NP-MRD: Showing NP-Card for Selgin (NP0073960)

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Record Information

Version

2.0

Created at

2022-04-28 19:10:40 UTC

Updated at

2022-04-28 19:10:40 UTC

NP-MRD ID

NP0073960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Selgin

Description

2-(3,4-Dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, also known as tricetin 3'-O-methyl ether or selagin, belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Selgin is found in Artemisia ludoviciana, Chrysanthemum morifolium, Epimedium sagittatum , Oryza sativa , Passiflora palmeri, Poa huecu and Taxus chinensis. Selgin was first documented in 2011 (PMID: 21162116). 2-(3,4-Dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22314384).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.4929    2.2335    1.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333    1.1615    1.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    0.2306    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506    0.2364    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273   -0.7194   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -0.6271   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.5523   -1.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3452   -1.4690   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -2.3053   -1.7838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9236   -0.4240   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3002   -0.2441   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421   -1.0905   -1.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457    0.8406    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    1.7370    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616    2.8046    1.6508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    1.5582    0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1514    0.4854    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410    0.3389    0.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -1.6881   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -1.7555   -0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0401   -2.7704   -1.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0051   -0.7881   -0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3861   -0.8068   -0.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710    1.9599    2.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    3.1021    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198    2.6159    1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045    1.0252    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4811   -2.3659   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1218   -1.8681   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198    0.9708    0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8081    3.6901    1.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    2.2605    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -2.4638   -1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0391   -2.8577   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126   -1.4550   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 22  3  1  0
 18  6  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 19 33  1  0
 21 34  1  0
 23 35  1  0
  7 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1652308171914292D          

 23 25  0  0  0  0            999 V2000
    6.4302   -2.8875    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
    5.0013   -1.2375    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
    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
    6.4302   -0.4125    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
    2.8579    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
    2.8579    0.8250    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
    0.7145   -0.4125    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    0.0000    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
    5.7158   -2.4750    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  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  5  2  0  0  0  0
 14  3  2  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  2  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 11  1  0  0  0  0
 21 16  1  0  0  0  0
 22  1  1  0  0  0  0
 22 14  1  0  0  0  0
 23 12  1  0  0  0  0
 23 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-14-3-7(2-11(20)16(14)21)12-6-10(19)15-9(18)4-8(17)5-13(15)23-12/h2-6,17-18,20-21H,1H3

> <INCHI_KEY>
UGPOBASOHYMNAK-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.734798585421775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.2454525463333335

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.126839391328824

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.576246689996033

> <JCHEM_PKA_STRONGEST_BASIC>
-4.783051821579314

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
81.358

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
selgin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-AUG-19         0                                  
HETATM    1  C   UNK     0      12.003  -5.390   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       9.336  -2.310   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   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  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -0.770   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   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669  -4.620   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
CONECT    1   22                                                            
CONECT    2    7   11                                                       
CONECT    3    7   14                                                       
CONECT    4    8    9                                                       
CONECT    5    8   13                                                       
CONECT    6   10   12                                                       
CONECT    7    2    3   12                                                  
CONECT    8    4    5   17                                                  
CONECT    9    4   15   18                                                  
CONECT   10    6   15   19                                                  
CONECT   11    2   16   20                                                  
CONECT   12    6    7   23                                                  
CONECT   13    5   15   23                                                  
CONECT   14    3   16   22                                                  
CONECT   15    9   10   13                                                  
CONECT   16   11   14   21                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   16                                                            
CONECT   22    1   14                                                       
CONECT   23   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Selagin	ChEBI
Selgin	ChEBI
Tricetin 3'-O-methyl ether	ChEBI
Tricetine 3'-O-methyl ether	ChEBI
Tricetin 3'-methyl ether	Kegg

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

selgin

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H12O7/c1-22-14-3-7(2-11(20)16(14)21)12-6-10(19)15-9(18)4-8(17)5-13(15)23-12/h2-6,17-18,20-21H,1H3

InChI Key

UGPOBASOHYMNAK-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
Artemisia ludoviciana	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Epimedium sagittatum	Plant	KNApSAcK
Oryza sativa	Plant	KNApSAcK
Passiflora palmeri	LOTUS Database	35616633
Poa huecu	LOTUS Database	35616633
Taxus chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Catechol
Methoxybenzene
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:59976 )
tetrahydroxyflavone (CHEBI:59976 )

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	2.73	ALOGPS
logP	2.25	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.36 m³·mol⁻¹	ChemAxon
Polarizability	30.73 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

HMDB0124865

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB083786

KNApSAcK ID

C00034728

Chemspider ID

Not Available

KEGG Compound ID

C19739

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11267045

PDB ID

Not Available

ChEBI ID

59976

Good Scents ID

Not Available

References

General References

Wang Y, Wu Q, Yang XW, Yang X, Wang K: The membrane transport of flavonoids from Crossostephium chinense across the Caco-2 monolayer. Biopharm Drug Dispos. 2011 Jan;32(1):16-24. doi: 10.1002/bdd.735. Epub 2010 Dec 7. [PubMed:21162116 ]
Freire KR, Lins AC, Dorea MC, Santos FA, Camara CA, Silva TM: Palynological origin, phenolic content, and antioxidant properties of honeybee-collected pollen from Bahia, Brazil. Molecules. 2012 Feb 7;17(2):1652-64. doi: 10.3390/molecules17021652. [PubMed:22314384 ]

Showing NP-Card for Selgin (NP0073960)

MOL for NP0073960 (Selgin)

3D MOL for NP0073960 (Selgin)

3D SDF for NP0073960 (Selgin)

3D-SDF for NP0073960 (Selgin)

PDB for NP0073960 (Selgin)

3D PDB for NP0073960 (Selgin)

SMILES for NP0073960 (Selgin)

INCHI for NP0073960 (Selgin)

Structure for NP0073960 (Selgin)

3D Structure for NP0073960 (Selgin)