NP-MRD: Showing NP-Card for Aucherine (NP0139603)

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Record Information

Version

2.0

Created at

2022-06-29 20:01:58 UTC

Updated at

2022-06-29 20:01:59 UTC

NP-MRD ID

NP0139603

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aucherine

Description

Aucherine belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. Aucherine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    3.5077    1.2041    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    1.6193   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    2.8746    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356    0.5388   -0.2677 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8116    0.9058   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    1.4811   -2.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.6086   -1.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044    1.1274   -0.8582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5344    1.4312    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0027    1.8209    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701    1.1531   -0.2003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7206    0.3060    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -0.8948    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034   -0.9214   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7738   -1.9824    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985   -1.9217   -1.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -2.3181   -1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456   -3.0905   -1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4463   -1.9329   -0.0427 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3176   -3.1516    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.4969    1.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930   -0.7999   -0.5999 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5981   -0.8371   -0.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    0.2532   -0.8684 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5730    1.0175    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5896    2.0673    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3840    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    1.8191   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    3.7096    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    2.7634    1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695    3.1808   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0134    0.4558    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    2.0987   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674    2.2540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790    0.5172    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    1.5619    1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156    2.9176    0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5885    0.0601   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1036    0.7637    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2144   -1.6060    1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298   -3.0134    0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152   -1.9410    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -3.4259   -0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -2.9486    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847   -3.9798    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322   -2.0364    1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334   -0.9307   -1.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9443   -1.7290    0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0990    0.0634   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 22  1  0
 22 23  1  0
 22 19  1  0
 19 20  1  0
 19 21  1  1
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  8 24  1  0
  5  4  1  0
 24 14  1  0
 24 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  1
 22 47  1  6
 23 48  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 15 41  1  0
 15 42  1  0
 13 40  1  0
 12 38  1  0
 12 39  1  0
 10 36  1  0
 10 37  1  0
  9 34  1  0
  9 35  1  0
  8 33  1  6
 24 49  1  6
M  END


  Mrv1533004161519302D          

 24 26  0  0  0  0            999 V2000
    7.4843    2.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7019    2.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370    3.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2491    1.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0370    1.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4238    0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340    0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068    0.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1153   -0.4357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6984   -0.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918    0.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    0.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621    0.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827    1.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731    2.0839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    2.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667    3.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016    2.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841    2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1369    3.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    1.8058    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 14 24  1  0  0  0  0
 17 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139603

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1C(O)C(C)(O)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO6/c1-9(2)12-14(19)17(3,22)16(21)23-8-10-4-6-18-7-5-11(13(10)18)24-15(12)20/h4,9,11-14,19,22H,5-8H2,1-3H3

> <INCHI_KEY>
KPTUMNASMZDHPX-UHFFFAOYSA-N

> <FORMULA>
C17H25NO6

> <MOLECULAR_WEIGHT>
339.388

> <EXACT_MASS>
339.168187529

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.8232143369266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-6-methyl-4-(propan-2-yl)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadec-10-ene-3,7-dione

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.11862303933333329

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.06374849253509

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.624836823307215

> <JCHEM_PKA_STRONGEST_BASIC>
7.081965006505134

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
85.2142

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-4-isopropyl-6-methyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadec-10-ene-3,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      13.971   4.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.510   5.458   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.202   6.967   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.357   4.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.665   2.928   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.136   2.472   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.453   1.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.991   1.681   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.450   0.583   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.279   0.227   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.415  -0.813   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.770  -0.081   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.011   1.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.438   1.862   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.969   1.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.074   2.652   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.990   3.890   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.003   5.430   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.471   5.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.283   4.392   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.744   3.904   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.897   4.925   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.589   6.434   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.130   3.371   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    4   23                                                  
CONECT   23   22                                                            
CONECT   24   20   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₅NO₆

Average Mass

339.3880 Da

Monoisotopic Mass

339.16819 Da

IUPAC Name

5,6-dihydroxy-6-methyl-4-(propan-2-yl)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadec-10-ene-3,7-dione

Traditional Name

5,6-dihydroxy-4-isopropyl-6-methyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadec-10-ene-3,7-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1C(O)C(C)(O)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C17H25NO6/c1-9(2)12-14(19)17(3,22)16(21)23-8-10-4-6-18-7-5-11(13(10)18)24-15(12)20/h4,9,11-14,19,22H,5-8H2,1-3H3

InChI Key

KPTUMNASMZDHPX-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizines

Sub Class

Not Available

Direct Parent

Pyrrolizines

Alternative Parents

Substituents

Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Secondary alcohol
Carboxylic acid ester
1,2-diol
Lactone
Azacycle
Oxacycle
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Amine
Organopnictogen compound
Hydrocarbon derivative
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	0.52	ALOGPS
logP	0.12	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.21 m³·mol⁻¹	ChemAxon
Polarizability	34.82 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

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

180203

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aucherine (NP0139603)

MOL for NP0139603 (Aucherine)

3D MOL for NP0139603 (Aucherine)

3D SDF for NP0139603 (Aucherine)

3D-SDF for NP0139603 (Aucherine)

PDB for NP0139603 (Aucherine)

3D PDB for NP0139603 (Aucherine)

SMILES for NP0139603 (Aucherine)

INCHI for NP0139603 (Aucherine)

Structure for NP0139603 (Aucherine)

3D Structure for NP0139603 (Aucherine)