NP-MRD: Showing NP-Card for 2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid (NP0145081)

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Record Information

Version

2.0

Created at

2022-09-02 00:12:23 UTC

Updated at

2022-09-02 00:12:23 UTC

NP-MRD ID

NP0145081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid

Description

Penixanacid A 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. 2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid is found in Penicillium chrysogenum. 2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid was first documented in 2015 (PMID: 25611519). Based on a literature review very few articles have been published on Penixanacid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    6.3341    0.7001    0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    0.0719    0.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.7973    0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106    2.0089    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    0.1085    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649   -1.2807   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882   -1.9794   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -1.3264   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265   -1.9882   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157   -3.2295   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.2576   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339   -1.8889   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178   -1.1844   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8400   -1.8515   -0.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5311    0.1635    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3205    0.8075    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2972    2.2408    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4006    2.8560    0.3913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    2.9050    0.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265    0.1065    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    0.6962    0.1771 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1749    0.0278    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    0.7413    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066    2.0853    0.4120 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8173    0.5138    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292    1.7667    0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0157    0.2019   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -1.7876   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -3.0542   -0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935   -2.9588   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3417   -2.2277    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4685    0.7168    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8216    3.6882   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    2.8107    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  5  1  0
 22  8  1  0
 20 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 19 33  1  0
 24 34  1  0
M  END


  Mrv1652309022202122D          

 24 26  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C2C(=O)C3=CC(O)=CC(C(O)=O)=C3OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O8/c1-23-16(22)8-3-2-7-11(18)9-4-6(17)5-10(15(20)21)13(9)24-14(7)12(8)19/h2-5,17,19H,1H3,(H,20,21)

> <INCHI_KEY>
PTYYVBPXCVLOAP-UHFFFAOYSA-N

> <FORMULA>
C16H10O8

> <MOLECULAR_WEIGHT>
330.248

> <EXACT_MASS>
330.037567282

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
31.061253198793565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-6-(methoxycarbonyl)-9-oxo-9H-xanthene-4-carboxylic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.6635694489999997

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.197633831593402

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1680088210705204

> <JCHEM_PKA_STRONGEST_BASIC>
-3.832248397974649

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
80.0596

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23                                                  
CONECT   23   22    5   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₈

Average Mass

330.2480 Da

Monoisotopic Mass

330.03757 Da

IUPAC Name

2,5-dihydroxy-6-(methoxycarbonyl)-9-oxo-9H-xanthene-4-carboxylic acid

Traditional Name

2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C2C(=O)C3=CC(O)=CC(C(O)=O)=C3OC2=C1O

InChI Identifier

InChI=1S/C16H10O8/c1-23-16(22)8-3-2-7-11(18)9-4-6(17)5-10(15(20)21)13(9)24-14(7)12(8)19/h2-5,17,19H,1H3,(H,20,21)

InChI Key

PTYYVBPXCVLOAP-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
Penicillium chrysogenum	LOTUS Database	35616633

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
Hydroxybenzoic acid
Salicylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Dicarboxylic acid or derivatives
Pyran
Benzenoid
Heteroaromatic compound
Methyl ester
Vinylogous acid
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	2.11	ALOGPS
logP	2.66	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.06 m³·mol⁻¹	ChemAxon
Polarizability	31.06 Å³	ChemAxon
Number of Rings	3	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

35516681

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118735496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guo W, Li D, Peng J, Zhu T, Gu Q, Li D: Penicitols A-C and penixanacid A from the mangrove-derived Penicillium chrysogenum HDN11-24. J Nat Prod. 2015 Feb 27;78(2):306-10. doi: 10.1021/np500586r. Epub 2015 Jan 22. [PubMed:25611519 ]
LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid (NP0145081)

MOL for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

3D MOL for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

3D SDF for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

3D-SDF for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

PDB for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

3D PDB for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

SMILES for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

INCHI for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

Structure for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)

3D Structure for NP0145081 (2,5-dihydroxy-6-(methoxycarbonyl)-9-oxoxanthene-4-carboxylic acid)