NP-MRD: Showing NP-Card for Xanthomegnin (NP0082469)

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Record Information

Version

2.0

Created at

2022-04-29 03:31:07 UTC

Updated at

2022-04-29 03:31:07 UTC

NP-MRD ID

NP0082469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanthomegnin

Description

Xanthomegnine belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Xanthomegnin is found in Nannizzia cajetani, Aspergillus melleus, Aspergillus sulphureus, Microsporium cookei, Penicillium viridicatum, Trichophyton megnini, Trichophyton rubrum and Trichophyton violaceum. Based on a literature review very few articles have been published on Xanthomegnine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292205312D          

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  5 11  1  0  0  0  0
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 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
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  1  0  0  0
 19 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
  1 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  2  0  0  0  0
 37 41  1  1  0  0  0
 32 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(=O)C2=C(C=C3C[C@@H](C)OC(=O)C3=C2O)C1=O)C1=C(OC)C(=O)C2=C(C(O)=C3C(=O)O[C@H](C)CC3=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O12/c1-9-5-11-7-13-17(23(33)15(11)29(37)41-9)25(35)19(27(39-3)21(13)31)20-26(36)18-14(22(32)28(20)40-4)8-12-6-10(2)42-30(38)16(12)24(18)34/h7-10,33-34H,5-6H2,1-4H3/t9-,10-/m1/s1

> <INCHI_KEY>
WICHONPZVIYWIJ-NXEZZACHSA-N

> <FORMULA>
C30H22O12

> <MOLECULAR_WEIGHT>
574.494

> <EXACT_MASS>
574.111126148

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
57.15700810050933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-10-hydroxy-8-[(3R)-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-8-yl]-7-methoxy-3-methyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-1,6,9-trione

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
4.1279634099999996

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.280894253859358

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.678805377557839

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393697185580163

> <JCHEM_POLAR_SURFACE_AREA>
179.79999999999998

> <JCHEM_REFRACTIVITY>
146.9828

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-10-hydroxy-8-[(3R)-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl]-7-methoxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -7.700   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  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2    7   35                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9                                                            
CONECT   11    5   12   17                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   29                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   15                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   24                                                            
CONECT   29   19                                                            
CONECT   30   12   31                                                       
CONECT   31   30                                                            
CONECT   32    2   33   42                                                  
CONECT   33   32   34   39                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34    1                                                       
CONECT   36   34   37                                                       
CONECT   37   36   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   33   40                                                  
CONECT   40   39                                                            
CONECT   41   37                                                            
CONECT   42   32                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
Xanthomegnin	MeSH
3,3'-Bis(2-methoxy-5-hydroxy-7-(2-hydroxypropyl)-8- carboxyl-1,4-naphthoquinone lactone)	MeSH

Chemical Formula

C₃₀H₂₂O₁₂

Average Mass

574.4940 Da

Monoisotopic Mass

574.11113 Da

IUPAC Name

(3R)-10-hydroxy-8-[(3R)-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-8-yl]-7-methoxy-3-methyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-1,6,9-trione

Traditional Name

(3R)-10-hydroxy-8-[(3R)-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl]-7-methoxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,9-trione

CAS Registry Number

Not Available

SMILES

COC1=C(C(=O)C2=C(C=C3C[C@@H](C)OC(=O)C3=C2O)C1=O)C1=C(OC)C(=O)C2=C(C(O)=C3C(=O)O[C@H](C)CC3=C2)C1=O

InChI Identifier

InChI=1S/C30H22O12/c1-9-5-11-7-13-17(23(33)15(11)29(37)41-9)25(35)19(27(39-3)21(13)31)20-26(36)18-14(22(32)28(20)40-4)8-12-6-10(2)42-30(38)16(12)24(18)34/h7-10,33-34H,5-6H2,1-4H3/t9-,10-/m1/s1

InChI Key

WICHONPZVIYWIJ-NXEZZACHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arthroderma cajetani	-	KNApSAcK
Aspergillus melleus	Fungi	KNApSAcK
Aspergillus sulphureus	Fungi	KNApSAcK
Microsporium cookei	-	KNApSAcK
Penicillium viridicatum	Fungi	KNApSAcK
Trichophyton megnini	Fungi	KNApSAcK
Trichophyton rubrum	Fungi	KNApSAcK
Trichophyton violaceum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Vinylogous ester
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	3.24	ALOGPS
logP	4.13	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	179.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.98 m³·mol⁻¹	ChemAxon
Polarizability	57.16 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

2297394

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3032411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Xanthomegnin (NP0082469)

MOL for NP0082469 (Xanthomegnin)

3D MOL for NP0082469 (Xanthomegnin)

3D SDF for NP0082469 (Xanthomegnin)

3D-SDF for NP0082469 (Xanthomegnin)

PDB for NP0082469 (Xanthomegnin)

3D PDB for NP0082469 (Xanthomegnin)

SMILES for NP0082469 (Xanthomegnin)

INCHI for NP0082469 (Xanthomegnin)

Structure for NP0082469 (Xanthomegnin)

3D Structure for NP0082469 (Xanthomegnin)