NP-MRD: Showing NP-Card for Onysilin (NP0138747)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-06-29 18:34:20 UTC

Updated at

2022-06-29 18:34:20 UTC

NP-MRD ID

NP0138747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Onysilin

Description

Onysilin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Onysilin is found in Miliusa balansae and Onychium siliculosum. It was first documented in 2010 (PMID: 20465823). Based on a literature review a small amount of articles have been published on Onysilin (PMID: 32433929) (PMID: 25442273) (PMID: 35807266).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9168    1.9665   -1.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0889    1.2008   -0.5871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9494    0.6206   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972    0.7833   -0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5634    0.2156   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683   -0.5422    1.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -0.7259    1.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363   -1.4648    2.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0340   -0.1398    1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2935   -0.3176    1.7098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1253   -1.4159    1.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581   -1.1237    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929   -2.1617    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -0.5440    1.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8788    0.4523    0.2728 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0814    0.3445   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    1.2235   -0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914    1.2053   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4011    0.2448   -2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786   -0.6402   -2.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2189   -0.6059   -1.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    0.3515   -0.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7064    1.3385   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988    2.4934   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472    2.7589   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.3735   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -1.9543    3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758   -2.3668    1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9875   -1.4130    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778   -1.3350    0.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471   -1.3268    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.0498    2.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437    1.4657    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    1.9846    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1024    1.9195   -0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3287    0.2417   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941   -1.3748   -3.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3934   -1.2832   -1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  1  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 22  1  0
 22  5  1  0
  5  4  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  4  3  1  0
 21 16  1  0
  5  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  8 27  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  1
  4 26  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END


  Mrv1652306292220342D          

 22 24  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  5 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-20-14-9-13-15(16(19)17(14)21-2)11(18)8-12(22-13)10-6-4-3-5-7-10/h3-7,9,12,19H,8H2,1-2H3/t12-/m0/s1

> <INCHI_KEY>
FAUVORGACLCWKX-LBPRGKRZSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.31

> <EXACT_MASS>
300.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.38869440899351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-hydroxy-6,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.126896162333333

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.781466280198028

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.258995583362983

> <JCHEM_PKA_STRONGEST_BASIC>
-4.255247024399211

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.25440000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-6,7-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   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  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    3                                                       
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    5                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3100 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

73695-94-0

SMILES

COC1=C(OC)C(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H16O5/c1-20-14-9-13-15(16(19)17(14)21-2)11(18)8-12(22-13)10-6-4-3-5-7-10/h3-7,9,12,19H,8H2,1-2H3/t12-/m0/s1

InChI Key

FAUVORGACLCWKX-LBPRGKRZSA-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
Miliusa balansae	LOTUS Database	35616633
Onychium siliculosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008149

Chemspider ID

21186413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12041831

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vasas A, Lajter I, Kusz N, Forgo P, Jakab G, Fazakas C, Wilhelm I, Krizbai IA, Hohmann J: Flavonoid, stilbene and diarylheptanoid constituents of Persicaria maculosa Gray and cytotoxic activity of the isolated compounds. Fitoterapia. 2020 Sep;145:104610. doi: 10.1016/j.fitote.2020.104610. Epub 2020 May 17. [PubMed:32433929 ]
Kuete V, Nkuete AH, Mbaveng AT, Wiench B, Wabo HK, Tane P, Efferth T: Cytotoxicity and modes of action of 4'-hydroxy-2',6'-dimethoxychalcone and other flavonoids toward drug-sensitive and multidrug-resistant cancer cell lines. Phytomedicine. 2014 Oct 15;21(12):1651-7. doi: 10.1016/j.phymed.2014.08.001. Epub 2014 Sep 15. [PubMed:25442273 ]
Do LTM, Sichaem J: New Flavonoid Derivatives from Melodorum fruticosum and Their alpha-Glucosidase Inhibitory and Cytotoxic Activities. Molecules. 2022 Jun 22;27(13):4023. doi: 10.3390/molecules27134023. [PubMed:35807266 ]
Chao WW, Lin BF: Isolation and identification of bioactive compounds in Andrographis paniculata (Chuanxinlian). Chin Med. 2010 May 13;5:17. doi: 10.1186/1749-8546-5-17. [PubMed:20465823 ]

Showing NP-Card for Onysilin (NP0138747)

MOL for NP0138747 (Onysilin)

3D MOL for NP0138747 (Onysilin)

3D SDF for NP0138747 (Onysilin)

3D-SDF for NP0138747 (Onysilin)

PDB for NP0138747 (Onysilin)

3D PDB for NP0138747 (Onysilin)

SMILES for NP0138747 (Onysilin)

INCHI for NP0138747 (Onysilin)

Structure for NP0138747 (Onysilin)

3D Structure for NP0138747 (Onysilin)