NP-MRD: Showing NP-Card for Colchiethanamine (NP0069729)

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Record Information

Version

2.0

Created at

2022-04-28 15:04:54 UTC

Updated at

2022-04-28 15:04:55 UTC

NP-MRD ID

NP0069729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Colchiethanamine

Description

(+)-Colchiethanamine belongs to the class of organic compounds known as phenethylisoquinoline alkaloids. These are alkaloids with a structure based on the phenethylisoquinoline skeleton. Phenethylisoquinoline is a tricyclic compound that consists of a quinoline that is carries a phenethyl group at the 2-position. Colchiethanamine is found in Colchicum szovitsii. Colchiethanamine was first documented in 2012 (PMID: 23176065). Based on a literature review very few articles have been published on (+)-Colchiethanamine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -4.2591    2.8153   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3629    1.6359   -1.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307    0.5668   -1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5678    0.6352   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085   -0.4124    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8437   -1.5338   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -1.6071   -1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6634   -0.5559   -1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286   -0.6380   -2.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -2.6900   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4094   -2.8093    0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162   -1.6877    1.8340 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910   -1.7271    2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6629   -0.3974    1.2857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5939    0.3043    0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093   -0.3768   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.4943   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    0.3456    0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8882    1.1431    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8365    2.1191   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    2.9193   -1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    2.2696   -1.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5827    1.4763   -1.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8664    3.6327   -0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    3.1406   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103    2.6183    0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527    1.5182    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141   -2.4919   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7415   -1.4395   -3.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1249   -2.6367   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -3.6298   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -3.6371    1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -3.2659    0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084   -2.2731    2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -2.2918    3.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -0.7267    3.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.2427    2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    1.3377    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081    0.4288    1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -1.3694    0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -0.3765   -1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8560   -0.4034    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    1.0140    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9357    3.6376   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682    3.0540   -2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    1.6278   -1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 14  5  1  0
  5  4  2  0
  4  3  1  0
  5  6  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 29  1  0
  7 28  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
  4 27  1  0
M  END


  Mrv1652304282217042D          

 23 25  0  0  1  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
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   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
    2.8579   -0.0000    0.0000 C   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  6  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  2 21  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2CCN(C)[C@@H](CCC3=CC=C(O)C=C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO3/c1-20-10-9-14-11-18(22)19(23-2)12-16(14)17(20)8-5-13-3-6-15(21)7-4-13/h3-4,6-7,11-12,17,21-22H,5,8-10H2,1-2H3/t17-/m0/s1

> <INCHI_KEY>
IVZAZZKOQHAJCF-KRWDZBQOSA-N

> <FORMULA>
C19H23NO3

> <MOLECULAR_WEIGHT>
313.397

> <EXACT_MASS>
313.167793605

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.037277079967055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

> <JCHEM_LOGP>
3.5492644840357364

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.472737193175512

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.821735779552483

> <JCHEM_PKA_STRONGEST_BASIC>
8.35053007006225

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
91.97410000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-ol

> <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       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21    2                                                            
CONECT   22    1   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₃

Average Mass

313.3970 Da

Monoisotopic Mass

313.16779 Da

IUPAC Name

(1S)-1-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

Traditional Name

(1S)-1-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-ol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2CCN(C)[C@@H](CCC3=CC=C(O)C=C3)C2=C1

InChI Identifier

InChI=1S/C19H23NO3/c1-20-10-9-14-11-18(22)19(23-2)12-16(14)17(20)8-5-13-3-6-15(21)7-4-13/h3-4,6-7,11-12,17,21-22H,5,8-10H2,1-2H3/t17-/m0/s1

InChI Key

IVZAZZKOQHAJCF-KRWDZBQOSA-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
Colchicum szovitsii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylisoquinoline alkaloids. These are alkaloids with a structure based on the phenethylisoquinoline skeleton. Phenethylisoquinoline is a tricyclic compound that consists of a quinoline that is carries a phenethyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Phenethylisoquinoline alkaloids

Sub Class

Not Available

Direct Parent

Phenethylisoquinoline alkaloids

Alternative Parents

Substituents

Phenethylisoquinoline alkaloid
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
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	3.55	ChemAxon
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	8.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.97 m³·mol⁻¹	ChemAxon
Polarizability	35.04 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

30856091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14655880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Reddy RJ, Kawai N, Uenishi J: Synthesis of the 1-phenethyltetrahydroisoquinoline alkaloids (+)-dysoxyline, (+)-colchiethanamine, and (+)-colchiethine. J Org Chem. 2012 Dec 21;77(24):11101-8. doi: 10.1021/jo302157e. Epub 2012 Dec 6. [PubMed:23176065 ]

Showing NP-Card for Colchiethanamine (NP0069729)

MOL for NP0069729 (Colchiethanamine)

3D MOL for NP0069729 (Colchiethanamine)

3D SDF for NP0069729 (Colchiethanamine)

3D-SDF for NP0069729 (Colchiethanamine)

PDB for NP0069729 (Colchiethanamine)

3D PDB for NP0069729 (Colchiethanamine)

SMILES for NP0069729 (Colchiethanamine)

INCHI for NP0069729 (Colchiethanamine)

Structure for NP0069729 (Colchiethanamine)

3D Structure for NP0069729 (Colchiethanamine)