NP-MRD: Showing NP-Card for 6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione (NP0222291)

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Record Information

Version

2.0

Created at

2022-09-06 00:05:28 UTC

Updated at

2022-09-06 00:05:28 UTC

NP-MRD ID

NP0222291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione

Description

Cordiaquinone H belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione is found in Varronia linnaei. Based on a literature review very few articles have been published on Cordiaquinone H.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202052D          

 25 27  0  0  1  0            999 V2000
   -2.9078   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1196   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4570    1.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452    0.7284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3600    1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    0.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1164    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1652309062202052D          

 25 27  0  0  1  0            999 V2000
   -2.9078   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1196   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4570    1.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452    0.7284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3600    1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    0.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1164    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H](O)[C@@](C)(O)[C@@]1(C)CCC1=CC=C2C(=O)C=CC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O4/c1-13-4-9-19(24)21(3,25)20(13,2)11-10-14-5-6-15-16(12-14)18(23)8-7-17(15)22/h5-8,12-13,19,24-25H,4,9-11H2,1-3H3/t13-,19-,20+,21-/m1/s1

> <INCHI_KEY>
NJQYJWPUYFYJJK-NHDXWUKRSA-N

> <FORMULA>
C21H26O4

> <MOLECULAR_WEIGHT>
342.435

> <EXACT_MASS>
342.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.89582249542816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{2-[(1S,2S,3R,6R)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}-1,4-dihydronaphthalene-1,4-dione

> <JCHEM_LOGP>
3.060372734333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.530541281651164

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.412556079272932

> <JCHEM_PKA_STRONGEST_BASIC>
-3.238373422911846

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
98.11569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-{2-[(1S,2S,3R,6R)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.428  -2.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.151  -1.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.690  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.413   0.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.597   1.413   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.320   2.773   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.058   1.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.272   2.885   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.593   1.836   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.951   0.675   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₄

Average Mass

342.4350 Da

Monoisotopic Mass

342.18311 Da

IUPAC Name

6-{2-[(1S,2S,3R,6R)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}-1,4-dihydronaphthalene-1,4-dione

Traditional Name

6-{2-[(1S,2S,3R,6R)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H](O)[C@@](C)(O)[C@@]1(C)CCC1=CC=C2C(=O)C=CC(=O)C2=C1

InChI Identifier

InChI=1S/C21H26O4/c1-13-4-9-19(24)21(3,25)20(13,2)11-10-14-5-6-15-16(12-14)18(23)8-7-17(15)22/h5-8,12-13,19,24-25H,4,9-11H2,1-3H3/t13-,19-,20+,21-/m1/s1

InChI Key

NJQYJWPUYFYJJK-NHDXWUKRSA-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
Cordia linnaei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Cyclohexanol
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.06	ChemAxon
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.12 m³·mol⁻¹	ChemAxon
Polarizability	37.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8264295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10088758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione (NP0222291)

MOL for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

3D MOL for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

3D SDF for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

3D-SDF for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

PDB for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

3D PDB for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

SMILES for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

INCHI for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

Structure for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)

3D Structure for NP0222291 (6-{2-[(1s,2s,3r,6r)-2,3-dihydroxy-1,2,6-trimethylcyclohexyl]ethyl}naphthalene-1,4-dione)