NP-MRD: Showing NP-Card for {5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid (NP0269959)

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Record Information

Version

2.0

Created at

2022-09-08 15:35:56 UTC

Updated at

2022-09-08 15:35:57 UTC

NP-MRD ID

NP0269959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid

Description

NSC646851 belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. NSC646851 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.4701   -0.4026   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147    0.1672    0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446   -0.0082    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964    0.6079    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126    0.4808    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768    1.1051    1.9558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991    2.6876    1.7570 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.7006    2.8525    2.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069    3.7024    2.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9235    3.0055    0.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -0.2939    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107   -0.9276   -0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.7730   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244   -1.7107   -1.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6703   -1.8709   -1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -2.6443   -2.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.2444   -1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -1.3795   -1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4247   -2.0715   -2.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506   -0.7215   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523    0.0418    0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9414    0.7146    1.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    0.1449    0.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -0.4532   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3374    0.3153   -0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8408   -1.3949   -0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1263   -0.5404   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6782    1.2135    1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    3.9768    0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232   -1.2748   -1.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425   -2.2054   -2.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287   -2.9185   -3.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -0.8485   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866    0.7190    2.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653    1.7591    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9104    0.1898    1.8881 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 10  1  0
  7  8  2  0
  7  9  2  0
  5 11  2  0
 11 12  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 24  2  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  2  0
 20 18  1  0
 18 19  2  0
 12 13  2  0
 13  3  1  0
 24 11  1  0
 18 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 14 31  1  0
 16 32  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
 20 33  1  0
 13 30  1  0
M  END


  Mrv1533004231522492D          

 24 26  0  0  0  0            999 V2000
   -1.3480   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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  2  0  0  0  0
 16 18  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 14 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OS(O)(=O)=O)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O8S/c1-7-3-10(16)14-11(17)5-8-4-9(21-2)6-12(23-24(18,19)20)13(8)15(14)22-7/h3-6,17H,1-2H3,(H,18,19,20)

> <INCHI_KEY>
VNCBXISCBOHKSC-UHFFFAOYSA-N

> <FORMULA>
C15H12O8S

> <MOLECULAR_WEIGHT>
352.31

> <EXACT_MASS>
352.02528852

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.53481282523263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-hydroxy-8-methoxy-2-methyl-4-oxo-4H-benzo[h]chromen-10-yl}oxidanesulfonic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
2.2709147706666664

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.195013786790381

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.1715607635364433

> <JCHEM_PKA_STRONGEST_BASIC>
-4.730800689637732

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
83.97420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.746  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874  -1.183   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0       2.104   0.151   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       1.334   1.485   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.437   0.921   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.770  -0.619   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -2.516   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.184  -7.851   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494  -1.183   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    5   12   22                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
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   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22    3                                                       
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₈S

Average Mass

352.3100 Da

Monoisotopic Mass

352.02529 Da

IUPAC Name

{5-hydroxy-8-methoxy-2-methyl-4-oxo-4H-benzo[h]chromen-10-yl}oxidanesulfonic acid

Traditional Name

{5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(OS(O)(=O)=O)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1

InChI Identifier

InChI=1S/C15H12O8S/c1-7-3-10(16)14-11(17)5-8-4-9(21-2)6-12(23-24(18,19)20)13(8)15(14)22-7/h3-6,17H,1-2H3,(H,18,19,20)

InChI Key

VNCBXISCBOHKSC-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 naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Chromone
2-naphthol
Arylsulfate
Benzopyran
Naphthalene
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Sulfuric acid ester
Pyran
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Vinylogous acid
Heteroaromatic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	0.41	ALOGPS
logP	2.27	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.97 m³·mol⁻¹	ChemAxon
Polarizability	32.53 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

5465366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid (NP0269959)

MOL for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

3D MOL for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

3D SDF for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

3D-SDF for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

PDB for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

3D PDB for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

SMILES for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

INCHI for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

Structure for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)

3D Structure for NP0269959 ({5-hydroxy-8-methoxy-2-methyl-4-oxobenzo[h]chromen-10-yl}oxidanesulfonic acid)