NP-MRD: Showing NP-Card for 10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione (NP0324181)

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Record Information

Version

2.0

Created at

2022-09-12 04:05:30 UTC

Updated at

2022-09-12 04:05:30 UTC

NP-MRD ID

NP0324181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione

Description

10-[(3,5-Dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. 10-[(3,5-Dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519132D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161519132D          

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    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 20 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 11 37  1  0  0  0  0
 17 37  1  0  0  0  0
  9 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(C)OC(OC2CC(C)(O)CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(OC)C(C)=CC=C2C4=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O11/c1-10-6-7-12-16(25(10)36-4)23(33)18-17(20(12)30)21(31)13-8-28(3,35)9-14(15(13)22(18)32)39-27-24(34)26(37-5)19(29)11(2)38-27/h6-7,11,14,19,24,26-27,29,31-32,34-35H,8-9H2,1-5H3

> <INCHI_KEY>
FYHKGQZAUWDZBL-UHFFFAOYSA-N

> <FORMULA>
C28H32O11

> <MOLECULAR_WEIGHT>
544.553

> <EXACT_MASS>
544.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.95206350420496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.9290336540000004

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.116277224838118

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.236336388618078

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9187186833995975

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
137.49979999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7H-tetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.484  -5.657   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.474  -3.943   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   38                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   23   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   20   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   11   17                                                  
CONECT   38    9    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₁

Average Mass

544.5530 Da

Monoisotopic Mass

544.19446 Da

IUPAC Name

10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

COC1C(O)C(C)OC(OC2CC(C)(O)CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(OC)C(C)=CC=C2C4=O)C1O

InChI Identifier

InChI=1S/C28H32O11/c1-10-6-7-12-16(25(10)36-4)23(33)18-17(20(12)30)21(31)13-8-28(3,35)9-14(15(13)22(18)32)39-27-24(34)26(37-5)19(29)11(2)38-27/h6-7,11,14,19,24,26-27,29,31-32,34-35H,8-9H2,1-5H3

InChI Key

FYHKGQZAUWDZBL-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Anisole
Alkyl aryl ether
Oxane
Benzenoid
Monosaccharide
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Ketone
Ether
Dialkyl ether
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	2.07	ALOGPS
logP	2.93	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.5 m³·mol⁻¹	ChemAxon
Polarizability	56.95 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione (NP0324181)

MOL for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0324181 (10-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-1-methoxy-2,8-dimethyl-9,10-dihydro-7h-tetracene-5,12-dione)