NP-MRD: Showing NP-Card for 1-chloro-(1-deoxo-10,11-dihydro)huperzinine (NP0043584)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-21 00:57:03 UTC

Updated at

2021-06-30 00:19:21 UTC

NP-MRD ID

NP0043584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-chloro-(1-deoxo-10,11-dihydro)huperzinine

Provided By

JEOL Database JEOL Logo

Description

(1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0²,⁷]Trideca-2(7),3,5,10-tetraen-1-amine belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom. 1-chloro-(1-deoxo-10,11-dihydro)huperzinine is found in Lycopodiastrum casuarinoides. 1-chloro-(1-deoxo-10,11-dihydro)huperzinine was first documented in 2013 (Tang, Y., et al.). Based on a literature review very few articles have been published on (1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0²,⁷]Trideca-2(7),3,5,10-tetraen-1-amine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102573D          

 41 43  0  0  0  0            999 V2000
   -0.2218   -0.8577   -4.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.3703   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.2560   -2.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0905   -2.6223   -1.9132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1039   -2.5372   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.5886    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.5192    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -0.5180    0.1650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2357   -0.7561   -0.8246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0468    0.5148   -0.9148 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3204    1.6921   -1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    0.4153   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8866   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.5986    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.6128    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -3.8975    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -5.2120    1.7389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -4.2358    0.0645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.2369   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -3.6900   -1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6999   -0.3165   -4.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.9728   -5.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.9046   -3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.5395   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337   -2.9359   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -3.3071   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.3110    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -1.6235    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952   -0.5578    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -0.3825    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.4017   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    1.5429   -2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.0033   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    2.5582   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    0.5084   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714    1.2328   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -0.5058   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.5751    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.3982    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -4.6084   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -3.9635   -2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  9  8  1  0  0  0  0
  9 13  1  0  0  0  0
  3 24  1  6  0  0  0
 19 20  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
 20  4  1  0  0  0  0
  6  7  1  0  0  0  0
  9  3  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  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 18  2  0  0  0  0
  9 10  1  6  0  0  0
  3  2  1  0  0  0  0
  2  1  2  3  0  0  0
 11 10  1  0  0  0  0
 10 12  1  0  0  0  0
  4  5  1  0  0  0  0
 16 17  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
  4 25  1  6  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
  5 26  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  2 23  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2218   -0.8577   -4.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.3703   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.2560   -2.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0905   -2.6223   -1.9132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1039   -2.5372   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.5886    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.5192    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -0.5180    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -0.7561   -0.8246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0468    0.5148   -0.9148 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    1.6921   -1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    0.4153   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8866   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.5986    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.6128    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -3.8975    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -5.2120    1.7389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -4.2358    0.0645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.2369   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -3.6900   -1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999   -0.3165   -4.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.9728   -5.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.9046   -3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.5395   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337   -2.9359   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -3.3071   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.3110    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -1.6235    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952   -0.5578    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -0.3825    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.4017   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    1.5429   -2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.0033   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    2.5582   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    0.5084   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714    1.2328   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -0.5058   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.5751    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.3982    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -4.6084   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -3.9635   -2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  9  8  1  0
  9 13  1  0
  3 24  1  6
 19 20  1  0
  5  6  2  0
  6  8  1  0
 20  4  1  0
  6  7  1  0
  9  3  1  0
 19 13  2  0
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  2  0
  9 10  1  6
  3  2  1  0
  2  1  2  3
 11 10  1  0
 10 12  1  0
  4  5  1  0
 16 17  1  0
 20 40  1  0
 20 41  1  0
  4 25  1  6
 14 38  1  0
 15 39  1  0
  5 26  1  0
  8 30  1  0
  8 31  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
M  END


  Mrv1652306212102573D          

 41 43  0  0  0  0            999 V2000
   -0.2218   -0.8577   -4.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.3703   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.2560   -2.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0905   -2.6223   -1.9132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1039   -2.5372   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.5886    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.5192    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -0.5180    0.1650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2357   -0.7561   -0.8246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0468    0.5148   -0.9148 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3204    1.6921   -1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    0.4153   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8866   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.5986    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.6128    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -3.8975    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -5.2120    1.7389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -4.2358    0.0645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.2369   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -3.6900   -1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6999   -0.3165   -4.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.9728   -5.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.9046   -3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.5395   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337   -2.9359   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -3.3071   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.3110    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -1.6235    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952   -0.5578    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -0.3825    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.4017   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    1.5429   -2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.0033   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    2.5582   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    0.5084   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714    1.2328   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -0.5058   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.5751    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.3982    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -4.6084   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -3.9635   -2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  9  8  1  0  0  0  0
  9 13  1  0  0  0  0
  3 24  1  6  0  0  0
 19 20  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
 20  4  1  0  0  0  0
  6  7  1  0  0  0  0
  9  3  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  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 18  2  0  0  0  0
  9 10  1  6  0  0  0
  3  2  1  0  0  0  0
  2  1  2  3  0  0  0
 11 10  1  0  0  0  0
 10 12  1  0  0  0  0
  4  5  1  0  0  0  0
 16 17  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
  4 25  1  6  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
  5 26  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  2 23  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])[C@]1([H])[C@@]2([H])C([H])=C(C([H])([H])[H])C([H])([H])[C@]1(N(C([H])([H])[H])C([H])([H])[H])C1=C(N=C(Cl)C([H])=C1[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H21ClN2/c1-5-13-12-8-11(2)10-17(13,20(3)4)14-6-7-16(18)19-15(14)9-12/h5-8,12-13H,1,9-10H2,2-4H3/t12-,13+,17+/m0/s1

> <INCHI_KEY>
QYMWDGVSRSEZKZ-OGHNNQOOSA-N

> <FORMULA>
C17H21ClN2

> <MOLECULAR_WEIGHT>
288.82

> <EXACT_MASS>
288.1393264

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.26229858961398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-1-amine

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.3972862543333333

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.220511283940667

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
86.49180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2218   -0.8577   -4.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.3703   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.2560   -2.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0905   -2.6223   -1.9132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1039   -2.5372   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.5886    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.5192    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -0.5180    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -0.7561   -0.8246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0468    0.5148   -0.9148 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    1.6921   -1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    0.4153   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8866   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.5986    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.6128    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -3.8975    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -5.2120    1.7389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -4.2358    0.0645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.2369   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -3.6900   -1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999   -0.3165   -4.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.9728   -5.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.9046   -3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.5395   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337   -2.9359   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -3.3071   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.3110    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -1.6235    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952   -0.5578    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -0.3825    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.4017   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    1.5429   -2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.0033   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    2.5582   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    0.5084   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714    1.2328   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -0.5058   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.5751    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.3982    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -4.6084   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -3.9635   -2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  9  8  1  0
  9 13  1  0
  3 24  1  6
 19 20  1  0
  5  6  2  0
  6  8  1  0
 20  4  1  0
  6  7  1  0
  9  3  1  0
 19 13  2  0
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  2  0
  9 10  1  6
  3  2  1  0
  2  1  2  3
 11 10  1  0
 10 12  1  0
  4  5  1  0
 16 17  1  0
 20 40  1  0
 20 41  1  0
  4 25  1  6
 14 38  1  0
 15 39  1  0
  5 26  1  0
  8 30  1  0
  8 31  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.222  -0.858  -4.599  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.507  -1.370  -3.394  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.407  -1.256  -2.183  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.091  -2.622  -1.913  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -2.537  -0.792  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.063  -1.589   0.158  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.072  -1.519   1.267  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.987  -0.518   0.165  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.236  -0.756  -0.825  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.047   0.515  -0.915  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.320   1.692  -1.398  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.309   0.415  -1.658  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.069  -1.887  -0.150  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.945  -1.599   0.915  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.675  -2.613   1.524  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.495  -3.898   1.057  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -3.360  -5.212   1.739  0.00  0.00          Cl+0
HETATM   18  N   UNK     0      -1.650  -4.236   0.065  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.932  -3.237  -0.511  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.043  -3.690  -1.570  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.700  -0.317  -4.790  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.914  -0.973  -5.429  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.447  -1.905  -3.270  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.199  -0.540  -2.451  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.634  -2.936  -2.815  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.873  -3.307  -0.768  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.824  -2.311   1.188  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.577  -1.624   2.237  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.595  -0.558   1.243  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.617  -0.383   1.190  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.520   0.402  -0.096  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.112   1.543  -2.393  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.468   2.003  -0.710  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.992   2.558  -1.459  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.178   0.508  -2.740  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.971   1.233  -1.348  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.863  -0.506  -1.459  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.064  -0.575   1.265  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.360  -2.398   2.335  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.539  -4.608  -1.229  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.530  -3.963  -2.464  0.00  0.00           H+0
CONECT    1    2   21   22                                                  
CONECT    2    3    1   23                                                  
CONECT    3    4   24    9    2                                             
CONECT    4    3   20    5   25                                             
CONECT    5    6    4   26                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6   27   28   29                                             
CONECT    8    9    6   30   31                                             
CONECT    9    8   13    3   10                                             
CONECT   10    9   11   12                                                  
CONECT   11   10   32   33   34                                             
CONECT   12   10   35   36   37                                             
CONECT   13    9   19   14                                                  
CONECT   14   13   15   38                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   19   16                                                       
CONECT   19   20   13   18                                                  
CONECT   20   19    4   40   41                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2218   -0.8577   -4.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.3703   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.2560   -2.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0905   -2.6223   -1.9132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1039   -2.5372   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.5886    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.5192    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -0.5180    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -0.7561   -0.8246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0468    0.5148   -0.9148 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    1.6921   -1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    0.4153   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8866   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.5986    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.6128    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -3.8975    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -5.2120    1.7389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -4.2358    0.0645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.2369   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -3.6900   -1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999   -0.3165   -4.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.9728   -5.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.9046   -3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.5395   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337   -2.9359   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -3.3071   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.3110    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -1.6235    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952   -0.5578    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -0.3825    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.4017   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    1.5429   -2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.0033   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    2.5582   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    0.5084   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714    1.2328   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -0.5058   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.5751    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.3982    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -4.6084   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -3.9635   -2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  9  8  1  0
  9 13  1  0
  3 24  1  6
 19 20  1  0
  5  6  2  0
  6  8  1  0
 20  4  1  0
  6  7  1  0
  9  3  1  0
 19 13  2  0
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  2  0
  9 10  1  6
  3  2  1  0
  2  1  2  3
 11 10  1  0
 10 12  1  0
  4  5  1  0
 16 17  1  0
 20 40  1  0
 20 41  1  0
  4 25  1  6
 14 38  1  0
 15 39  1  0
  5 26  1  0
  8 30  1  0
  8 31  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁ClN₂

Average Mass

288.8200 Da

Monoisotopic Mass

288.13933 Da

IUPAC Name

(1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-1-amine

Traditional Name

(1R,9R,13R)-5-chloro-13-ethenyl-N,N,11-trimethyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-1-amine

CAS Registry Number

Not Available

SMILES

[H]C([H])=C([H])[C@]1([H])[C@@]2([H])C([H])=C(C([H])([H])[H])C([H])([H])[C@]1(N(C([H])([H])[H])C([H])([H])[H])C1=C(N=C(Cl)C([H])=C1[H])C2([H])[H]

InChI Identifier

InChI=1S/C17H21ClN2/c1-5-13-12-8-11(2)10-17(13,20(3)4)14-6-7-16(18)19-15(14)9-12/h5-8,12-13H,1,9-10H2,2-4H3/t12-,13+,17+/m0/s1

InChI Key

QYMWDGVSRSEZKZ-OGHNNQOOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lycopodiastrum casuarinoides	JEOL database	Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Halopyridines

Direct Parent

2-halopyridines

Alternative Parents

Substituents

2-halopyridine
Aralkylamine
Aryl halide
Aryl chloride
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
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	3.46	ALOGPS
logP	3.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.49 m³·mol⁻¹	ChemAxon
Polarizability	32.26 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

72193488

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang, Y., et al. (2013). Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013). J. Nat. Prod..

Showing NP-Card for 1-chloro-(1-deoxo-10,11-dihydro)huperzinine (NP0043584)

MOL for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

3D MOL for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

3D SDF for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

3D-SDF for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

PDB for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

3D PDB for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

SMILES for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

INCHI for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

Structure for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)

3D Structure for NP0043584 (1-chloro-(1-deoxo-10,11-dihydro)huperzinine)