NP-MRD: Showing NP-Card for Lanceolatin A(flavonoid) (NP0052401)

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Record Information

Version

2.0

Created at

2022-04-27 23:27:42 UTC

Updated at

2022-04-27 23:27:42 UTC

NP-MRD ID

NP0052401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lanceolatin A(flavonoid)

Description

Lanceolatin a 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. Thus, lanceolatin a is considered to be a flavonoid. Lanceolatin A(flavonoid) is found in Tephrosia apollinea , Tephrosia lanceolata and Tephrosia purpurea . Based on a literature review very few articles have been published on Lanceolatin a.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.6877   -3.7979    1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0356   -2.6006    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -2.5817    0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -3.7130    1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -3.7422    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017   -2.5695    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4763   -2.5347    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1140   -3.6025    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1106   -1.3473    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3914   -0.1847    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053    1.0677   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4559    1.0906   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581    2.2741   -0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137    3.4828   -0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670    3.4800   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4682    2.2904   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976   -0.2841    0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.3724    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9557   -1.3878    0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.2237    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    0.9254   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3620    2.0511   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1697    1.8829   -1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323    1.9670    0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    3.2445   -0.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7785   -3.6780    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407   -4.5628    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142   -4.1888    2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -4.6362    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535   -4.6375    1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770   -1.3438    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987    0.1600   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2033    2.2218   -0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    4.3747   -0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392    4.4195   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4132    2.3292   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8749   -0.2719    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    1.1083   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607    1.2772   -2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    2.8801   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.3407   -1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7586    1.5598    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6922    2.9867    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1726    1.2994    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6846    3.5474    0.6770 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  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 19  3  1  0
 16 11  1  0
 18  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv1652304282201272D          

 25 27  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.1434   -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
    1.4289   -2.4750    0.0000 O   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
    3.5724    1.2375    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
    4.2868   -0.0000    0.0000 C   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
   -1.4289    0.0000    0.0000 O   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
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C=C(OC2=C1\C=C\C(C)(C)O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O4/c1-21(2,23)12-11-16-18(24-3)10-9-15-17(22)13-19(25-20(15)16)14-7-5-4-6-8-14/h4-13,23H,1-3H3/b12-11+

> <INCHI_KEY>
GWHQUBFEZSVTKH-VAWYXSNFSA-N

> <FORMULA>
C21H20O4

> <MOLECULAR_WEIGHT>
336.387

> <EXACT_MASS>
336.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60991641389749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.3494314320000003

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.867524136784244

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.942500192215892

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7955873197852226

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
99.6259

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lanceolatin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24    1   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₄

Average Mass

336.3870 Da

Monoisotopic Mass

336.13616 Da

IUPAC Name

8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

lanceolatin A

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C=C(OC2=C1\C=C\C(C)(C)O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H20O4/c1-21(2,23)12-11-16-18(24-3)10-9-15-17(22)13-19(25-20(15)16)14-7-5-4-6-8-14/h4-13,23H,1-3H3/b12-11+

InChI Key

GWHQUBFEZSVTKH-VAWYXSNFSA-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
Tephrosia apollinea	Plant	KNApSAcK
Tephrosia lanceolata	Plant	KNApSAcK
Tephrosia purpurea	Plant	KNApSAcK

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

7-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
Cinnamyl alcohol
1-benzopyran
Anisole
Phenol ether
Styrene
Alkyl aryl ether
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110019 )

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	3.92	ALOGPS
logP	3.35	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.94	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.63 m³·mol⁻¹	ChemAxon
Polarizability	36.61 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

Not Available

KNApSAcK ID

C00004010

Chemspider ID

4946473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lanceolatin A(flavonoid) (NP0052401)

MOL for NP0052401 (Lanceolatin A(flavonoid))

3D MOL for NP0052401 (Lanceolatin A(flavonoid))

3D SDF for NP0052401 (Lanceolatin A(flavonoid))

3D-SDF for NP0052401 (Lanceolatin A(flavonoid))

PDB for NP0052401 (Lanceolatin A(flavonoid))

3D PDB for NP0052401 (Lanceolatin A(flavonoid))

SMILES for NP0052401 (Lanceolatin A(flavonoid))

INCHI for NP0052401 (Lanceolatin A(flavonoid))

Structure for NP0052401 (Lanceolatin A(flavonoid))

3D Structure for NP0052401 (Lanceolatin A(flavonoid))