NP-MRD: Showing NP-Card for 7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone (NP0296477)

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Record Information

Version

2.0

Created at

2022-09-10 06:04:33 UTC

Updated at

2022-09-10 06:04:33 UTC

NP-MRD ID

NP0296477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone

Description

7A,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7,7a,8,10,13,15,15a-octahydro-1H-2-oxahexaphene-1,8,10,13,15-pentone 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. 7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone is found in Streptomyces albidoflavus. 7A,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7,7a,8,10,13,15,15a-octahydro-1H-2-oxahexaphene-1,8,10,13,15-pentone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151516392D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004151516392D          

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M  END
> <DATABASE_ID>
NP0296477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C3=C(C(O)=C2C1=O)C(=O)C1(O)C2=C(O)C4=C(C=C(C)OC4=O)C=C2CCC1(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H18O12/c1-8-5-10-6-9-3-4-26(36)23(33)16-17(24(34)27(26,37)18(9)22(32)13(10)25(35)39-8)21(31)15-14(20(16)30)11(28)7-12(38-2)19(15)29/h5-7,30-32,36-37H,3-4H2,1-2H3

> <INCHI_KEY>
ODZAAMMLLKLWSB-UHFFFAOYSA-N

> <FORMULA>
C27H18O12

> <MOLECULAR_WEIGHT>
534.429

> <EXACT_MASS>
534.07982602

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
49.984622247678274

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7,7a,8,10,13,15,15a-octahydro-1H-2-oxahexaphene-1,8,10,13,15-pentone

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.804041647666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.824683168800712

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.155072903203111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.639522841408449

> <JCHEM_POLAR_SURFACE_AREA>
204.95999999999995

> <JCHEM_REFRACTIVITY>
134.27579999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.637  -6.146   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.167  -6.323   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.085  -5.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.473  -3.673   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.391  -2.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.779  -1.024   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.921  -2.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.839  -1.377   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.227   0.036   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.369  -1.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.287  -0.317   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.675   1.096   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.816  -0.494   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.205   0.920   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      18.734   0.743   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.264   0.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.876  -0.847   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.406  -1.024   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.018  -2.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.548  -2.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.160  -4.027   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.690  -4.203   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      24.242  -5.263   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.712  -5.087   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.794  -6.323   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.100  -3.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.570  -3.497   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      19.652  -4.733   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.958  -2.083   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.428  -1.907   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      19.040  -3.320   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.511  -3.143   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.122  -4.557   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.981  -2.967   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.063  -4.203   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      15.675  -5.617   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.533  -4.027   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.615  -5.263   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.227  -6.676   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   30                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   17   30                                                  
CONECT   30   29   13   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   10   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    7   38                                                  
CONECT   38   37    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₁₈O₁₂

Average Mass

534.4290 Da

Monoisotopic Mass

534.07983 Da

IUPAC Name

7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7,7a,8,10,13,15,15a-octahydro-1H-2-oxahexaphene-1,8,10,13,15-pentone

Traditional Name

7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C3=C(C(O)=C2C1=O)C(=O)C1(O)C2=C(O)C4=C(C=C(C)OC4=O)C=C2CCC1(O)C3=O

InChI Identifier

InChI=1S/C27H18O12/c1-8-5-10-6-9-3-4-26(36)23(33)16-17(24(34)27(26,37)18(9)22(32)13(10)25(35)39-8)21(31)15-14(20(16)30)11(28)7-12(38-2)19(15)29/h5-7,30-32,36-37H,3-4H2,1-2H3

InChI Key

ODZAAMMLLKLWSB-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 albidoflavus	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
9,10-anthraquinone
1,4-anthraquinone
Naphthopyranone
Phenanthrene
Naphthopyran
Isocoumarin
Benzopyran
2-benzopyran
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Lactone
Ketone
1,2-diol
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	3.19	ALOGPS
logP	3.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	204.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.28 m³·mol⁻¹	ChemAxon
Polarizability	49.98 Å³	ChemAxon
Number of Rings	6	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

85148896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone (NP0296477)

MOL for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

3D MOL for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

3D SDF for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

3D-SDF for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

PDB for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

3D PDB for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

SMILES for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

INCHI for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

Structure for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)

3D Structure for NP0296477 (7a,9,14,15a,16-pentahydroxy-12-methoxy-3-methyl-6,7-dihydro-2-oxahexaphene-1,8,10,13,15-pentone)