NP-MRD: Showing NP-Card for Huperzine A (NP0013517)

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Record Information

Version

2.0

Created at

2021-01-05 22:51:20 UTC

Updated at

2021-07-15 17:14:41 UTC

NP-MRD ID

NP0013517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Huperzine A

Provided By

NPAtlas

Description

Huperzine A belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. Huperzine A is found in Huperzia selago, Huperzia serrata , Huperzia varium, Paecilomyces, Paecilomyces tenuis, Phlegmariurus phlegmaria, Phlegmariurus tetrastichus and Phlegmariurus varius. Huperzine A was first documented in 2015 (PMID: 25427833). Based on a literature review very few articles have been published on Huperzine A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119363D          

 36 38  0  0  0  0            999 V2000
    3.6267   -0.0145    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.5457   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.5351   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.1333   -1.4952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4844    2.1216   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    1.8818    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.3801    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.1215    1.3101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6378   -0.0242    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5358   -0.4499    1.7253 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3118   -1.0279    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -2.0608    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.9884    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.8989   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -3.7551   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.9122   -1.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.9638   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.0462   -2.0686 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4431   -1.0956    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.4995    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.1080   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.0004   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.6384   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    3.0150   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.9278    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    3.0914   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9754    1.5112    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.8293    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.7576    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.4428    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016    0.1868    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0967    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -3.8080    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.8884   -2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.5266   -2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -0.4300   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  3  1  0  0  0  0
 17 11  2  0  0  0  0
 18  4  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  4 23  1  6  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    3.6267   -0.0145    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.5457   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.5351   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.1333   -1.4952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4844    2.1216   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    1.8818    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.3801    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.1215    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.0242    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5358   -0.4499    1.7253 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118   -1.0279    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -2.0608    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.9884    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.8989   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -3.7551   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.9122   -1.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.9638   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.0462   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431   -1.0956    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.4995    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.1080   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.0004   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.6384   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    3.0150   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.9278    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    3.0914   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9754    1.5112    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.8293    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.7576    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.4428    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016    0.1868    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0967    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -3.8080    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.8884   -2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.5266   -2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -0.4300   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  9  3  1  0
 17 11  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  6
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
M  END


  Mrv1652306242119363D          

 36 38  0  0  0  0            999 V2000
    3.6267   -0.0145    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.5457   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.5351   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.1333   -1.4952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4844    2.1216   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    1.8818    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.3801    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.1215    1.3101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6378   -0.0242    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5358   -0.4499    1.7253 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3118   -1.0279    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -2.0608    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.9884    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.8989   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -3.7551   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.9122   -1.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.9638   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.0462   -2.0686 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4431   -1.0956    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.4995    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.1080   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.0004   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.6384   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    3.0150   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.9278    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    3.0914   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9754    1.5112    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.8293    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.7576    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.4428    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016    0.1868    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0967    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -3.8080    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.8884   -2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.5266   -2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -0.4300   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  3  1  0  0  0  0
 17 11  2  0  0  0  0
 18  4  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  4 23  1  6  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])[C@@]12C3=C(N([H])C(=O)C([H])=C3[H])C([H])([H])[C@@]([H])(C([H])=C(C([H])([H])[H])C1([H])[H])\C2=C(/[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3-/t10-,15+/m1/s1

> <INCHI_KEY>
ZRJBHWIHUMBLCN-UHFFFAOYSA-N

> <FORMULA>
C15H18N2O

> <MOLECULAR_WEIGHT>
242.322

> <EXACT_MASS>
242.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.7821231228327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,13Z)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
0.6177157886666669

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.107823071185413

> <JCHEM_PKA_STRONGEST_BASIC>
9.093326822285933

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
75.79499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,13Z)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    3.6267   -0.0145    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.5457   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.5351   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.1333   -1.4952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4844    2.1216   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    1.8818    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.3801    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.1215    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.0242    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5358   -0.4499    1.7253 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118   -1.0279    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -2.0608    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.9884    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.8989   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -3.7551   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.9122   -1.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.9638   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.0462   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431   -1.0956    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.4995    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.1080   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.0004   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.6384   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    3.0150   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.9278    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    3.0914   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9754    1.5112    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.8293    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.7576    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.4428    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016    0.1868    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0967    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -3.8080    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.8884   -2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.5266   -2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -0.4300   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  9  3  1  0
 17 11  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  6
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.627  -0.015   0.298  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.648   0.546  -0.655  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.356   0.535  -0.464  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.415   1.133  -1.495  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.484   2.122  -0.862  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.953   1.882   0.335  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.294   2.380   0.736  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.168   1.121   1.310  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.638  -0.024   0.710  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.536  -0.450   1.725  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.312  -1.028   0.235  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.754  -2.061   1.050  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.635  -2.988   0.605  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.094  -2.899  -0.675  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.923  -3.755  -1.124  0.00  0.00           O+0
HETATM   16  N   UNK     0      -1.683  -1.912  -1.480  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.791  -0.964  -1.048  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.450   0.046  -2.069  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.443  -1.096   0.501  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.645   0.500   1.278  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.660   0.108  -0.105  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.018   1.000  -1.582  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.033   1.638  -2.267  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.734   3.015  -1.404  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.269   2.928   1.708  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.717   3.091  -0.003  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.975   1.511   0.906  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.609   1.829   1.725  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.814   0.758   2.142  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.557  -1.443   1.943  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.602   0.187   2.547  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.373  -2.097   2.042  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.996  -3.808   1.227  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.070  -1.888  -2.465  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.393   0.527  -2.424  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.096  -0.430  -2.906  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   22                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   18   23                                             
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   25   26   27                                             
CONECT    8    6    9   28   29                                             
CONECT    9    8   10   11    3                                             
CONECT   10    9   30   31                                                  
CONECT   11    9   12   17                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   34                                                  
CONECT   17   16   18   11                                                  
CONECT   18   17    4   35   36                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   18                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
    3.6267   -0.0145    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.5457   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.5351   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.1333   -1.4952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4844    2.1216   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    1.8818    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.3801    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.1215    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.0242    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5358   -0.4499    1.7253 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118   -1.0279    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -2.0608    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.9884    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.8989   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -3.7551   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.9122   -1.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.9638   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.0462   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431   -1.0956    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.4995    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.1080   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.0004   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.6384   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    3.0150   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.9278    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    3.0914   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9754    1.5112    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.8293    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.7576    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.4428    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016    0.1868    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0967    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -3.8080    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.8884   -2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.5266   -2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -0.4300   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  9  3  1  0
 17 11  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  6
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Huperzine a, (5alpha,9beta,11Z)-(-)-isomer	MeSH

Chemical Formula

C₁₅H₁₈N₂O

Average Mass

242.3220 Da

Monoisotopic Mass

242.14191 Da

IUPAC Name

(1S,9S,13Z)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

Traditional Name

(1S,9S,13Z)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

CAS Registry Number

Not Available

SMILES

CC=C1C2CC3=C(C=CC(=O)N3)C1(N)CC(C)=C2

InChI Identifier

InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)

InChI Key

ZRJBHWIHUMBLCN-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, 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
Huperzia selago	Plant	KNApSAcK
Huperzia serrata	Plant	KNApSAcK
Huperzia varium	Plant	KNApSAcK
Paecilomyces	NPAtlas	25427833
Paecilomyces tenuis	LOTUS Database	35616633
Phlegmariurus phlegmaria	LOTUS Database	35616633
Phlegmariurus tetrastichus	LOTUS Database	35616633
Phlegmariurus varius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Quinolones and derivatives

Alternative Parents

Substituents

Quinolone
Pyridinone
Aralkylamine
Pyridine
Heteroaromatic compound
Lactam
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen 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	1.78	ALOGPS
logP	0.62	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.8 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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

NPAtlas ID

NPA000438

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027768

Chemspider ID

1215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Huperzine A

METLIN ID

Not Available

PubChem Compound

1253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Su J, Yang M: Huperzine A production by Paecilomyces tenuis YS-13, an endophytic fungus isolated from Huperzia serrata. Nat Prod Res. 2015;29(11):1035-41. doi: 10.1080/14786419.2014.980245. Epub 2014 Nov 27. [PubMed:25427833 ]

Showing NP-Card for Huperzine A (NP0013517)

MOL for NP0013517 (Huperzine A)

3D MOL for NP0013517 (Huperzine A)

3D SDF for NP0013517 (Huperzine A)

3D-SDF for NP0013517 (Huperzine A)

PDB for NP0013517 (Huperzine A)

3D PDB for NP0013517 (Huperzine A)

SMILES for NP0013517 (Huperzine A)

INCHI for NP0013517 (Huperzine A)

Structure for NP0013517 (Huperzine A)

3D Structure for NP0013517 (Huperzine A)