NP-MRD: Showing NP-Card for (-)-Bacobitacin A (NP0073835)

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Record Information

Version

2.0

Created at

2022-04-28 19:03:30 UTC

Updated at

2022-04-28 19:03:30 UTC

NP-MRD ID

NP0073835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Bacobitacin A

Description

(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (-)-Bacobitacin A is found in Bacopa monnieri . Based on a literature review very few articles have been published on (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221032D          

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M  END

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M  END


  Mrv1652304282221032D          

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    1.0596   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5533   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749   -0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094   -0.3415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    0.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    0.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    1.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5050   -1.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793    0.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5311    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  1  0  0  0  0
 17 29  1  1  0  0  0
 17 30  1  1  0  0  0
 15 31  1  6  0  0  0
 13 32  1  6  0  0  0
 12 33  1  1  0  0  0
  8 34  1  1  0  0  0
  6 35  1  6  0  0  0
  4 36  1  0  0  0  0
 36 37  1  0  0  0  0
  1 37  1  0  0  0  0
 37 38  2  0  0  0  0
 36 39  1  0  0  0  0
 36 40  1  0  0  0  0
  1 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3[C@H](O)C=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19-,21-,24+,25+,29+,30-,31-,32+/m1/s1

> <INCHI_KEY>
SGUCHYFOTGXDTG-DOFUNFASSA-N

> <FORMULA>
C32H44O9

> <MOLECULAR_WEIGHT>
572.695

> <EXACT_MASS>
572.298532997

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.15471009537097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.330459391333334

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.931444410383794

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.022661126541323

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8839254921082915

> <JCHEM_POLAR_SURFACE_AREA>
158.43

> <JCHEM_REFRACTIVITY>
154.05030000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-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      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.964  -2.398   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.613  -4.122   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.073  -1.059   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.599  -0.848   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.124  -0.637   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.704   0.789   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.230   1.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.759   2.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.809  -2.374   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.388   0.677   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.194  -2.425   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.762  -0.535   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.032   4.031   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
CONECT    1    2   37   41                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    3    9   34                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16   33                                             
CONECT   13   12    7   14   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18   29   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
CONECT   29   17                                                            
CONECT   30   17                                                            
CONECT   31   15                                                            
CONECT   32   13                                                            
CONECT   33   12                                                            
CONECT   34    8                                                            
CONECT   35    6                                                            
CONECT   36    4   37   39   40                                             
CONECT   37   36    1   38                                                  
CONECT   38   37                                                            
CONECT   39   36                                                            
CONECT   40   36                                                            
CONECT   41    1                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
(3E,6R)-6-Hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₄O₉

Average Mass

572.6950 Da

Monoisotopic Mass

572.29853 Da

IUPAC Name

(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3[C@H](O)C=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

InChI Identifier

InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19-,21-,24+,25+,29+,30-,31-,32+/m1/s1

InChI Key

SGUCHYFOTGXDTG-DOFUNFASSA-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
Bacopa monnieri	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Triterpenoid
Cucurbitacin skeleton
22-oxosteroid
21-oxosteroid
Steroid ester
20-hydroxysteroid
14-alpha-methylsteroid
7-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
2-hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Delta-1-steroid
Cyclohexenone
Acyloin
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Cyclic alcohol
Alpha-hydroxy ketone
Acryloyl-group
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.77	ALOGPS
logP	2.33	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.02	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	154.05 m³·mol⁻¹	ChemAxon
Polarizability	61.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

162982404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Bacobitacin A (NP0073835)

MOL for NP0073835 ((-)-Bacobitacin A)

3D MOL for NP0073835 ((-)-Bacobitacin A)

3D SDF for NP0073835 ((-)-Bacobitacin A)

3D-SDF for NP0073835 ((-)-Bacobitacin A)

PDB for NP0073835 ((-)-Bacobitacin A)

3D PDB for NP0073835 ((-)-Bacobitacin A)

SMILES for NP0073835 ((-)-Bacobitacin A)

INCHI for NP0073835 ((-)-Bacobitacin A)

Structure for NP0073835 ((-)-Bacobitacin A)

3D Structure for NP0073835 ((-)-Bacobitacin A)