NP-MRD: Showing NP-Card for 16alpha-Acetoxycalactin (NP0070717)

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Record Information

Version

2.0

Created at

2022-04-28 16:10:17 UTC

Updated at

2022-04-28 16:10:17 UTC

NP-MRD ID

NP0070717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16alpha-Acetoxycalactin

Description

16Alpha-acetoxycalactin belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Thus, 16alpha-acetoxycalactin is considered to be a sterol. 16alpha-Acetoxycalactin is found in Asclepias curassavica L. . Based on a literature review very few articles have been published on 16alpha-acetoxycalactin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218102D          

 42 48  0  0  1  0            999 V2000
    7.0989    2.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2583    1.2563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.9162    2.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5 41  1  6  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282218102D          

 42 48  0  0  1  0            999 V2000
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    1.1720    2.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    2.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684    2.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6152    1.3873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0104    0.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    1.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913    0.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    2.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892    2.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6487    3.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    4.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    4.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3233    3.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    2.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    0.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334    2.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    2.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375    2.5991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390    0.9896    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  6  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  6  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 21 37  1  6  0  0  0
 20 38  1  6  0  0  0
 14 39  1  6  0  0  0
 39 40  2  0  0  0  0
  5 41  1  6  0  0  0
  2 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0070717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H]([C@@H](C[C@]54O)OC(C)=O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O11/c1-15-8-24(34)31(37)27(39-15)41-21-10-18-4-5-20-19(29(18,14-32)11-22(21)42-31)6-7-28(3)26(17-9-25(35)38-13-17)23(40-16(2)33)12-30(20,28)36/h9,14-15,18-24,26-27,34,36-37H,4-8,10-13H2,1-3H3/t15-,18+,19+,20-,21-,22-,23-,24-,26+,27+,28-,29-,30+,31+/m1/s1

> <INCHI_KEY>
BMPDNBQADRWROC-UGLGPMQLSA-N

> <FORMULA>
C31H42O11

> <MOLECULAR_WEIGHT>
590.666

> <EXACT_MASS>
590.272712172

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.85274121524268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,20R,22S,23R)-14-formyl-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.0234824666666664

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.460884976390558

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.8184844953213

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2042020763476566

> <JCHEM_POLAR_SURFACE_AREA>
158.04999999999998

> <JCHEM_REFRACTIVITY>
144.224

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,20R,22S,23R)-14-formyl-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate

> <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      13.251   3.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.549   2.345   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.389   1.332   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.932   1.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.634   3.341   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.794   4.354   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.496   5.865   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.177   3.838   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.017   2.825   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.315   1.314   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.772   0.816   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.155   0.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.698   0.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.400   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.560   3.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.943   2.808   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   1.794   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   0.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.538  -0.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.326   2.292   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.028   3.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.188   4.816   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.645   4.319   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.501   3.987   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.148   2.590   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.020   1.542   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.659   2.292   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.157   0.835   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.144  -0.325   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.668   0.537   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.251   5.332   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.780   5.516   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.077   7.027   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.475   7.674   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.732   7.777   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.604   6.729   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.574   5.275   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.464   0.758   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.102   3.821   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.262   4.834   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      10.337   4.852   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      15.006   1.847   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   41                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16   39                                             
CONECT   15   14    9                                                       
CONECT   16   14   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20   17   21   26   38                                             
CONECT   21   20   22   24   37                                             
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   21   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   20                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   31                                                       
CONECT   37   21                                                            
CONECT   38   20                                                            
CONECT   39   14   40                                                       
CONECT   40   39                                                            
CONECT   41    5                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
16a-Acetoxycalactin	Generator
16Α-acetoxycalactin	Generator

Chemical Formula

C₃₁H₄₂O₁₁

Average Mass

590.6660 Da

Monoisotopic Mass

590.27271 Da

IUPAC Name

(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,20R,22S,23R)-14-formyl-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate

Traditional Name

(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,20R,22S,23R)-14-formyl-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H]([C@@H](C[C@]54O)OC(C)=O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

InChI Identifier

InChI=1S/C31H42O11/c1-15-8-24(34)31(37)27(39-15)41-21-10-18-4-5-20-19(29(18,14-32)11-22(21)42-31)6-7-28(3)26(17-9-25(35)38-13-17)23(40-16(2)33)12-30(20,28)36/h9,14-15,18-24,26-27,34,36-37H,4-8,10-13H2,1-3H3/t15-,18+,19+,20-,21-,22-,23-,24-,26+,27+,28-,29-,30+,31+/m1/s1

InChI Key

BMPDNBQADRWROC-UGLGPMQLSA-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
Asclepias curassavica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroid ester
19-oxosteroid
14-hydroxysteroid
Oxosteroid
Hydroxysteroid
Para-dioxane
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.74	ALOGPS
logP	1.02	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	158.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	144.22 m³·mol⁻¹	ChemAxon
Polarizability	61.85 Å³	ChemAxon
Number of Rings	7	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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029403

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

101676752

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 16alpha-Acetoxycalactin (NP0070717)

MOL for NP0070717 (16alpha-Acetoxycalactin)

3D MOL for NP0070717 (16alpha-Acetoxycalactin)

3D SDF for NP0070717 (16alpha-Acetoxycalactin)

3D-SDF for NP0070717 (16alpha-Acetoxycalactin)

PDB for NP0070717 (16alpha-Acetoxycalactin)

3D PDB for NP0070717 (16alpha-Acetoxycalactin)

SMILES for NP0070717 (16alpha-Acetoxycalactin)

INCHI for NP0070717 (16alpha-Acetoxycalactin)

Structure for NP0070717 (16alpha-Acetoxycalactin)

3D Structure for NP0070717 (16alpha-Acetoxycalactin)