NP-MRD: Showing NP-Card for Luteolin 3'-sulfate (NP0052652)

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Record Information

Version

2.0

Created at

2022-04-27 23:37:52 UTC

Updated at

2022-04-27 23:37:52 UTC

NP-MRD ID

NP0052652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolin 3'-sulfate

Description

[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic acid belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Luteolin 3'-sulfate is found in Lachenalia unifolia. [5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1978   -2.6761   -1.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9164   -1.6942   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -1.3696   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -0.2877    0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470    0.1007    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571    1.2030    1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    1.6119    1.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175    0.9047    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9184    1.2898    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232   -0.1907    0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -0.9101   -0.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093   -0.5285   -1.5703 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.9453   -1.5170   -2.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8026   -0.6309   -1.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9192    1.0222   -2.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -0.6003    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489    0.4172    0.5674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    0.1586    0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218    0.9603    0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9454    0.7019    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9659    1.5143    1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613   -0.3785   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646   -1.1766   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -2.2660   -1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301   -0.9182   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1835   -1.9884   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4138    1.7589    1.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    2.4848    2.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0387    2.1169    2.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6470    1.3671   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256   -1.4546   -0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3652    1.8036    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7620    2.3042    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3072   -0.5678   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4779   -2.5647   -1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
  4  5  1  0
  5 16  2  0
 16 10  1  0
 10 11  1  0
 11 12  1  0
 12 15  1  0
 12 13  2  0
 12 14  2  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 19 20  1  0
  6  5  1  0
 18 25  1  0
 21 33  1  0
 22 34  1  0
 24 35  1  0
  3 26  1  0
 19 32  1  0
 16 31  1  0
 15 30  1  0
  9 29  1  0
  7 28  1  0
  6 27  1  0
M  END


  Mrv1652308221912212D          

 25 27  0  0  0  0            999 V2000
    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    0.0000    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
    1.4289    0.0000    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
    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  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
    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
    0.7145   -0.4125    0.0000 O   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
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    0.8250    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
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  2  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 23 12  1  0  0  0  0
 23 14  1  0  0  0  0
 24 13  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  2  0  0  0  0
 25 22  2  0  0  0  0
 25 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(OS(O)(=O)=O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O9S/c16-8-4-10(18)15-11(19)6-12(23-14(15)5-8)7-1-2-9(17)13(3-7)24-25(20,21)22/h1-6,16-18H,(H,20,21,22)

> <INCHI_KEY>
PEQKOWDFKUBMQH-UHFFFAOYSA-N

> <FORMULA>
C15H10O9S

> <MOLECULAR_WEIGHT>
366.3

> <EXACT_MASS>
366.004553076

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
32.99666205157695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
2.5778104656666665

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.577134492291058

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.596594286966094

> <JCHEM_PKA_STRONGEST_BASIC>
-4.848599141082649

> <JCHEM_POLAR_SURFACE_AREA>
150.58999999999997

> <JCHEM_REFRACTIVITY>
84.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin 3'-sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-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  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -0.770   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       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.877   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.797   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0      13.337   1.540   0.000  0.00  0.00           S+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   13                                                       
CONECT    4    8   10                                                       
CONECT    5    8   14                                                       
CONECT    6   11   12                                                       
CONECT    7    1    3   12                                                  
CONECT    8    4    5   16                                                  
CONECT    9    2   13   17                                                  
CONECT   10    4   15   18                                                  
CONECT   11    6   15   19                                                  
CONECT   12    6    7   23                                                  
CONECT   13    3    9   24                                                  
CONECT   14    5   15   23                                                  
CONECT   15   10   11   14                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22   25                                                            
CONECT   23   12   14                                                       
CONECT   24   13   25                                                       
CONECT   25   20   21   22   24                                             
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonate	Generator
[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulphonate	Generator
[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulphonic acid	Generator

Chemical Formula

C₁₅H₁₀O₉S

Average Mass

366.3000 Da

Monoisotopic Mass

366.00455 Da

IUPAC Name

[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic acid

Traditional Name

luteolin 3'-sulfate

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(OS(O)(=O)=O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O9S/c16-8-4-10(18)15-11(19)6-12(23-14(15)5-8)7-1-2-9(17)13(3-7)24-25(20,21)22/h1-6,16-18H,(H,20,21,22)

InChI Key

PEQKOWDFKUBMQH-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, 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
Lachenalia unifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Phenylsulfate
Arylsulfate
Benzopyran
1-benzopyran
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Pyran
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110735 )

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	0.78	ALOGPS
logP	2.58	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.89 m³·mol⁻¹	ChemAxon
Polarizability	33 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

HMDB0133369

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB090415

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

44258151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Luteolin 3'-sulfate (NP0052652)

MOL for NP0052652 (Luteolin 3'-sulfate)

3D MOL for NP0052652 (Luteolin 3'-sulfate)

3D SDF for NP0052652 (Luteolin 3'-sulfate)

3D-SDF for NP0052652 (Luteolin 3'-sulfate)

PDB for NP0052652 (Luteolin 3'-sulfate)

3D PDB for NP0052652 (Luteolin 3'-sulfate)

SMILES for NP0052652 (Luteolin 3'-sulfate)

INCHI for NP0052652 (Luteolin 3'-sulfate)

Structure for NP0052652 (Luteolin 3'-sulfate)

3D Structure for NP0052652 (Luteolin 3'-sulfate)