NP-MRD: Showing NP-Card for 5,7,4'-Trihydroxyflavanone 7-sulfate (NP0060405)

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Record Information

Version

2.0

Created at

2022-04-28 05:28:07 UTC

Updated at

2022-04-28 05:28:07 UTC

NP-MRD ID

NP0060405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trihydroxyflavanone 7-sulfate

Description

Naringenin 7-sulfate belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. 5,7,4'-Trihydroxyflavanone 7-sulfate is found in Cunninghamella elegans. Naringenin 7-sulfate 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
    0.3477   -3.3415   -1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2214   -2.2739   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -1.9049   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149   -0.4819   -0.4675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5798    0.0650    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374    1.4167   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0134    1.9744    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9693    1.1331    0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1552    1.6883    1.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527   -0.2058    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5473   -0.7512    0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    0.2943    0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470   -0.0029   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112    0.9745   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2855    0.6375   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969    1.6194   -0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759    1.7508    0.7901 S   0  0  2  0  0  6  0  0  0  0  0  0
    5.3909    3.1897    1.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5362    1.1003    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    1.0004    2.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -0.6240   -1.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -1.6015   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630   -2.8316   -1.6156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -1.3080   -0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273   -2.0529    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -2.6162   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757   -0.4526   -1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901    2.0809   -0.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142    3.0471    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3325    2.6696    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4774   -0.8892    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -1.8204    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    1.9738    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616    1.0157    2.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6038   -0.8487   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4444   -3.6243   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 15  2  0
 15 16  1  0
 17 16  1  6
 17 20  1  0
 17 18  2  0
 17 19  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 12  4  1  0
 11  5  1  0
 13 24  1  0
  4 27  1  6
  3 25  1  0
  3 26  1  0
 23 36  1  0
 21 35  1  0
 20 34  1  0
 14 33  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
M  END


  Mrv1652310111918152D          

 25 27  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  1  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  2  0  0  0  0
 24 21  2  0  0  0  0
 24 23  1  0  0  0  0
 13 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0060405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-6,13,16-17H,7H2,(H,19,20,21)/t13-/m0/s1

> <INCHI_KEY>
LCXKYLMSILXZFG-ZDUSSCGKSA-N

> <FORMULA>
C15H12O8S

> <MOLECULAR_WEIGHT>
352.31

> <EXACT_MASS>
352.02528852

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.65064665825194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
2.3597947039999996

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.197726676092547

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.414352328225105

> <JCHEM_PKA_STRONGEST_BASIC>
-4.955325823130645

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
81.2816

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   25  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   23                                                  
CONECT   11    5   15   17                                                  
CONECT   12    7   15   18                                                  
CONECT   13    7    8   22   25                                             
CONECT   14    6   15   22                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   13   14                                                       
CONECT   23   10   24                                                       
CONECT   24   19   20   21   23                                             
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Naringenin 7-sulfuric acid	Generator
Naringenin 7-sulphate	Generator
Naringenin 7-sulphuric acid	Generator

Chemical Formula

C₁₅H₁₂O₈S

Average Mass

352.3100 Da

Monoisotopic Mass

352.02529 Da

IUPAC Name

[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxidanesulfonic acid

Traditional Name

[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-6,13,16-17H,7H2,(H,19,20,21)/t13-/m0/s1

InChI Key

LCXKYLMSILXZFG-ZDUSSCGKSA-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
Cunninghamella elegans	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Arylsulfate
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Vinylogous acid
Organic sulfuric acid or derivatives
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	0.42	ALOGPS
logP	2.36	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.28 m³·mol⁻¹	ChemAxon
Polarizability	32.65 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

HMDB0240547

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093742

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

101019951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,4'-Trihydroxyflavanone 7-sulfate (NP0060405)

MOL for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

3D MOL for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

3D SDF for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

3D-SDF for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

PDB for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

3D PDB for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

SMILES for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

INCHI for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

Structure for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)

3D Structure for NP0060405 (5,7,4'-Trihydroxyflavanone 7-sulfate)