NP-MRD: Showing NP-Card for (8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione (NP0150533)

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Record Information

Version

2.0

Created at

2022-09-02 06:39:57 UTC

Updated at

2022-09-02 06:39:57 UTC

NP-MRD ID

NP0150533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione

Description

(7S,9R,1'S,2'S,3'S,4'R,5'R)-andicoquinone C 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 (7S,9R,1'S,2'S,3'S,4'R,5'R)-andicoquinone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208392D          

 37 41  0  0  1  0            999 V2000
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   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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M  END

     RDKit          3D

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M  END


  Mrv1652309022208392D          

 37 41  0  0  1  0            999 V2000
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 28 29  2  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0150533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H](OC2=CC=CC3=C2C(=O)C2=C(C=C4C[C@@](C)(O)C[C@H](O)C4=C2O)C3=O)O[C@H](C)[C@@H](O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O10/c1-11-23(32)27(3,34)24(35-4)25(36-11)37-16-7-5-6-13-18(16)22(31)19-14(20(13)29)8-12-9-26(2,33)10-15(28)17(12)21(19)30/h5-8,11,15,23-25,28,30,32-34H,9-10H2,1-4H3/t11-,15+,23-,24-,25+,26-,27+/m1/s1

> <INCHI_KEY>
ZNCXPUUERPXIAK-OSILDJSESA-N

> <FORMULA>
C27H30O10

> <MOLECULAR_WEIGHT>
514.527

> <EXACT_MASS>
514.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.82443838319117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,10S)-1-{[(2S,3S,4S,5R,6R)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.706627751

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.614979234190873

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.601342941390795

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8976054009453094

> <JCHEM_POLAR_SURFACE_AREA>
162.97999999999996

> <JCHEM_REFRACTIVITY>
130.36469999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,10S)-1-{[(2S,3S,4S,5R,6R)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.527   2.987   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.876  -3.026   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.153  -1.774   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   17                                                       
CONECT   28   15   10   29                                                  
CONECT   29   28                                                            
CONECT   30    4   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₀

Average Mass

514.5270 Da

Monoisotopic Mass

514.18390 Da

IUPAC Name

(8R,10S)-1-{[(2S,3S,4S,5R,6R)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

(8R,10S)-1-{[(2S,3S,4S,5R,6R)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](OC2=CC=CC3=C2C(=O)C2=C(C=C4C[C@@](C)(O)C[C@H](O)C4=C2O)C3=O)O[C@H](C)[C@@H](O)[C@]1(C)O

InChI Identifier

InChI=1S/C27H30O10/c1-11-23(32)27(3,34)24(35-4)25(36-11)37-16-7-5-6-13-18(16)22(31)19-14(20(13)29)8-12-9-26(2,33)10-15(28)17(12)21(19)30/h5-8,11,15,23-25,28,30,32-34H,9-10H2,1-4H3/t11-,15+,23-,24-,25+,26-,27+/m1/s1

InChI Key

ZNCXPUUERPXIAK-OSILDJSESA-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
Phenolic glycoside
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.29	ALOGPS
logP	1.71	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	130.36 m³·mol⁻¹	ChemAxon
Polarizability	52.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

71360637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione (NP0150533)

MOL for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0150533 ((8r,10s)-1-{[(2s,3s,4s,5r,6r)-4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl]oxy}-8,10,11-trihydroxy-8-methyl-9,10-dihydro-7h-tetracene-5,12-dione)