NP-MRD: Showing NP-Card for (-)-Muraxanthone (NP0075592)

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Record Information

Version

2.0

Created at

2022-04-28 20:51:08 UTC

Updated at

2022-04-28 20:51:08 UTC

NP-MRD ID

NP0075592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Muraxanthone

Description

Muraxanthone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (-)-Muraxanthone is found in Delairea odorata, Fridericia samydoides and Seneico mikanioides. (-)-Muraxanthone was first documented in 2003 (PMID: 14575443). Based on a literature review very few articles have been published on muraxanthone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222512D          

 39 43  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222512D          

 39 43  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0075592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](OC(=O)C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC3=CC(O)=C(O)C=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O13/c27-8-17-21(33)23(35)25(39-26(36)9-1-3-10(28)4-2-9)24(38-17)18-14(31)7-16-19(22(18)34)20(32)11-5-12(29)13(30)6-15(11)37-16/h1-7,17,21,23-25,27-31,33-35H,8H2/t17-,21-,23+,24+,25-/m1/s1

> <INCHI_KEY>
WVLYNCZFGCFUAG-FUFTYFEXSA-N

> <FORMULA>
C26H22O13

> <MOLECULAR_WEIGHT>
542.449

> <EXACT_MASS>
542.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
52.098199557395645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)oxan-3-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.8297925556666665

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.619067544117975

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.964071608693396

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979193257148019

> <JCHEM_POLAR_SURFACE_AREA>
223.67

> <JCHEM_REFRACTIVITY>
129.6611

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-3-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   33                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10                                                            
CONECT   13    9   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33    8                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36    1                                                       
CONECT   38   36                                                            
CONECT   39   35                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₂O₁₃

Average Mass

542.4490 Da

Monoisotopic Mass

542.10604 Da

IUPAC Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)oxan-3-yl 4-hydroxybenzoate

Traditional Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-3-yl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](OC(=O)C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC3=CC(O)=C(O)C=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C26H22O13/c27-8-17-21(33)23(35)25(39-26(36)9-1-3-10(28)4-2-9)24(38-17)18-14(31)7-16-19(22(18)34)20(32)11-5-12(29)13(30)6-15(11)37-16/h1-7,17,21,23-25,27-31,33-35H,8H2/t17-,21-,23+,24+,25-/m1/s1

InChI Key

WVLYNCZFGCFUAG-FUFTYFEXSA-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
Delairea odorata	LOTUS Database	35616633
Fridericia samydoides	LOTUS Database	35616633
Seneico mikanioides	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Phenolic glycoside
Xanthone
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Glycosyl compound
Chromone
C-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
1,2-diol
Secondary alcohol
Carboxylic acid ester
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Ether
Polyol
Primary alcohol
Alcohol
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	1.66	ALOGPS
logP	1.83	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.66 m³·mol⁻¹	ChemAxon
Polarizability	52.1 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

C00037525

Chemspider ID

23339767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566939

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pauletti PM, Castro-Gamboa I, Siqueira Silva DH, Young MC, Tomazela DM, Eberlin MN, da Silva Bolzani V: New antioxidant C-glucosylxanthones from the stems of Arrabidaea samydoides. J Nat Prod. 2003 Oct;66(10):1384-7. doi: 10.1021/np030100t. [PubMed:14575443 ]

Showing NP-Card for (-)-Muraxanthone (NP0075592)

MOL for NP0075592 ((-)-Muraxanthone)

3D MOL for NP0075592 ((-)-Muraxanthone)

3D SDF for NP0075592 ((-)-Muraxanthone)

3D-SDF for NP0075592 ((-)-Muraxanthone)

PDB for NP0075592 ((-)-Muraxanthone)

3D PDB for NP0075592 ((-)-Muraxanthone)

SMILES for NP0075592 ((-)-Muraxanthone)

INCHI for NP0075592 ((-)-Muraxanthone)

Structure for NP0075592 ((-)-Muraxanthone)

3D Structure for NP0075592 ((-)-Muraxanthone)