NP-MRD: Showing NP-Card for 10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0178726)

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Record Information

Version

2.0

Created at

2022-09-03 16:46:34 UTC

Updated at

2022-09-03 16:46:34 UTC

NP-MRD ID

NP0178726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

10-{[4-(Dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. 10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione is found in Streptomyces purpurascens. 10-{[4-(Dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161515372D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161515372D          

 39 43  0  0  0  0            999 V2000
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    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 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  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 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
 22 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
 19 37  1  0  0  0  0
 37 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(O)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1O)C(=O)C1=CC=CC(O)=C1C3=O

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

> <INCHI_KEY>
HINUXGZHCXYZMB-UHFFFAOYSA-N

> <FORMULA>
C28H33NO10

> <MOLECULAR_WEIGHT>
543.569

> <EXACT_MASS>
543.210446267

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.882473248638775

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.554938347021608

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.231302838163328

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.721352938512411

> <JCHEM_PKA_STRONGEST_BASIC>
8.725311989010223

> <JCHEM_POLAR_SURFACE_AREA>
177.22

> <JCHEM_REFRACTIVITY>
139.17269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-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  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -7.700   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       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   38                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    6   20   37                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   34                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   22   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   19   38                                                  
CONECT   38   37    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

C₂₈H₃₃NO₁₀

Average Mass

543.5690 Da

Monoisotopic Mass

543.21045 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCC1(O)CC(OC2CC(C(O)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1O)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

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

InChI Key

HINUXGZHCXYZMB-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 purpurascens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	2.04	ALOGPS
logP	2.55	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	8.73	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	139.17 m³·mol⁻¹	ChemAxon
Polarizability	56.88 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

14253283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0178726)

MOL for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0178726 (10-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-1,6,7,8,11-pentahydroxy-9,10-dihydro-7h-tetracene-5,12-dione)