NP-MRD: Showing NP-Card for Sulfuretin (NP0137349)

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Record Information

Version

2.0

Created at

2022-05-30 16:49:44 UTC

Updated at

2022-05-30 16:49:44 UTC

NP-MRD ID

NP0137349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sulfuretin

Description

2-[(3,4-Dihydroxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Thus, 2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one is considered to be a flavonoid lipid molecule. Sulfuretin is found in Albizia julibrissin, Astragalus microcephalus, Bahiopsis laciniata, Bidens aurea, Bidens pilosa, Bidens tripartita, Carex appressa, Cotinus coggygria, Dalbergia odorifera, Dipteryx lacunifera, Dipteryx odorata, Lasthenia californica, Passiflora sexflora, Sophora alopecuroides, Toxicodendron vernicifluum and Viguiera dentata. 2-[(3,4-Dihydroxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    0.2862    1.4387    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    0.4256    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001   -0.8001   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -1.1365   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282   -0.3590   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851    0.9280   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    1.6358   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4140    1.0279    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5894    1.7028    0.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2669   -0.2449    0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3406   -0.8366    1.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006   -0.9452    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5349   -1.5893   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   -0.9179   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959   -1.3085   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0256   -0.4950    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3480   -0.8989    0.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992    0.7285    0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    1.1140    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3447    0.3100    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -2.1413   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783    1.3885   -1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4709    2.6498   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8060    2.6298   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2848   -1.7738    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9836   -1.9664    0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3041   -2.2704   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6111   -1.8022   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4384    1.4243    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990    2.0822    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 20  2  0
 20 19  1  0
 19 18  2  0
 20  2  1  0
  2  1  2  0
  2  3  1  0
  3 13  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 18 16  1  0
  6  5  1  0
 13 14  1  0
 17 28  1  0
 15 27  1  0
 19 30  1  0
 18 29  1  0
  4 21  1  0
 12 26  1  0
 11 25  1  0
  9 24  1  0
  7 23  1  0
  6 22  1  0
M  END


  Mrv1652308231918222D          

 20 22  0  0  0  0            999 V2000
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  6  8  1  4  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 15 10  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  1  0  0  0  0
 19 15  2  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C(=O)C(O2)=CC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-2-3-10-13(7-9)20-14(15(10)19)6-8-1-4-11(17)12(18)5-8/h1-7,16-18H

> <INCHI_KEY>
RGNXWPVNPFAADO-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.052533787850543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.2915783513333334

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.857200643283127

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.624426562901219

> <JCHEM_PKA_STRONGEST_BASIC>
-5.464336592176825

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
72.989

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfuretin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.203  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.877  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.433  -3.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.107  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.203  -4.565   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.877  -4.565   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    4    8                                                       
CONECT    2    3    9                                                       
CONECT    3    2   10                                                       
CONECT    4    1   11                                                       
CONECT    5    8   12                                                       
CONECT    6    8   14                                                       
CONECT    7    9   13                                                       
CONECT    8    1    5    6                                                  
CONECT    9    2    7   16                                                  
CONECT   10    3   13   15                                                  
CONECT   11    4   12   17                                                  
CONECT   12    5   11   18                                                  
CONECT   13    7   10   20                                                  
CONECT   14    6   15   20                                                  
CONECT   15   10   14   19                                                  
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

sulfuretin

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1)C(=O)C(O2)=CC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O5/c16-9-2-3-10-13(7-9)20-14(15(10)19)6-8-1-4-11(17)12(18)5-8/h1-7,16-18H

InChI Key

RGNXWPVNPFAADO-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
Albizia julibrissin	LOTUS Database	35616633
Astragalus microcephalus	LOTUS Database	35616633
Bahiopsis laciniata	LOTUS Database	35616633
Bidens ferulifolia	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Bidens tripartita	LOTUS Database	35616633
Carex appressa	LOTUS Database	35616633
Cotinus coggygria	LOTUS Database	35616633
Dalbergia odorifera	LOTUS Database	35616633
Dipteryx lacunifera	LOTUS Database	35616633
Dipteryx odorata	LOTUS Database	35616633
Lasthenia californica	LOTUS Database	35616633
Passiflora sexflora	LOTUS Database	35616633
Sophora alopecuroides	LOTUS Database	35616633
Toxicodendron vernicifluum	LOTUS Database	35616633
Viguiera dentata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzofuran
Coumaran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130008 )
an aurone (CPD-7389 )

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	3.09	ALOGPS
logP	2.29	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.62	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.99 m³·mol⁻¹	ChemAxon
Polarizability	27.05 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

HMDB0137516

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB092991

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

67111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sulfuretin (NP0137349)

MOL for NP0137349 (Sulfuretin)

3D MOL for NP0137349 (Sulfuretin)

3D SDF for NP0137349 (Sulfuretin)

3D-SDF for NP0137349 (Sulfuretin)

PDB for NP0137349 (Sulfuretin)

3D PDB for NP0137349 (Sulfuretin)

SMILES for NP0137349 (Sulfuretin)

INCHI for NP0137349 (Sulfuretin)

Structure for NP0137349 (Sulfuretin)

3D Structure for NP0137349 (Sulfuretin)