NP-MRD: Showing NP-Card for 2-hydroxyvertixanthone (NP0143381)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-01 22:07:20 UTC

Updated at

2022-09-01 22:07:21 UTC

NP-MRD ID

NP0143381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxyvertixanthone

Description

2-Hydroxyvertixanthone 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-hydroxyvertixanthone was first documented in 2006 (PMID: 16904330). 2-Hydroxyvertixanthone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.6753   -1.4741   -0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471   -0.4161   -0.0959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -0.6261    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568   -1.8034    0.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    0.5183    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    1.8072   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128    1.8542   -0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3206    2.9660   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    2.8999    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.6689    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    1.6220    0.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.4999    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0021    0.5698    0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -0.6030    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461   -1.7983    0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373   -1.8727    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215   -3.0751    0.6320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464   -0.7008    0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -0.7009    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -1.7602    0.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016    0.4831    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985   -2.4204    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982   -1.5918   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -1.2297    0.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9348    2.6943   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213    3.9415   -0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    3.8355   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357    1.5111    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -0.6386    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -2.7328    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628   -3.4277    0.5781 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 21  2  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 21  5  1  0
 12 18  1  0
 11 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 17 31  1  0
 15 30  1  0
 14 29  1  0
 13 28  1  0
M  END


  Mrv1533004241516062D          

 21 23  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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 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
    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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 10 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0143381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(O)C=CC2=C1C(=O)C1=C(O)C=CC=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c1-20-15(19)12-8(17)5-6-10-13(12)14(18)11-7(16)3-2-4-9(11)21-10/h2-6,16-17H,1H3

> <INCHI_KEY>
RHTSTEXCCXSDAD-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.29829308047387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2,8-dihydroxy-9-oxo-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
3.6559865409999994

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.498636588851243

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.3500005653328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.757169827792054

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
72.8034

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,8-dihydroxy-9-oxoxanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+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  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2390 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

methyl 2,8-dihydroxy-9-oxo-9H-xanthene-1-carboxylate

Traditional Name

methyl 2,8-dihydroxy-9-oxoxanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(O)C=CC2=C1C(=O)C1=C(O)C=CC=C1O2

InChI Identifier

InChI=1S/C15H10O6/c1-20-15(19)12-8(17)5-6-10-13(12)14(18)11-7(16)3-2-4-9(11)21-10/h2-6,16-17H,1H3

InChI Key

RHTSTEXCCXSDAD-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

Not Available

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
Salicylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:68716 )
polyphenol (CHEBI:68716 )
methyl ester (CHEBI:68716 )
xanthones (CHEBI:68716 )

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	2.39	ALOGPS
logP	3.66	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.8 m³·mol⁻¹	ChemAxon
Polarizability	27.3 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

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

Not Available

PDB ID

Not Available

ChEBI ID

68716

Good Scents ID

Not Available

References

General References

Wijeratne EM, Turbyville TJ, Fritz A, Whitesell L, Gunatilaka AA: A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity. Bioorg Med Chem. 2006 Dec 1;14(23):7917-23. doi: 10.1016/j.bmc.2006.07.048. Epub 2006 Aug 10. [PubMed:16904330 ]
LOTUS database [Link]

Showing NP-Card for 2-hydroxyvertixanthone (NP0143381)

MOL for NP0143381 (2-hydroxyvertixanthone)

3D MOL for NP0143381 (2-hydroxyvertixanthone)

3D SDF for NP0143381 (2-hydroxyvertixanthone)

3D-SDF for NP0143381 (2-hydroxyvertixanthone)

PDB for NP0143381 (2-hydroxyvertixanthone)

3D PDB for NP0143381 (2-hydroxyvertixanthone)

SMILES for NP0143381 (2-hydroxyvertixanthone)

INCHI for NP0143381 (2-hydroxyvertixanthone)

Structure for NP0143381 (2-hydroxyvertixanthone)

3D Structure for NP0143381 (2-hydroxyvertixanthone)