NP-MRD: Showing NP-Card for Proscillaridin A (NP0085993)

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Record Information

Version

2.0

Created at

2022-04-29 06:23:51 UTC

Updated at

2022-04-29 06:23:51 UTC

NP-MRD ID

NP0085993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Proscillaridin A

Description

Proscillaridin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Proscillaridin A is found in Drimia indica, Drimia maritima and Scilla bifolia . Proscillaridin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221603222D          

 47 52  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1572004221603222D          

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    3.4830    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0469    2.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041   -2.2057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6360   -1.5750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3557   -0.7991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5435   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4594    3.5719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844   -2.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481   -1.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875   -0.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5723   -2.8364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9163   -2.3509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238   -1.4298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1678   -0.9443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0754   -0.0231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 16  1  1  6  0  0  0
 17  4  1  0  0  0  0
 17 15  2  0  0  0  0
 18  5  1  0  0  0  0
 18 14  2  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 17  1  6  0  0  0
 21  9  1  0  0  0  0
 22  6  1  0  0  0  0
 22 21  1  0  0  0  0
 23  7  1  0  0  0  0
 24 16  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28  2  1  6  0  0  0
 28 11  1  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
 29  3  1  6  0  0  0
 29 12  1  0  0  0  0
 29 20  1  0  0  0  0
 30 13  1  0  0  0  0
 30 22  1  0  0  0  0
 30 29  1  0  0  0  0
 31 23  2  0  0  0  0
 24 32  1  1  0  0  0
 25 33  1  1  0  0  0
 26 34  1  6  0  0  0
 30 35  1  6  0  0  0
 36 15  1  0  0  0  0
 36 23  1  0  0  0  0
 37 16  1  0  0  0  0
 37 27  1  0  0  0  0
 19 38  1  6  0  0  0
 27 38  1  1  0  0  0
 16 39  1  1  0  0  0
 19 40  1  1  0  0  0
 20 41  1  1  0  0  0
 21 42  1  1  0  0  0
 22 43  1  6  0  0  0
 24 44  1  6  0  0  0
 25 45  1  1  0  0  0
 26 46  1  1  0  0  0
 27 47  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0085993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2(O)[C@]3([H])CCC4=C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1

> <INCHI_KEY>
MYEJFUXQJGHEQK-ALRJYLEOSA-N

> <FORMULA>
C30H42O8

> <MOLECULAR_WEIGHT>
530.658

> <EXACT_MASS>
530.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.25788771805379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.303163803333332

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.272368886950634

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.22389822822514

> <JCHEM_PKA_STRONGEST_BASIC>
0.2957971495471319

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
140.0543

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proscillaridin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      12.619  -5.024   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.613   5.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.612  -3.846   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.088   5.452   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.128  -4.117   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.120  -2.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.597  -1.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.081  -1.221   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.858   6.667   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.651  -5.566   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.636  -3.211   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.590  -0.314   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.355  -1.089   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.493   4.025   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      13.089  -2.398   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   39  H   UNK     0      14.135  -5.295   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      12.565  -0.949   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.411   1.514   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       8.017  -0.136   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      16.644  -4.388   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      14.605  -2.669   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      17.113  -1.763   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      15.074  -0.043   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   28                                                            
CONECT    3   29                                                            
CONECT    4    7   17                                                       
CONECT    5    6   18                                                       
CONECT    6    5   22                                                       
CONECT    7    4   23                                                       
CONECT    8   11   19                                                       
CONECT    9   12   21                                                       
CONECT   10   13   20                                                       
CONECT   11    8   28                                                       
CONECT   12    9   29                                                       
CONECT   13   10   30                                                       
CONECT   14   18   19                                                       
CONECT   15   17   36                                                       
CONECT   16    1   24   37   39                                             
CONECT   17    4   15   20                                                  
CONECT   18    5   14   28                                                  
CONECT   19    8   14   38   40                                             
CONECT   20   10   17   29   41                                             
CONECT   21    9   22   28   42                                             
CONECT   22    6   21   30   43                                             
CONECT   23    7   31   36                                                  
CONECT   24   16   25   32   44                                             
CONECT   25   24   26   33   45                                             
CONECT   26   25   27   34   46                                             
CONECT   27   26   37   38   47                                             
CONECT   28    2   11   18   21                                             
CONECT   29    3   12   20   30                                             
CONECT   30   13   22   29   35                                             
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   30                                                            
CONECT   36   15   23                                                       
CONECT   37   16   27                                                       
CONECT   38   19   27                                                       
CONECT   39   16                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
a-32686Proscillaridin	ChEMBL
2936Tradenal	ChEMBL
Abbott brand OF proscillaridin	MeSH
Knoll brand OF proscillaridin	MeSH
Proscillaridin	MeSH
Desglucotransvaaline	MeSH
Caradrin	MeSH
Digitalysat	MeSH
Rhamnoside, scillarenin	MeSH
Talusin	MeSH
Proscillaridin a	MeSH
Sandoscill	MeSH
Scillarenin rhamnoside	MeSH
Scillase	MeSH
Ysatfabrik brand OF proscillaridin	MeSH
Ziethen brand OF proscillaridin	MeSH
a, Proscillaridin	MeSH
Proscillaridine	MeSH

Chemical Formula

C₃₀H₄₂O₈

Average Mass

530.6580 Da

Monoisotopic Mass

530.28797 Da

IUPAC Name

5-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2H-pyran-2-one

Traditional Name

proscillaridin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CCC4=C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1

InChI Key

MYEJFUXQJGHEQK-ALRJYLEOSA-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
Drimia indica	LOTUS Database	35616633
Drimia maritima	LOTUS Database	35616633
Scilla bifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroidal glycoside
14-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranone
Pyran
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Secondary alcohol
Lactone
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
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
logP	2.37	ALOGPS
logP	2.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.05 m³·mol⁻¹	ChemAxon
Polarizability	58.26 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13307

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Proscillaridin

METLIN ID

Not Available

PubChem Compound

5284613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Proscillaridin A (NP0085993)

MOL for NP0085993 (Proscillaridin A)

3D MOL for NP0085993 (Proscillaridin A)

3D SDF for NP0085993 (Proscillaridin A)

3D-SDF for NP0085993 (Proscillaridin A)

PDB for NP0085993 (Proscillaridin A)

3D PDB for NP0085993 (Proscillaridin A)

SMILES for NP0085993 (Proscillaridin A)

INCHI for NP0085993 (Proscillaridin A)

Structure for NP0085993 (Proscillaridin A)

3D Structure for NP0085993 (Proscillaridin A)