NP-MRD: Showing NP-Card for 7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0231260)

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Record Information

Version

2.0

Created at

2022-09-06 12:02:07 UTC

Updated at

2022-09-06 12:02:07 UTC

NP-MRD ID

NP0231260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione

Description

Obelmycin G 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. 7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione is found in Streptomyces violaceus. Obelmycin G is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514402D          

 39 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161514402D          

 39 43  0  0  0  0            999 V2000
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    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  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  1  0  0  0  0
 18 20  2  0  0  0  0
 13 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
 10 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CCC2=C(O)C3=C(C(O)=C2C1OC1CC(C(O)C(C)O1)N(C)C)C(=O)C1=C(O)C=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO10/c1-5-28(37)9-8-12-17(27(28)39-16-10-13(29(3)4)22(32)11(2)38-16)24(34)21-20(23(12)33)25(35)18-14(30)6-7-15(31)19(18)26(21)36/h6-7,11,13,16,22,27,30-34,37H,5,8-10H2,1-4H3

> <INCHI_KEY>
AUMGNUSJWBCZIZ-UHFFFAOYSA-N

> <FORMULA>
C28H33NO10

> <MOLECULAR_WEIGHT>
543.569

> <EXACT_MASS>
543.210446267

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.30037185935687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
4.322864827214701

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.8389851098761

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.873392549032143

> <JCHEM_PKA_STRONGEST_BASIC>
8.363029807143594

> <JCHEM_POLAR_SURFACE_AREA>
177.21999999999997

> <JCHEM_REFRACTIVITY>
139.68169999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-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       1.958  -5.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.484  -6.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.474  -8.377   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   37  N   UNK     0       2.667 -13.860   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   27                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   10   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   27                                                  
CONECT   27   26    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   31   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃NO₁₀

Average Mass

543.5690 Da

Monoisotopic Mass

543.21045 Da

IUPAC Name

7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

CCC1(O)CCC2=C(O)C3=C(C(O)=C2C1OC1CC(C(O)C(C)O1)N(C)C)C(=O)C1=C(O)C=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C28H33NO10/c1-5-28(37)9-8-12-17(27(28)39-16-10-13(29(3)4)22(32)11(2)38-16)24(34)21-20(23(12)33)25(35)18-14(30)6-7-15(31)19(18)26(21)36/h6-7,11,13,16,22,27,30-34,37H,5,8-10H2,1-4H3

InChI Key

AUMGNUSJWBCZIZ-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
Streptomyces violaceus	LOTUS Database	35616633

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
Aminoglycoside core
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
1,2-aminoalcohol
Tertiary amine
Secondary alcohol
Ketone
Tertiary aliphatic amine
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Amine
Organooxygen compound
Organonitrogen compound
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	2.13	ALOGPS
logP	4.32	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	177.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.68 m³·mol⁻¹	ChemAxon
Polarizability	55.3 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

176063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0231260)

MOL for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0231260 (7-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)