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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 17:12:00 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0242212

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Huperzine A

Description

(-)-Huperzine A, also known as 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. Based on a literature review a significant number of articles have been published on (-)-Huperzine A. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-huperzine a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Huperzine A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0242654
     RDKit          3D
Huperzine A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.1267   -2.6003    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.0080    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2951   -1.0285    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.5158    1.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404   -0.9152    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096   -0.8338   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208   -1.5011   -0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303   -0.1680   -1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087   -0.3138   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -1.0063   -1.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613    1.0586   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.7783   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458    3.0679   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5093    3.6053    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.7795    0.7402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.8921    1.1102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    1.6357    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253    0.9791    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159   -3.3699    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668   -1.8302   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -3.1036   -0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -2.4460    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -1.0152    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517   -1.2416    1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.0267   -1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1902   -1.4106   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -2.5630   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348   -0.6145   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.9063   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -0.6422   -2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -1.6125   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    1.3664   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    3.6251   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    3.3524    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.2856    2.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224    1.4344    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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  0
  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  0
  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

  Mrv0541 04121520532D          

 18 20  0  0  0  0            999 V2000
    2.5091   -0.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613    0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717    0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    0.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4649    0.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -0.0512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    1.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6871    2.5420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304    1.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242212

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C15H18N2O

> <MOLECULAR_WEIGHT>
242.322

> <EXACT_MASS>
242.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.824806967252293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]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>
75.795

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242654
     RDKit          3D
Huperzine A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.1267   -2.6003    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.0080    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2951   -1.0285    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.5158    1.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404   -0.9152    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096   -0.8338   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208   -1.5011   -0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303   -0.1680   -1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087   -0.3138   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -1.0063   -1.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613    1.0586   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.7783   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458    3.0679   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5093    3.6053    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.7795    0.7402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.8921    1.1102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    1.6357    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253    0.9791    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159   -3.3699    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668   -1.8302   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -3.1036   -0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -2.4460    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -1.0152    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517   -1.2416    1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.0267   -1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1902   -1.4106   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -2.5630   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348   -0.6145   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.9063   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -0.6422   -2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -1.6125   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    1.3664   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    3.6251   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    3.3524    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.2856    2.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224    1.4344    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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  0
  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  0
  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                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       4.684  -0.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.781   0.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.747   1.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.635  -0.698   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.171  -0.587   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.179   0.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.069   2.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.344   2.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.729   2.304   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.840   0.768   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.334   0.096   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.565  -0.096   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.905   3.121   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.149   4.745   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.369   3.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.361   1.846   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.471   0.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.177   2.353   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    7    3   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    4                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0242212
HETATM    1  C1  UNL     1      -3.249  -1.305  -0.621  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.473  -0.098  -0.998  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.273   0.186  -0.621  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.609   1.427  -1.070  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.266   2.134   0.230  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.399   1.516   1.400  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.508   2.384   2.604  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.447   0.055   1.607  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.500  -0.692   0.266  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.010  -2.018   0.407  1.00  0.00           N  
HETATM   11  C10 UNL     1       0.944  -0.759  -0.162  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.692  -1.733   0.425  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.021  -1.865   0.094  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.561  -0.999  -0.831  1.00  0.00           C  
HETATM   15  O1  UNL     1       4.797  -1.113  -1.145  1.00  0.00           O  
HETATM   16  N2  UNL     1       2.811  -0.045  -1.399  1.00  0.00           N  
HETATM   17  C14 UNL     1       1.494   0.089  -1.074  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.722   1.154  -1.732  1.00  0.00           C  
HETATM   19  H1  UNL     1      -2.801  -2.174  -1.125  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.278  -1.380   0.485  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.308  -1.196  -0.998  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.990   0.621  -1.672  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.243   2.032  -1.711  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.083   3.143   0.132  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.311   1.827   3.544  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.239   3.196   2.507  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.556   2.774   2.665  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.343  -0.257   2.206  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.435  -0.329   2.148  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.460  -2.655  -0.240  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.807  -2.370   1.371  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.270  -2.434   1.168  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.638  -2.651   0.562  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.253   0.584  -2.087  1.00  0.00           H  
HETATM   35  H17 UNL     1       1.305   2.100  -1.677  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.566   0.851  -2.785  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   22
CONECT    3    4    9
CONECT    4    5   18   23
CONECT    5    6    6   24
CONECT    6    7    8
CONECT    7   25   26   27
CONECT    8    9   28   29
CONECT    9   10   11
CONECT   10   30   31
CONECT   11   12   17   17
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   15   16
CONECT   16   17   34
CONECT   17   18
CONECT   18   35   36
END

HMDB0242654
     RDKit          3D
Huperzine A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.1267   -2.6003    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.0080    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2951   -1.0285    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.5158    1.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404   -0.9152    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096   -0.8338   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208   -1.5011   -0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303   -0.1680   -1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087   -0.3138   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -1.0063   -1.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613    1.0586   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.7783   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458    3.0679   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5093    3.6053    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.7795    0.7402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.8921    1.1102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    1.6357    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253    0.9791    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159   -3.3699    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668   -1.8302   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -3.1036   -0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -2.4460    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -1.0152    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517   -1.2416    1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.0267   -1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1902   -1.4106   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -2.5630   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348   -0.6145   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.9063   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -0.6422   -2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -1.6125   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    1.3664   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    3.6251   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    3.3524    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.2856    2.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224    1.4344    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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  0
  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  0
  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 Stereo Labels

Synonyms

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

Chemical Formula

C₁₅H₁₈N₂O

Average Molecular Weight

242.322

Monoisotopic Molecular Weight

242.141913208

IUPAC Name

1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one

Traditional Name

1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	26.82 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	165.796	30932474
DeepCCS	[M-H]-	163.438	30932474
DeepCCS	[M-2H]-	196.324	30932474
DeepCCS	[M+Na]+	171.889	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Huperzine A (HupA),1TMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2291.7	Semi standard non polar	33892256
(-)-Huperzine A (HupA),1TMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2417.3	Standard non polar	33892256
(-)-Huperzine A (HupA),1TMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2738.9	Standard polar	33892256
(-)-Huperzine A (HupA),1TMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2363.2	Semi standard non polar	33892256
(-)-Huperzine A (HupA),1TMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2375.6	Standard non polar	33892256
(-)-Huperzine A (HupA),1TMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2813.0	Standard polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2321.6	Semi standard non polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2561.6	Standard non polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2799.8	Standard polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2367.6	Semi standard non polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2463.1	Standard non polar	33892256
(-)-Huperzine A (HupA),2TMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2668.6	Standard polar	33892256
(-)-Huperzine A (HupA),3TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2410.8	Semi standard non polar	33892256
(-)-Huperzine A (HupA),3TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2612.2	Standard non polar	33892256
(-)-Huperzine A (HupA),3TMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C)[Si](C)(C)C)C1=C(C2)N([Si](C)(C)C)C(=O)C=C1	2667.0	Standard polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2511.9	Semi standard non polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2684.7	Standard non polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2861.0	Standard polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2571.2	Semi standard non polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2617.9	Standard non polar	33892256
(-)-Huperzine A (HupA),1TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2937.1	Standard polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2738.4	Semi standard non polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	3079.7	Standard non polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)[NH]C(=O)C=C1	2935.9	Standard polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2761.0	Semi standard non polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2975.7	Standard non polar	33892256
(-)-Huperzine A (HupA),2TBDMS,isomer #2	CC=C1C2C=C(C)CC1(N[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2858.4	Standard polar	33892256
(-)-Huperzine A (HupA),3TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	3039.0	Semi standard non polar	33892256
(-)-Huperzine A (HupA),3TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	3309.9	Standard non polar	33892256
(-)-Huperzine A (HupA),3TBDMS,isomer #1	CC=C1C2C=C(C)CC1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=C(C2)N([Si](C)(C)C(C)(C)C)C(=O)C=C1	2872.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Huperzine A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ug0-0490000000-c31359bebc16310ab384	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Huperzine A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Huperzine A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Huperzine A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Huperzine A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 10V, Positive-QTOF	splash10-0006-0090000000-e3e64a08a863823cc87b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 20V, Positive-QTOF	splash10-004i-0190000000-42fd35117b41b9725e0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 40V, Positive-QTOF	splash10-0002-0950000000-459982d3bfad21fe36c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 10V, Negative-QTOF	splash10-0006-0090000000-02c4a28e8cf8c263d152	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 20V, Negative-QTOF	splash10-0006-0090000000-6e77b9b16667d062e9a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Huperzine A 40V, Negative-QTOF	splash10-000i-1290000000-61d12cc3903b4282eee1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (-)-Huperzine A (HMDB0242212)

MOL for HMDB0242212 ((-)-Huperzine A)

3D MOL for HMDB0242212 ((-)-Huperzine A)

3D SDF for HMDB0242212 ((-)-Huperzine A)

3D-SDF for HMDB0242212 ((-)-Huperzine A)

PDB for HMDB0242212 ((-)-Huperzine A)

3D PDB for HMDB0242212 ((-)-Huperzine A)

SMILES for HMDB0242212 ((-)-Huperzine A)

INCHI for HMDB0242212 ((-)-Huperzine A)

Structure for HMDB0242212 ((-)-Huperzine A)

3D Structure for HMDB0242212 ((-)-Huperzine A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra