.341 -18.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.675 -19.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.008 -18.480   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      32.008 -16.940   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      33.342 -16.170   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      33.342 -14.630   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      34.676 -16.940   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.342 -19.250   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      34.676 -18.480   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      33.342 -20.790   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      32.008 -21.560   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      32.008 -23.100   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      30.675 -20.790   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      29.341 -21.560   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      34.676 -21.560   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669 -21.560   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   41                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   43                                                  
CONECT   11   10   12   41                                                  
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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   38                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   27   39                                                  
CONECT   39   38                                                            
CONECT   40   35                                                            
CONECT   41   11    5   42                                                  
CONECT   42   41                                                            
CONECT   43   10                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

View in JSmol

Synonyms

Value	Source
2-{15-[5-(acetyloxy)-2-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₀

Average Mass

600.7050 Da

Monoisotopic Mass

600.29345 Da

IUPAC Name

5-{15-[2-(acetyloxy)-5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

Traditional Name

5-{15-[2-(acetyloxy)-5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]pentadecyl}-4-hydroxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=C(C)C(=O)C(O)=C(CCCCCCCCCCCCCCCC2=C(OC(C)=O)C(=O)C(C)=C(O)C2=O)C1=O

InChI Identifier

InChI=1S/C33H44O10/c1-20-26(36)30(40)25(33(28(20)38)43-23(4)35)19-17-15-13-11-9-7-5-6-8-10-12-14-16-18-24-29(39)27(37)21(2)32(31(24)41)42-22(3)34/h36,39H,5-19H2,1-4H3

InChI Key

DKFZOIQHKSWVRR-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ardisia teysmanniana Scheff.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Dicarboxylic acid or derivatives
Vinylogous acid
Enol ester
Carboxylic acid ester
Enol
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	ALOGPS
logP	6.69	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	5.18	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	161.34 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	163.67 m³·mol⁻¹	ChemAxon
Polarizability	67.39 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

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

10438557

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ardisiaquinone I (NP0075106)

MOL for NP0075106 (Ardisiaquinone I)

3D MOL for NP0075106 (Ardisiaquinone I)

3D SDF for NP0075106 (Ardisiaquinone I)

3D-SDF for NP0075106 (Ardisiaquinone I)

PDB for NP0075106 (Ardisiaquinone I)

3D PDB for NP0075106 (Ardisiaquinone I)

SMILES for NP0075106 (Ardisiaquinone I)

INCHI for NP0075106 (Ardisiaquinone I)

Structure for NP0075106 (Ardisiaquinone I)

3D Structure for NP0075106 (Ardisiaquinone I)