NP-MRD: Showing NP-Card for Xanthoquinodin A2 (NP0061523)

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Record Information

Version

2.0

Created at

2022-04-28 06:18:06 UTC

Updated at

2022-04-28 06:18:06 UTC

NP-MRD ID

NP0061523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanthoquinodin A2

Description

Methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]Nonacosa-3,5(14),11,15,19,21(26),22,24,28-nonaene-7-carboxylate 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. Xanthoquinodin A2 is found in Humicola sp. FO-888. Based on a literature review very few articles have been published on methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]Nonacosa-3,5(14),11,15,19,21(26),22,24,28-nonaene-7-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208182D          

 42 48  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282208182D          

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    4.5371   -1.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550    2.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653    2.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602   -0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
  9 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
 10 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 14 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 28 33  1  0  0  0  0
 27 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  2  0  0  0  0
 26 36  1  6  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 21 40  1  0  0  0  0
  8 41  1  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12OC3=CC4=C([C@@H]5C=C[C@@]6(C4)C(=O)C4=CC(C)=CC(O)=C4C(O)=C6C5=O)C(O)=C3C(=O)C1=C(O)CC[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C31H24O11/c1-11-7-14-20(16(33)8-11)26(37)23-24(35)13-5-6-30(23,28(14)39)10-12-9-17-21(25(36)19(12)13)27(38)22-15(32)3-4-18(34)31(22,42-17)29(40)41-2/h5-9,13,18,32-34,36-37H,3-4,10H2,1-2H3/t13-,18-,30-,31+/m0/s1

> <INCHI_KEY>
KIWTVJVARRPBPR-INRCXLCWSA-N

> <FORMULA>
C31H24O11

> <MOLECULAR_WEIGHT>
572.522

> <EXACT_MASS>
572.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.20356201986398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0^{1,19}.0^{3,16}.0^{5,14}.0^{7,12}.0^{21,26}]nonacosa-3(16),4,11,14,19,21,23,25,28-nonaene-7-carboxylate

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.4271309129999996

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.687219525802004

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.119736327438956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.403798926122848

> <JCHEM_POLAR_SURFACE_AREA>
187.88999999999996

> <JCHEM_REFRACTIVITY>
148.71280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0^{1,19}.0^{3,16}.0^{5,14}.0^{7,12}.0^{21,26}]nonacosa-3(16),4,11,14,19,21,23,25,28-nonaene-7-carboxylate

> <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      -3.511   1.248   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.123  -0.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.638  -0.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.542   0.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.930   1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.415   2.329   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.804   3.819   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.298   2.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.884   2.712   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.301   1.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.007   0.112   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.333  -1.393   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.828   0.300   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.207   1.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.477   2.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.521   4.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.837   4.112   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.070   5.447   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.709   3.045   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.683   1.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.925   3.292   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.103   2.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.833   0.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.384   0.260   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.010  -0.208   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.459   0.315   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.729   1.831   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.177   2.355   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.355   1.363   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.084  -0.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.636  -0.677   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.366  -2.193   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.448   3.871   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.551   2.824   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.822   4.340   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.188  -1.201   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.558  -2.696   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.740  -1.724   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.469  -3.241   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.196   4.808   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.122   4.405   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.219  -1.324   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   42                                                  
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   41                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   13   20                                             
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16    9   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   10                                                       
CONECT   21   15   22   40                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   14                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27   31   36                                             
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34   27   22   35                                                  
CONECT   35   34                                                            
CONECT   36   26   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   21                                                            
CONECT   41    8                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0,.0,.0,.0,.0,]nonacosa-3,5(14),11,15,19,21(26),22,24,28-nonaene-7-carboxylic acid	Generator

Chemical Formula

C₃₁H₂₄O₁₁

Average Mass

572.5220 Da

Monoisotopic Mass

572.13186 Da

IUPAC Name

methyl (1R,7S,8S,17S)-8,11,15,20,22-pentahydroxy-24-methyl-13,18,27-trioxo-6-oxaheptacyclo[15.10.2.0^{1,19}.0^{3,16}.0^{5,14}.0^{7,12}.0^{21,26}]nonacosa-3(16),4,11,14,19,21,23,25,28-nonaene-7-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12OC3=CC4=C([C@@H]5C=C[C@@]6(C4)C(=O)C4=CC(C)=CC(O)=C4C(O)=C6C5=O)C(O)=C3C(=O)C1=C(O)CC[C@@H]2O

InChI Identifier

InChI=1S/C31H24O11/c1-11-7-14-20(16(33)8-11)26(37)23-24(35)13-5-6-30(23,28(14)39)10-12-9-17-21(25(36)19(12)13)27(38)22-15(32)3-4-18(34)31(22,42-17)29(40)41-2/h5-9,13,18,32-34,36-37H,3-4,10H2,1-2H3/t13-,18-,30-,31+/m0/s1

InChI Key

KIWTVJVARRPBPR-INRCXLCWSA-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
Humicola sp. FO-888	-	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

Xanthone
Chromone
1-naphthol
Naphthalene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Cyclohexenone
Phenol
Hydroxy acid
Benzenoid
Vinylogous acid
Methyl ester
Ketone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Enol
Carboxylic acid derivative
Polyol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
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	1.73	ALOGPS
logP	2.43	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.12	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	187.89 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	148.71 m³·mol⁻¹	ChemAxon
Polarizability	57.2 Å³	ChemAxon
Number of Rings	7	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

10291186

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Xanthoquinodin A2 (NP0061523)

MOL for NP0061523 (Xanthoquinodin A2)

3D MOL for NP0061523 (Xanthoquinodin A2)

3D SDF for NP0061523 (Xanthoquinodin A2)

3D-SDF for NP0061523 (Xanthoquinodin A2)

PDB for NP0061523 (Xanthoquinodin A2)

3D PDB for NP0061523 (Xanthoquinodin A2)

SMILES for NP0061523 (Xanthoquinodin A2)

INCHI for NP0061523 (Xanthoquinodin A2)

Structure for NP0061523 (Xanthoquinodin A2)

3D Structure for NP0061523 (Xanthoquinodin A2)