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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:32:48 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0253233

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Huperzine B

Description

Huperzine B, also known as fordimine, belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring. Based on a literature review very few articles have been published on Huperzine B. This compound has been identified in human blood as reported by (PMID: 31557052 ). Huperzine b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Huperzine B 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

HMDB0253233
     RDKit          3D
huperzine b
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7803    3.6229    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764    2.2237   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    1.8031   -1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6017   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539   -0.5405   -2.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -0.9496   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191   -1.5639   -1.1543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.9621   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695   -2.5293   -0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403   -1.7323    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.1007    1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.6987    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.0282    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509    1.3711    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -0.7932    1.6462 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -0.8502    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389   -1.1948    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.0706   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.1834   -0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    4.2841   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    3.5888    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    3.9990    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    2.3538   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727    0.8367   -2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -0.2841   -2.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -1.3948   -2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -1.7289   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851   -2.0689    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.9395    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    1.2911    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    1.8316    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.3890    2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    0.0900    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439   -1.6554    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309   -0.4344   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.1734    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -1.0697   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -1.9323   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759    1.0036   -0.4625 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 19  4  1  0
 12  6  2  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

3348
  Mrv0541 02231216522D          

 19 22  0  0  0  0            999 V2000
   -1.9880   -0.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451   -0.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -0.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365    0.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2428    0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899    1.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030    1.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951    1.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6852    2.7588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356    1.1881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    0.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331   -0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -1.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466   -1.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -1.2153    0.0000 C   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  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
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253233

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)

> <INCHI_KEY>
YYWGABLTRMRUIT-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.3428

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.43289646380274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,16-trien-5-one

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.6735153546668239

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.217638919396169

> <JCHEM_PKA_STRONGEST_BASIC>
9.766980026522516

> <JCHEM_POLAR_SURFACE_AREA>
41.13

> <JCHEM_REFRACTIVITY>
78.065

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,16-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253233
     RDKit          3D
huperzine b
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7803    3.6229    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764    2.2237   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    1.8031   -1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6017   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539   -0.5405   -2.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -0.9496   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191   -1.5639   -1.1543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.9621   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695   -2.5293   -0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403   -1.7323    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.1007    1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.6987    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.0282    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509    1.3711    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -0.7932    1.6462 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -0.8502    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389   -1.1948    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.0706   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.1834   -0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    4.2841   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    3.5888    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    3.9990    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    2.3538   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727    0.8367   -2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -0.2841   -2.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -1.3948   -2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -1.7289   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851   -2.0689    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.9395    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    1.2911    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    1.8316    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.3890    2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    0.0900    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439   -1.6554    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309   -0.4344   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.1734    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -1.0697   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -1.9323   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759    1.0036   -0.4625 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 19  4  1  0
 12  6  2  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3348                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.711  -0.854   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.138  -1.135   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.856  -2.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.432  -2.989   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.150  -1.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.001   0.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.453   0.753   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.288   2.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.566   3.473   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.924   3.548   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.279   5.150   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.746   2.218   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.790  -0.729   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.760  -0.230   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.090   0.058   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.422  -0.658   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.458  -2.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.140  -3.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.790  -2.269   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
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   14   15   19                                             
CONECT   14   13    2                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4   13                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0253233
HETATM    1  C1  UNL     1      -0.780   3.623   0.290  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.376   2.224  -0.015  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.414   1.803  -1.269  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.330   0.602  -1.735  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.554  -0.540  -2.108  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.341  -0.950  -0.925  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.519  -1.564  -1.154  1.00  0.00           N  
HETATM    8  C7  UNL     1      -3.282  -1.962  -0.127  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.370  -2.529  -0.366  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.840  -1.732   1.153  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.629  -1.101   1.414  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.859  -0.699   0.323  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.423  -0.028   0.644  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.051   1.371   1.125  1.00  0.00           C  
HETATM   15  N2  UNL     1       1.080  -0.793   1.646  1.00  0.00           N  
HETATM   16  C13 UNL     1       2.498  -0.850   1.557  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.039  -1.195   0.214  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.001  -1.071  -0.885  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.242   0.183  -0.610  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.555   4.284  -0.559  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.893   3.589   0.452  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.296   3.999   1.210  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.009   2.354  -1.984  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.973   0.837  -2.621  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.251  -0.284  -2.932  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.095  -1.395  -2.376  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.836  -1.729  -2.122  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.485  -2.069   1.959  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.319  -0.939   2.424  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.794   1.291   1.828  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.895   1.832   1.696  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.830  -0.389   2.581  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.943   0.090   1.981  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.844  -1.655   2.269  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.831  -0.434  -0.033  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.559  -2.173   0.179  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.507  -1.070  -1.870  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.286  -1.932  -0.791  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.976   1.004  -0.462  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   14
CONECT    3    4   23
CONECT    4    5   19   24
CONECT    5    6   25   26
CONECT    6    7   12   12
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13
CONECT   13   14   15   19
CONECT   14   30   31
CONECT   15   16   32
CONECT   16   17   33   34
CONECT   17   18   35   36
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0253233
     RDKit          3D
huperzine b
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7803    3.6229    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764    2.2237   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    1.8031   -1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6017   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539   -0.5405   -2.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -0.9496   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191   -1.5639   -1.1543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.9621   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695   -2.5293   -0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403   -1.7323    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.1007    1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.6987    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.0282    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509    1.3711    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -0.7932    1.6462 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -0.8502    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389   -1.1948    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.0706   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.1834   -0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    4.2841   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    3.5888    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    3.9990    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    2.3538   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727    0.8367   -2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -0.2841   -2.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -1.3948   -2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -1.7289   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851   -2.0689    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.9395    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    1.2911    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    1.8316    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.3890    2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    0.0900    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439   -1.6554    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309   -0.4344   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.1734    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -1.0697   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -1.9323   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759    1.0036   -0.4625 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 19  4  1  0
 12  6  2  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fordimine	HMDB
Huperzine b	MeSH

Chemical Formula

C₁₆H₂₀N₂O

Average Molecular Weight

256.3428

Monoisotopic Molecular Weight

256.157563272

IUPAC Name

16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,16-trien-5-one

Traditional Name

16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,16-trien-5-one

CAS Registry Number

Not Available

SMILES

CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23

InChI Identifier

InChI=1S/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)

InChI Key

YYWGABLTRMRUIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

1,7-phenanthroline
Quinolone
Aralkylamine
Pyridinone
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Secondary aliphatic amine
Azacycle
Secondary amine
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
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	1.31	ALOGPS
logP	0.67	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	28.43 Å³	ChemAxon
Number of Rings	4	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-2H]-	195.553	30932474
DeepCCS	[M+Na]+	171.019	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.8	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	165.0	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	167.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
huperzine b	CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23	3363.4	Standard polar	33892256
huperzine b	CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23	2418.5	Standard non polar	33892256
huperzine b	CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23	2508.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
huperzine b,1TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)NCCCC23	2553.4	Semi standard non polar	33892256
huperzine b,1TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)NCCCC23	2532.1	Standard non polar	33892256
huperzine b,1TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)NCCCC23	2889.9	Standard polar	33892256
huperzine b,1TMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C	2464.4	Semi standard non polar	33892256
huperzine b,1TMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C	2652.8	Standard non polar	33892256
huperzine b,1TMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C	2956.7	Standard polar	33892256
huperzine b,2TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C	2503.7	Semi standard non polar	33892256
huperzine b,2TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C	2688.6	Standard non polar	33892256
huperzine b,2TMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C	2914.0	Standard polar	33892256
huperzine b,1TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)NCCCC23	2752.5	Semi standard non polar	33892256
huperzine b,1TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)NCCCC23	2791.4	Standard non polar	33892256
huperzine b,1TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)NCCCC23	3040.8	Standard polar	33892256
huperzine b,1TBDMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	2692.3	Semi standard non polar	33892256
huperzine b,1TBDMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	2869.5	Standard non polar	33892256
huperzine b,1TBDMS,isomer #2	CC1=CC2CC3=C(C=CC(=O)[NH]3)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	3105.2	Standard polar	33892256
huperzine b,2TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	2915.7	Semi standard non polar	33892256
huperzine b,2TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	3156.4	Standard non polar	33892256
huperzine b,2TBDMS,isomer #1	CC1=CC2CC3=C(C=CC(=O)N3[Si](C)(C)C(C)(C)C)C3(C1)C2CCCN3[Si](C)(C)C(C)(C)C	3104.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Huperzine B GC-MS (Non-derivatized) - 70eV, Positive	splash10-01tc-0090000000-65bfcc4de84b93f70b46	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Huperzine B 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 B 10V, Positive-QTOF	splash10-0a4i-0090000000-67e1ca079b55cc10341e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huperzine B 20V, Positive-QTOF	splash10-0a4i-0090000000-466f5dfd717c02328f8d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huperzine B 40V, Positive-QTOF	splash10-03dj-0890000000-bd08b37c57d81cc2d8ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huperzine B 10V, Negative-QTOF	splash10-0a4i-0090000000-d58e919b02e6e2481eb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huperzine B 20V, Negative-QTOF	splash10-0a4i-0090000000-d58e919b02e6e2481eb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huperzine B 40V, Negative-QTOF	splash10-0k9l-1390000000-a2376d24537a07c37b62	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

3505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3631

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 B (HMDB0253233)

MOL for HMDB0253233 (Huperzine B)

3D MOL for HMDB0253233 (Huperzine B)

3D SDF for HMDB0253233 (Huperzine B)

3D-SDF for HMDB0253233 (Huperzine B)

PDB for HMDB0253233 (Huperzine B)

3D PDB for HMDB0253233 (Huperzine B)

SMILES for HMDB0253233 (Huperzine B)

INCHI for HMDB0253233 (Huperzine B)

Structure for HMDB0253233 (Huperzine B)

3D Structure for HMDB0253233 (Huperzine B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra