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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:45 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030260

Secondary Accession Numbers

HMDB30260

Metabolite Identification

Common Name

(-)-Quebrachamine

Description

(-)-Quebrachamine, also known as kamassine, belongs to the class of organic compounds known as quebrachamine alkaloids. These are alkaloids with a structure based on the quebrachamine skeleton, a tetracyclic compound that is derived by fission of the 7,21 bond of the aspidospermidine skeleton. Some quebrachamine alkaloids lack the C-16 methoxycarbonyl group. Based on a literature review a significant number of articles have been published on (-)-Quebrachamine.

Structure

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

HMDB0030260
     RDKit          3D
(-)-Quebrachamine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.2469    2.2372   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992    0.9433    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    0.0011    0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.2766    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.5139    0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -2.5170   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.2286   -0.8690 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -1.1130   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    0.2043   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648    0.3122   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    0.1759    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    0.3633    1.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732    0.6263    0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9040    0.8821    0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7533    1.1171   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570    1.0936   -1.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    0.8377   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.5931   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -0.1296    1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    0.7375    1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -0.2548   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    2.7512    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    2.0951   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.9073    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    1.1049    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3709    0.4251    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.2157    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.3322    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716   -3.3622    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552   -2.8001    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.7664   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -3.2703   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3367   -1.1709   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747   -1.9410   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030    1.0751   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.2447   -2.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    0.3285    2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.8896    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7923    1.3152    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372    1.2811   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657    0.8261   -2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.2261    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -0.0760    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.5150    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    1.3417    1.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -0.7206   -1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.6898   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
  7 21  1  0
 20  3  1  0
 21  3  1  0
 18 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
M  END


  Mrv0541 02241214352D          

 21 24  0  0  0  0            999 V2000
   -2.4399    1.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619    0.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2651    0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4477    0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257    0.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243   -0.4314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196   -0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178    1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381    1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    0.9942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491   -0.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    0.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    1.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637   -0.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030260

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC12CCCN(C1)CCC1=C(CC2)NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H26N2/c1-2-19-10-5-12-21(14-19)13-9-16-15-6-3-4-7-17(15)20-18(16)8-11-19/h3-4,6-7,20H,2,5,8-14H2,1H3

> <INCHI_KEY>
FDNDLNFGITWTOZ-UHFFFAOYSA-N

> <FORMULA>
C19H26N2

> <MOLECULAR_WEIGHT>
282.4231

> <EXACT_MASS>
282.209598842

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
34.26295381535503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.1537634043333345

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.12852800770335

> <JCHEM_PKA_STRONGEST_BASIC>
8.899214649266892

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
89.3254

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030260
     RDKit          3D
(-)-Quebrachamine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.2469    2.2372   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992    0.9433    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    0.0011    0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.2766    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.5139    0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -2.5170   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.2286   -0.8690 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -1.1130   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    0.2043   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648    0.3122   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    0.1759    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    0.3633    1.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732    0.6263    0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9040    0.8821    0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7533    1.1171   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570    1.0936   -1.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    0.8377   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.5931   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -0.1296    1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    0.7375    1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -0.2548   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    2.7512    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    2.0951   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.9073    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    1.1049    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3709    0.4251    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.2157    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.3322    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716   -3.3622    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552   -2.8001    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.7664   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -3.2703   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3367   -1.1709   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747   -1.9410   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030    1.0751   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.2447   -2.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    0.3285    2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.8896    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7923    1.3152    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372    1.2811   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657    0.8261   -2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.2261    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -0.0760    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.5150    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    1.3417    1.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -0.7206   -1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.6898   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
  7 21  1  0
 20  3  1  0
 21  3  1  0
 18 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.554   2.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.156   1.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.228   0.014   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.702   0.202   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.101   1.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.026   2.850   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.539  -0.805   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.223  -0.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.568   1.483   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.033   2.901   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.564   3.086   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.492   1.856   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.492   0.315   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.825  -0.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.156   0.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.156   1.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.825   2.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.736  -1.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.914  -1.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.914  -3.086   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.866  -1.101   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    5    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18   19                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   14   21                                                       
CONECT   19   14   20                                                       
CONECT   20   19                                                            
CONECT   21    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0030260
HETATM    1  C1  UNL     1      -3.247   2.237  -0.066  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.499   0.943   0.629  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.315   0.001   0.564  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.567  -1.277   1.252  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.551  -2.514   0.428  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.620  -2.517  -0.749  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.980  -1.229  -0.869  1.00  0.00           N  
HETATM    8  C7  UNL     1       0.053  -1.113  -1.796  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.763   0.204  -1.670  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.665   0.312  -0.491  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.379   0.176   0.810  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.515   0.363   1.527  1.00  0.00           N  
HETATM   13  C11 UNL     1       3.573   0.626   0.729  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.904   0.882   0.972  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.753   1.117  -0.063  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.257   1.094  -1.347  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.930   0.838  -1.575  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.034   0.593  -0.538  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.061  -0.130   1.438  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.062   0.738   1.060  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.042  -0.255  -0.929  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.362   2.751   0.304  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.275   2.095  -1.168  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.123   2.907   0.176  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.712   1.105   1.711  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.371   0.425   0.175  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.603  -1.216   1.709  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.905  -1.332   2.165  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.272  -3.362   1.122  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.555  -2.800   0.040  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.119  -2.766  -1.708  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.819  -3.270  -0.600  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.337  -1.171  -2.852  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.775  -1.941  -1.664  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.103   1.075  -1.797  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.363   0.245  -2.640  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.658   0.329   2.581  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.242   0.890   1.988  1.00  0.00           H  
HETATM   39  H18 UNL     1       6.792   1.315   0.153  1.00  0.00           H  
HETATM   40  H19 UNL     1       5.937   1.281  -2.164  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.566   0.826  -2.613  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.073  -1.226   1.291  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.103  -0.076   2.571  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.743   1.515   0.365  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.487   1.342   1.928  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.972  -0.721  -1.321  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.815   0.690  -1.398  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   20   21
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   21
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   11   18
CONECT   11   12   19
CONECT   12   13   37
CONECT   13   14   14   18
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   19   20   42   43
CONECT   20   44   45
CONECT   21   46   47
END

HMDB0030260
     RDKit          3D
(-)-Quebrachamine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.2469    2.2372   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992    0.9433    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    0.0011    0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.2766    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.5139    0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -2.5170   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.2286   -0.8690 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -1.1130   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    0.2043   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648    0.3122   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    0.1759    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    0.3633    1.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732    0.6263    0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9040    0.8821    0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7533    1.1171   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570    1.0936   -1.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    0.8377   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.5931   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -0.1296    1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    0.7375    1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -0.2548   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    2.7512    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    2.0951   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.9073    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    1.1049    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3709    0.4251    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.2157    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.3322    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716   -3.3622    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552   -2.8001    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.7664   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -3.2703   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3367   -1.1709   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747   -1.9410   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030    1.0751   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.2447   -2.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    0.3285    2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.8896    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7923    1.3152    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372    1.2811   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657    0.8261   -2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.2261    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -0.0760    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.5150    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    1.3417    1.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -0.7206   -1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.6898   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
  7 21  1  0
 20  3  1  0
 21  3  1  0
 18 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Kamassine	HMDB
Quebrachamin	HMDB
Quebrachamine	HMDB

Chemical Formula

C₁₉H₂₆N₂

Average Molecular Weight

282.4231

Monoisotopic Molecular Weight

282.209598842

IUPAC Name

15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene

Traditional Name

15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene

CAS Registry Number

4850-21-9

SMILES

CCC12CCCN(C1)CCC1=C(CC2)NC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H26N2/c1-2-19-10-5-12-21(14-19)13-9-16-15-6-3-4-7-17(15)20-18(16)8-11-19/h3-4,6-7,20H,2,5,8-14H2,1H3

InChI Key

FDNDLNFGITWTOZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quebrachamine alkaloids. These are alkaloids with a structure based on the quebrachamine skeleton, a tetracyclic compound that is derived by fission of the 7,21 bond of the aspidospermidine skeleton. Some quebrachamine alkaloids lack the C-16 methoxycarbonyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Quebrachamine alkaloids

Sub Class

Not Available

Direct Parent

Quebrachamine alkaloids

Alternative Parents

Substituents

Quebrachamine skeleton
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030260)
Cell membrane (HMDB: HMDB0030260)

Source

Endogenous

Endogenous (HMDB: HMDB0030260)

Exogenous

Food

Food (HMDB: HMDB0030260)

Exogenous (HMDB: HMDB0030260)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 - 149 °C	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
Water Solubility	0.0071 g/L	ALOGPS
logP	4.5	ALOGPS
logP	4.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.13	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.33 m³·mol⁻¹	ChemAxon
Polarizability	34.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.27	31661259
DarkChem	[M-H]-	166.348	31661259
DeepCCS	[M-2H]-	198.844	30932474
DeepCCS	[M+Na]+	174.409	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	181.4	32859911
AllCCS	[M+HCOO]-	181.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.86 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1734 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1671.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	493.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	453.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	385.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	905.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	453.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1498.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	338.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	275.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Quebrachamine	CCC12CCCN(C1)CCC1=C(CC2)NC2=CC=CC=C12	3651.6	Standard polar	33892256
(-)-Quebrachamine	CCC12CCCN(C1)CCC1=C(CC2)NC2=CC=CC=C12	2497.4	Standard non polar	33892256
(-)-Quebrachamine	CCC12CCCN(C1)CCC1=C(CC2)NC2=CC=CC=C12	2608.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Quebrachamine,1TMS,isomer #1	CCC12CCCN(CCC3=C(CC1)N([Si](C)(C)C)C1=CC=CC=C31)C2	2619.9	Semi standard non polar	33892256
(-)-Quebrachamine,1TMS,isomer #1	CCC12CCCN(CCC3=C(CC1)N([Si](C)(C)C)C1=CC=CC=C31)C2	2547.3	Standard non polar	33892256
(-)-Quebrachamine,1TBDMS,isomer #1	CCC12CCCN(CCC3=C(CC1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31)C2	2808.1	Semi standard non polar	33892256
(-)-Quebrachamine,1TBDMS,isomer #1	CCC12CCCN(CCC3=C(CC1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31)C2	2805.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Quebrachamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufr-1090000000-9c18d89209be5a025da8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Quebrachamine 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 - (-)-Quebrachamine 10V, Positive-QTOF	splash10-001i-0090000000-a64f4ae045d84a5cbee5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 20V, Positive-QTOF	splash10-001i-0090000000-a3889ddf9c2a611d1cd4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 40V, Positive-QTOF	splash10-01pn-7900000000-f7242204d1b7be9a9a8c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 10V, Negative-QTOF	splash10-001i-0090000000-203484040fd417776357	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 20V, Negative-QTOF	splash10-001i-0090000000-9254d5f248ef262ade22	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 40V, Negative-QTOF	splash10-0i00-1790000000-245414f0b17a067bbafe	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 10V, Negative-QTOF	splash10-001i-0090000000-4af417b6c8cdf87c31f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 20V, Negative-QTOF	splash10-001i-0090000000-4af417b6c8cdf87c31f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 40V, Negative-QTOF	splash10-0ue9-1090000000-fd13a75f570141a093bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 10V, Positive-QTOF	splash10-001i-0090000000-48c8d6d60cf70e82e98f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 20V, Positive-QTOF	splash10-001i-0090000000-64e9ad15f1434b79b6dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Quebrachamine 40V, Positive-QTOF	splash10-114l-0090000000-907d3d669def01237b1d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

624708

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (-)-Quebrachamine (HMDB0030260)

MOL for HMDB0030260 ((-)-Quebrachamine)

3D MOL for HMDB0030260 ((-)-Quebrachamine)

3D SDF for HMDB0030260 ((-)-Quebrachamine)

3D-SDF for HMDB0030260 ((-)-Quebrachamine)

PDB for HMDB0030260 ((-)-Quebrachamine)

3D PDB for HMDB0030260 ((-)-Quebrachamine)

SMILES for HMDB0030260 ((-)-Quebrachamine)

INCHI for HMDB0030260 ((-)-Quebrachamine)

Structure for HMDB0030260 ((-)-Quebrachamine)

3D Structure for HMDB0030260 ((-)-Quebrachamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra