NP-MRD: Showing NP-Card for 3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione (NP0198652)

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Record Information

Version

1.0

Created at

2022-09-04 17:08:19 UTC

Updated at

2022-09-04 17:08:20 UTC

NP-MRD ID

NP0198652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

Description

Ardisiaquinone E belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione is found in Ardisia sieboldii. It was first documented in 1995 (PMID: 7553985). Based on a literature review very few articles have been published on Ardisiaquinone E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219082D          

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M  END

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  Mrv1652309042219082D          

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 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 26 33  1  0  0  0  0
  9 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0198652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(O)=C(CCCCCCC\C=C/CCCCCCCC2=CC(O)=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-35-27-21-26(32)28(33)25(29(27)34)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22-18-23(30)20-24(31)19-22/h2-3,18-21,30-31,33H,4-17H2,1H3/b3-2-

> <INCHI_KEY>
UAVAYCHSCHCWEM-IHWYPQMZSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.77292797881271

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(8Z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

> <JCHEM_LOGP>
7.773026640000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.35912983959741

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.72446129943676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.944394782173224

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
142.8613

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(8Z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
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                                                       
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   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26                                                       
CONECT   34    9    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

3-[(8Z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

3-[(8Z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(O)=C(CCCCCCC\C=C/CCCCCCCC2=CC(O)=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C29H40O6/c1-35-27-21-26(32)28(33)25(29(27)34)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22-18-23(30)20-24(31)19-22/h2-3,18-21,30-31,33H,4-17H2,1H3/b3-2-

InChI Key

UAVAYCHSCHCWEM-IHWYPQMZSA-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
Ardisia sieboldii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

P-benzoquinone
Quinone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Vinylogous ester
Vinylogous acid
Ketone
Cyclic ketone
Enol
Organic oxide
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen 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	7.77	ChemAxon
pKa (Strongest Acidic)	5.72	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	142.86 m³·mol⁻¹	ChemAxon
Polarizability	56.77 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

C00036746

Chemspider ID

8498545

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10323081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fukuyama Y, Kiriyama Y, Kodama M, Iwaki H, Hosozawa S, Aki S, Matsui K: Naturally occurring 5-lipoxygenase inhibitors. VI. Structures of ardisiaquinones D, E, and F from Ardisia sieboldii. Chem Pharm Bull (Tokyo). 1995 Aug;43(8):1391-4. doi: 10.1248/cpb.43.1391. [PubMed:7553985 ]
LOTUS database [Link]

Showing NP-Card for 3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione (NP0198652)

MOL for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

PDB for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

SMILES for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

INCHI for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

Structure for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0198652 (3-[(8z)-16-(3,5-dihydroxyphenyl)hexadec-8-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)