NP-MRD: Showing NP-Card for 2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione (NP0141392)

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Record Information

Version

2.0

Created at

2022-09-01 19:42:37 UTC

Updated at

2022-09-01 19:42:38 UTC

NP-MRD ID

NP0141392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione

Description

2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-13-yl]-1,6,10-trihydroxy-8-methyl-5,12-dihydrotetracene-5,12-dione belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. Based on a literature review very few articles have been published on 2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-13-yl]-1,6,10-trihydroxy-8-methyl-5,12-dihydrotetracene-5,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012221422D          

 41 47  0  0  1  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309012221422D          

 41 47  0  0  1  0            999 V2000
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   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.1434    2.0625    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  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  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 20 36  1  0  0  0  0
 19 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 16 39  1  0  0  0  0
 39 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0141392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](C[C@H]2OC3O[C@H](C)C(=O)CC3O[C@H]12)C1=CC=C2C(=O)C3=C(O)C4=CC(C)=CC(O)=C4C=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O10/c1-11-6-17-16(20(33)7-11)8-18-25(28(17)36)27(35)15-5-4-14(26(34)24(15)29(18)37)21-10-22-30(13(3)38-21)40-23-9-19(32)12(2)39-31(23)41-22/h4-8,12-13,21-23,30-31,33-34,36H,9-10H2,1-3H3/t12-,13-,21+,22-,23?,30-,31?/m1/s1

> <INCHI_KEY>
FNLPBRGKEZDCNF-MEAGLVDUSA-N

> <FORMULA>
C31H28O10

> <MOLECULAR_WEIGHT>
560.555

> <EXACT_MASS>
560.168247102

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
58.0595957662217

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyl-5,12-dihydrotetracene-5,12-dione

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
5.558904526666667

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.058957182110351

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.458887413747722

> <JCHEM_PKA_STRONGEST_BASIC>
-3.70069843676418

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
144.31719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   40                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   39                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   37                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   22   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   20                                                       
CONECT   37   19   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   16   40                                                  
CONECT   40   39    8   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₈O₁₀

Average Mass

560.5550 Da

Monoisotopic Mass

560.16825 Da

IUPAC Name

2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyl-5,12-dihydrotetracene-5,12-dione

Traditional Name

2-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](C[C@H]2OC3O[C@H](C)C(=O)CC3O[C@H]12)C1=CC=C2C(=O)C3=C(O)C4=CC(C)=CC(O)=C4C=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C31H28O10/c1-11-6-17-16(20(33)7-11)8-18-25(28(17)36)27(35)15-5-4-14(26(34)24(15)29(18)37)21-10-22-30(13(3)38-21)40-23-9-19(32)12(2)39-31(23)41-22/h4-8,12-13,21-23,30-31,33-34,36H,9-10H2,1-3H3/t12-,13-,21+,22-,23?,30-,31?/m1/s1

InChI Key

FNLPBRGKEZDCNF-MEAGLVDUSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
1,4-anthraquinone
9,10-anthraquinone
1-naphthol
Pyranodioxin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Para-dioxane
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.59	ALOGPS
logP	5.56	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	144.32 m³·mol⁻¹	ChemAxon
Polarizability	58.06 Å³	ChemAxon
Number of Rings	7	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

163108668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione (NP0141392)

MOL for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

3D MOL for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

3D SDF for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

3D-SDF for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

PDB for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

3D PDB for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

SMILES for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

INCHI for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

Structure for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)

3D Structure for NP0141392 (2-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,6,10-trihydroxy-8-methyltetracene-5,12-dione)