NP-MRD: Showing NP-Card for 3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione (NP0274663)

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Record Information

Version

2.0

Created at

2022-09-08 22:08:14 UTC

Updated at

2022-09-08 22:08:14 UTC

NP-MRD ID

NP0274663

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione

Description

Lanciaquinone 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. 3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione is found in Maesa lanceolata. 3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione was first documented in 2003 (PMID: 14559281). Based on a literature review very few articles have been published on Lanciaquinone (PMID: 18785746).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092200082D          

 34 35  0  0  0  0            999 V2000
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    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  2  0  0  0  0
  8 33  2  0  0  0  0
  2 33  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092200082D          

 34 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0274663

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C(=O)C(CCCCCCCCCCCCCCC2=C(O)C(=O)C=C(O)C2=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O7/c1-18-16-21(28)25(32)19(24(18)31)14-12-10-8-6-4-2-3-5-7-9-11-13-15-20-26(33)22(29)17-23(30)27(20)34/h16-17,29,31,34H,2-15H2,1H3

> <INCHI_KEY>
LRSQFPDKYLRQEO-UHFFFAOYSA-N

> <FORMULA>
C27H36O7

> <MOLECULAR_WEIGHT>
472.578

> <EXACT_MASS>
472.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.78258832743686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione

> <JCHEM_LOGP>
6.550004123999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.677772137649519

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.075316812120045

> <JCHEM_PKA_STRONGEST_BASIC>
-5.244106641108563

> <JCHEM_POLAR_SURFACE_AREA>
128.97

> <JCHEM_REFRACTIVITY>
134.44089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.674 -16.940   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.007 -16.170   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.007 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      29.341 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      30.675 -16.170   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      29.341 -18.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      28.007 -20.790   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.340 -19.250   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23   32                                                  
CONECT   32   31                                                            
CONECT   33    8    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₇

Average Mass

472.5780 Da

Monoisotopic Mass

472.24610 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C(=O)C(CCCCCCCCCCCCCCC2=C(O)C(=O)C=C(O)C2=O)=C1O

InChI Identifier

InChI=1S/C27H36O7/c1-18-16-21(28)25(32)19(24(18)31)14-12-10-8-6-4-2-3-5-7-9-11-13-15-20-26(33)22(29)17-23(30)27(20)34/h16-17,29,31,34H,2-15H2,1H3

InChI Key

LRSQFPDKYLRQEO-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, 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
Maesa lanceolata	LOTUS Database	35616633

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
O-benzoquinone
Vinylogous acid
Enol
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

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

101762594

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guillonneau L, Taddei D, Moody CJ: Synthesis of the reported structure of the bisbenzoquinone lanciaquinone, isolated from Maesa lanceolata. Org Lett. 2008 Oct 16;10(20):4505-8. doi: 10.1021/ol801697g. Epub 2008 Sep 12. [PubMed:18785746 ]
Arot Manguro LO, Midiwo JO, Kraus W, Ugi I: Benzoquinone derivatives of Myrsine africana and Maesa lanceolata. Phytochemistry. 2003 Oct;64(4):855-62. doi: 10.1016/s0031-9422(03)00428-x. [PubMed:14559281 ]
LOTUS database [Link]

Showing NP-Card for 3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione (NP0274663)

MOL for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

3D MOL for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

3D SDF for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

3D-SDF for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

PDB for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

3D PDB for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

SMILES for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

INCHI for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

Structure for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)

3D Structure for NP0274663 (3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-4-hydroxy-5-methylcyclohexa-3,5-diene-1,2-dione)