NP-MRD: Showing NP-Card for 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid (NP0206849)

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Record Information

Version

1.0

Created at

2022-09-05 03:15:00 UTC

Updated at

2022-09-05 03:15:00 UTC

NP-MRD ID

NP0206849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid

Description

6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid is found in Helicteres isora. 6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261505402D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261505402D          

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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  2  0  0  0  0
 35 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(OS(O)(=O)=O)C(OC2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)OC(C1OS(O)(=O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O18S2/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)15(16(13)35-12)36-21-18(39-41(32,33)34)14(26)17(38-40(29,30)31)19(37-21)20(27)28/h1-6,14,17-19,21-23,25-26H,(H,27,28)(H,29,30,31)(H,32,33,34)

> <INCHI_KEY>
QOKHDJUJQRSHRZ-UHFFFAOYSA-N

> <FORMULA>
C21H18O18S2

> <MOLECULAR_WEIGHT>
622.48

> <EXACT_MASS>
621.993456088

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
52.92124240894867

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-3.7251035852471457

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
-2.2155422018850155

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.8535964487202543

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7556813853184083

> <JCHEM_POLAR_SURFACE_AREA>
290.17999999999995

> <JCHEM_REFRACTIVITY>
126.89019999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  S   UNK     0       4.001  -6.930   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0       3.231  -5.596   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.771  -8.264   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   35  S   UNK     0      -2.667  -9.240   0.000  0.00  0.00           S+0
HETATM   36  O   UNK     0      -2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.127  -9.240   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.207  -9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    3   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   11   17                                                  
CONECT   24   21   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
CONECT   31    9   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32    2   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35                                                            
CONECT   39   32   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylate	Generator
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulphooxy)oxane-2-carboxylate	Generator
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulphooxy)oxane-2-carboxylic acid	Generator

Chemical Formula

C₂₁H₁₈O₁₈S₂

Average Mass

622.4800 Da

Monoisotopic Mass

621.99346 Da

IUPAC Name

6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid

Traditional Name

6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(OS(O)(=O)=O)C(OC2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)OC(C1OS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C21H18O18S2/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)15(16(13)35-12)36-21-18(39-41(32,33)34)14(26)17(38-40(29,30)31)19(37-21)20(27)28/h1-6,14,17-19,21-23,25-26H,(H,27,28)(H,29,30,31)(H,32,33,34)

InChI Key

QOKHDJUJQRSHRZ-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
Helicteres isora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
Benzofuran
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
3-furanone
Monosaccharide
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
1,2-diol
Ketone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
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	-0.15	ALOGPS
logP	-3.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	-2.9	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	290.18 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	126.89 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

73981634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid (NP0206849)

MOL for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

3D MOL for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

3D SDF for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

3D-SDF for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

PDB for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

3D PDB for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

SMILES for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

INCHI for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

Structure for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)

3D Structure for NP0206849 (6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid)