NP-MRD: Showing NP-Card for Quercetin 3-sulfate (NP0049884)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:40 UTC

Updated at

2022-03-17 21:19:40 UTC

NP-MRD ID

NP0049884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quercetin 3-sulfate

Description

Quercetin 3-sulfate is found in Ammi visnaga , Flaveria bidentis , Flaveria chloraefolia, Hypericum androsaemum, Oenanthe crocata , Oenothera speciosa and Persicaria hydropiper. Quercetin 3-sulfate was first documented in 1980 (PMID: 7411385).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304202018182D          

 26 28  0  0  0  0            999 V2000
10001.0516 9997.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7659 9998.3974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.1777 9999.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3542 9999.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4782 9997.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7659 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3435 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3435 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6290 9997.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9145 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9145 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6290 9999.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2056 9997.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4911 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4911 9999.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2057 9999.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7794 9999.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2056 9997.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6277 9997.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4804 9999.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0514 9999.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.051410000.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.766010000.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.480410000.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.190510000.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.768010001.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
 13 10  2  0  0  0  0
 11 16  2  0  0  0  0
  9 19  2  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
  1  8  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 20 24  1  0  0  0  0
 22 21  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
  6 20  2  0  0  0  0
 21  6  1  0  0  0  0
  7 21  1  0  0  0  0
M  END


  Mrv1652304202018182D          

 26 28  0  0  0  0            999 V2000
10001.0516 9997.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7659 9998.3974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.1777 9999.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3542 9999.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4782 9997.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7659 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3435 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3435 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6290 9997.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9145 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9145 9999.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6290 9999.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2056 9997.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4911 9998.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4911 9999.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2057 9999.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7794 9999.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2056 9997.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6277 9997.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4804 9999.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0514 9999.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.051410000.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.766010000.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.480410000.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.190510000.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.768010001.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
 13 10  2  0  0  0  0
 11 16  2  0  0  0  0
  9 19  2  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
  1  8  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 20 24  1  0  0  0  0
 22 21  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
  6 20  2  0  0  0  0
 21  6  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049884

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O10S/c16-7-4-10(19)12-11(5-7)24-14(6-1-2-8(17)9(18)3-6)15(13(12)20)25-26(21,22)23/h1-5,16-19H,(H,21,22,23)

> <INCHI_KEY>
DNAYVNOVGHZZLH-UHFFFAOYSA-N

> <FORMULA>
C15H10O10S

> <MOLECULAR_WEIGHT>
382.299

> <EXACT_MASS>
381.99946723

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
33.34786357040208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.680986117666667

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.356070700759556

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.49432336794614

> <JCHEM_PKA_STRONGEST_BASIC>
-5.464930973583517

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
86.854

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quercetin 3-sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0    8668.6308662.905   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0    8669.9638663.675   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0    8670.7328665.006   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8669.1958665.006   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8671.2938662.905   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8669.9638665.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.3088665.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.3088663.679   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.9748662.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.6408663.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6408665.220   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8665.9748665.990   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8663.3178662.909   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9838663.679   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.9838665.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3178665.989   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8660.6558665.990   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8663.3178661.364   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8665.9728661.364   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8671.2978665.990   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.6298665.990   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.6298667.529   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8669.9638668.300   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.2978667.530   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8672.6228668.297   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8669.9678669.834   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6   20   21                                                       
CONECT    7   12    8   21                                                  
CONECT    8    7    9    1                                                  
CONECT    9   19    8   10                                                  
CONECT   10   13    9   11                                                  
CONECT   11   16   12   10                                                  
CONECT   12    7   11                                                       
CONECT   13   10   18   14                                                  
CONECT   14   13   15                                                       
CONECT   15   17   14   16                                                  
CONECT   16   11   15                                                       
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19    9                                                            
CONECT   20   24    6                                                       
CONECT   21   22    6    7                                                  
CONECT   22   21   23                                                       
CONECT   23   26   22   24                                                  
CONECT   24   25   20   23                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-3-(sulfooxy)	ChEBI
Quercetin 3-(hydrogen sulfate)	ChEBI
Quercetin 3-monosulphate	ChEBI
Quercetin 3-O-sulfate	ChEBI
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-3-(sulphooxy)	Generator
Quercetin 3-(hydrogen sulfuric acid)	Generator
Quercetin 3-(hydrogen sulphate)	Generator
Quercetin 3-(hydrogen sulphuric acid)	Generator
Quercetin 3-monosulfate	Generator
Quercetin 3-monosulfuric acid	Generator
Quercetin 3-monosulphuric acid	Generator
Quercetin 3-O-sulfuric acid	Generator
Quercetin 3-O-sulphate	Generator
Quercetin 3-O-sulphuric acid	Generator
Quercetin 3-sulfuric acid	Generator
Quercetin 3-sulphate	Generator
Quercetin 3-sulphuric acid	Generator

Chemical Formula

C₁₅H₁₀O₁₀S

Average Mass

382.2990 Da

Monoisotopic Mass

381.99947 Da

IUPAC Name

[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxidanesulfonic acid

Traditional Name

quercetin 3-sulfate

CAS Registry Number

97736-73-7

SMILES

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

InChI Identifier

InChI=1S/C15H10O10S/c16-7-4-10(19)12-11(5-7)24-14(6-1-2-8(17)9(18)3-6)15(13(12)20)25-26(21,22)23/h1-5,16-19H,(H,21,22,23)

InChI Key

DNAYVNOVGHZZLH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammi visnaga	Plant	KNApSAcK
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Flaveria bidentis	Plant	KNApSAcK
Flaveria chloraefolia	Plant	KNApSAcK
Hypericum androsaemum	LOTUS Database	35616633
Oenanthe crocata	Plant	KNApSAcK
Oenothera speciosa	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-sulfated flavonoids. These are flavonoids that are sulfated at the 3-ring position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Sulfated flavonoids

Direct Parent

3-sulfated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quercetin sulfate (CHEBI:17730 )
tetrahydroxyflavone (CHEBI:17730 )
flavonols (C00616 )
Flavones and Flavonols (C00616 )
Flavones and Flavonols (LMPK12112304 )

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	0.87	ALOGPS
logP	1.68	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.85 m³·mol⁻¹	ChemAxon
Polarizability	33.35 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

FDB021632

KNApSAcK ID

C00004956

Chemspider ID

Not Available

KEGG Compound ID

C00616

BioCyc ID

CPD-1822

BiGG ID

Not Available

Wikipedia Link

Quercetin_3-O-sulfate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17730

Good Scents ID

Not Available

References

General References

Fukuoka M, Yoshihira K, Natori S, Sakamoto K, Iwahara S, Hosaka S, Hirono I: Characterization of mutagenic principles and carcinogenicity of dill weed and seeds. J Pharmacobiodyn. 1980 May;3(5):236-44. doi: 10.1248/bpb1978.3.236. [PubMed:7411385 ]

Showing NP-Card for Quercetin 3-sulfate (NP0049884)

MOL for NP0049884 (Quercetin 3-sulfate)

3D MOL for NP0049884 (Quercetin 3-sulfate)

3D SDF for NP0049884 (Quercetin 3-sulfate)

3D-SDF for NP0049884 (Quercetin 3-sulfate)

PDB for NP0049884 (Quercetin 3-sulfate)

3D PDB for NP0049884 (Quercetin 3-sulfate)

SMILES for NP0049884 (Quercetin 3-sulfate)

INCHI for NP0049884 (Quercetin 3-sulfate)

Structure for NP0049884 (Quercetin 3-sulfate)

3D Structure for NP0049884 (Quercetin 3-sulfate)