NP-MRD: Showing NP-Card for 6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione (NP0239733)

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Record Information

Version

2.0

Created at

2022-09-06 23:23:16 UTC

Updated at

2022-09-06 23:23:16 UTC

NP-MRD ID

NP0239733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione

Description

3-Deoxyrabelomycin belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. 6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione is found in Streptomyces griseoincarnatus. Based on a literature review very few articles have been published on 3-Deoxyrabelomycin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    5.1544    0.7814   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6494    0.7113   -0.7939 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2022   -0.7175   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847   -1.0146   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632   -2.1383    0.2848 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    0.0719    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    1.3448    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    2.3648    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    2.1290    0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926    3.2119    1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    0.9107    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -0.1422    0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4467   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155   -2.3982   -0.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -1.6306   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649   -2.8689   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310   -3.0796   -0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073   -2.0891   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -0.8210    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4353    0.1444    0.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -0.6297    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.6954    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3600    1.6798    0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    1.4464    0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5553    1.5589   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5420    1.0857    0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6299   -0.1812   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113    1.2352   -1.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -0.9321   -1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645   -1.3563   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    3.3455    0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1322    4.1070    1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890   -3.6532   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5087   -4.0682   -0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0994   -2.2583   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4206    1.0686    0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    1.0101    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    2.5229    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7 24  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 24  2  1  0
 22 11  1  0
 12  6  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  6
  3 29  1  0
  3 30  1  0
 24 37  1  0
 24 38  1  0
  8 31  1  0
 10 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END


  Mrv1652309072201232D          

 24 27  0  0  0  0            999 V2000
    6.1154    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    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
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 24  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(=O)C2=C(C1)C=C(O)C1=C2C(=O)C2=CC=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O5/c1-8-5-9-7-13(22)16-17(14(9)12(21)6-8)18(23)10-3-2-4-11(20)15(10)19(16)24/h2-4,7-8,20,22H,5-6H2,1H3

> <INCHI_KEY>
OTYDQANROURYGR-UHFFFAOYSA-N

> <FORMULA>
C19H14O5

> <MOLECULAR_WEIGHT>
322.316

> <EXACT_MASS>
322.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.97254950855249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <JCHEM_LOGP>
4.206473379999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8561061914875285

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.532045718094274

> <JCHEM_PKA_STRONGEST_BASIC>
-6.04693426434454

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
87.9301

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.415   0.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.375  -1.558   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.870   3.971   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.366   5.427   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21   11   23                                                  
CONECT   23   22                                                            
CONECT   24    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₅

Average Mass

322.3160 Da

Monoisotopic Mass

322.08412 Da

IUPAC Name

6,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

6,8-dihydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C2=C(C1)C=C(O)C1=C2C(=O)C2=CC=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C19H14O5/c1-8-5-9-7-13(22)16-17(14(9)12(21)6-8)18(23)10-3-2-4-11(20)15(10)19(16)24/h2-4,7-8,20,22H,5-6H2,1H3

InChI Key

OTYDQANROURYGR-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 griseoincarnatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenanthrol
Anthracene
Phenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	4.21	ChemAxon
pKa (Strongest Acidic)	6.53	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.93 m³·mol⁻¹	ChemAxon
Polarizability	32.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

15660371

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione (NP0239733)

MOL for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D MOL for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D SDF for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D-SDF for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

PDB for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D PDB for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

SMILES for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

INCHI for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

Structure for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D Structure for NP0239733 (6,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)