NP-MRD: Showing NP-Card for ochromycinone (NP0179726)

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Record Information

Version

2.0

Created at

2022-09-03 17:57:32 UTC

Updated at

2022-09-03 17:57:32 UTC

NP-MRD ID

NP0179726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ochromycinone

Description

Ochromycinone 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. It was first documented in 2007 (PMID: 17625884). Based on a literature review a significant number of articles have been published on Ochromycinone (PMID: 18081255) (PMID: 23549355) (PMID: 23215652) (PMID: 21299120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.1859    0.3632    1.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297   -0.4455    0.0454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0482   -1.5870    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -1.5529   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154   -2.5813   -0.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1160   -0.2516   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666    0.7765   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4360    1.9809   -1.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0621    2.2164   -1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7545    1.2079   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2356   -0.0552   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980   -1.1036    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -2.2185    0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311   -0.8603    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3211   -1.8870    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -1.7110    0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2557   -0.5073    0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403    0.5410    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0274    1.7104   -0.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    0.3696   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1962    1.4320   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6511    2.5627   -0.8330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    0.4915   -0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0556   -0.2474    2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1959    0.8166    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869    1.1569    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143   -0.8215   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9845   -1.6993    1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369   -2.5347    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513    2.8154   -1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397    3.1818   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -2.8441    1.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288   -2.5063    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3036   -0.2945    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7732    2.5720   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9347    1.4562   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5816    0.0581   -2.0111 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 23  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 23  2  1  0
 21 10  1  0
 11  6  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
 23 36  1  0
 23 37  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
M  END


  Mrv1652309032219572D          

 23 26  0  0  1  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  2  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
    2.6048    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
  2  1  1  6  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
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 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
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC(=O)C2=C(C1)C=CC1=C2C(=O)C2=CC=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-6,9,20H,7-8H2,1H3/t9-/m0/s1

> <INCHI_KEY>
ZAWXOCUFQSQDJS-VIFPVBQESA-N

> <FORMULA>
C19H14O4

> <MOLECULAR_WEIGHT>
306.317

> <EXACT_MASS>
306.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.764676907896956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-8-hydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <JCHEM_LOGP>
3.8600387016666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.524095321767337

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.823064350404852

> <JCHEM_PKA_STRONGEST_BASIC>
-6.044701994278991

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
85.94919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-8-hydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   10   22                                                  
CONECT   22   21                                                            
CONECT   23    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₄

Average Mass

306.3170 Da

Monoisotopic Mass

306.08921 Da

IUPAC Name

(3S)-8-hydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

(3S)-8-hydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC(=O)C2=C(C1)C=CC1=C2C(=O)C2=CC=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C19H14O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-6,9,20H,7-8H2,1H3/t9-/m0/s1

InChI Key

ZAWXOCUFQSQDJS-VIFPVBQESA-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 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
Anthracene
Phenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
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	3.86	ChemAxon
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.95 m³·mol⁻¹	ChemAxon
Polarizability	31.76 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

9983594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11808929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fotso S, Mahmud T, Zabriskie TM, Santosa DA, Sulastri, Proteau PJ: Angucyclinones from an Indonesian Streptomyces sp. J Nat Prod. 2008 Jan;71(1):61-5. doi: 10.1021/np0704102. Epub 2007 Dec 15. [PubMed:18081255 ]
Boonlarppradab C, Suriyachadkun C, Rachtawee P, Choowong W: Saccharosporones A, B and C, cytotoxic antimalarial angucyclinones from Saccharopolyspora sp. BCC 21906. J Antibiot (Tokyo). 2013 Jun;66(6):305-9. doi: 10.1038/ja.2013.16. Epub 2013 Apr 3. [PubMed:23549355 ]
Kaliappan KP, Ravikumar V: Angucyclinone antibiotics: total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755. J Org Chem. 2007 Aug 3;72(16):6116-26. doi: 10.1021/jo070709p. Epub 2007 Jul 11. [PubMed:17625884 ]
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LOTUS database [Link]

Showing NP-Card for ochromycinone (NP0179726)

MOL for NP0179726 (ochromycinone)

3D MOL for NP0179726 (ochromycinone)

3D SDF for NP0179726 (ochromycinone)

3D-SDF for NP0179726 (ochromycinone)

PDB for NP0179726 (ochromycinone)

3D PDB for NP0179726 (ochromycinone)

SMILES for NP0179726 (ochromycinone)

INCHI for NP0179726 (ochromycinone)

Structure for NP0179726 (ochromycinone)

3D Structure for NP0179726 (ochromycinone)