Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:09:59 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033432

Secondary Accession Numbers

HMDB33432

Metabolite Identification

Common Name

(R)-Rhazinilam

Description

(R)-Rhazinilam belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings (R)-Rhazinilam is an extremely weak basic (essentially neutral) compound (based on its pKa). Alkaloidal artifact from Aspidosperma quebracho-blanco (quebracho).

Structure

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

HMDB0033432
     RDKit          3D
(R)-Rhazinilam
 44 47  0  0  0  0  0  0  0  0999 V2000
   -1.0144   -0.5374    2.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309   -0.6106    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.3620   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -0.4864   -1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    0.6721   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6989    1.9822   -1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    2.0060   -0.7809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009    3.0742   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902    2.6687   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.2753   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    1.0003   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.5351    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    1.0766    1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035    0.6018    2.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -0.4982    2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510   -1.0525    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.5810    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -1.3696   -1.0676 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -2.0920   -1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -2.6979   -2.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739   -2.4163   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652   -1.1744   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6864   -0.5173    3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -1.3811    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    0.4667    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7115    0.1898    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -1.5898    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871   -1.3992   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -0.6107   -2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0908    0.5881   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0529    0.5394   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212    2.7008   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.3919   -2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    4.0913   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    3.3643   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068    1.9770    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382    1.0346    3.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.9254    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -1.9206    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -2.3332   -3.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355   -3.3279   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942   -2.5305   -2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4644   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -1.3578    0.4717 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 11  3  1  0
 17 12  1  0
 22  3  1  0
 11  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END


  Mrv0541 05061307072D          

 22 25  0  0  0  0            999 V2000
    0.7244   -0.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6581    1.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221    0.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537   -0.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2420    2.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3048    0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396   -0.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529    1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4570    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0090    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435    1.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3976    0.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783   -0.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    1.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234    0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275   -0.3505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    1.9025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 13  9  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 18 15  2  0  0  0  0
 19  2  1  0  0  0  0
 19 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  2  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 21 18  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033432

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC12CCCN3C=CC(=C13)C1=CC=CC=C1\N=C(O)/CC2

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)

> <INCHI_KEY>
VLQAFTDOIRUYSZ-UHFFFAOYSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.3908

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.35090521197578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8E)-12-ethyl-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-9-ol

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.562101514666667

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.631157054824041

> <JCHEM_PKA_STRONGEST_BASIC>
0.929401149570713

> <JCHEM_POLAR_SURFACE_AREA>
37.519999999999996

> <JCHEM_REFRACTIVITY>
90.7053

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8E)-12-ethyl-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-9-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033432
     RDKit          3D
(R)-Rhazinilam
 44 47  0  0  0  0  0  0  0  0999 V2000
   -1.0144   -0.5374    2.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309   -0.6106    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.3620   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -0.4864   -1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    0.6721   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6989    1.9822   -1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    2.0060   -0.7809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009    3.0742   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902    2.6687   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.2753   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    1.0003   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.5351    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    1.0766    1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035    0.6018    2.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -0.4982    2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510   -1.0525    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.5810    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -1.3696   -1.0676 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -2.0920   -1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -2.6979   -2.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739   -2.4163   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652   -1.1744   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6864   -0.5173    3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -1.3811    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    0.4667    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7115    0.1898    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -1.5898    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871   -1.3992   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -0.6107   -2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0908    0.5881   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0529    0.5394   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212    2.7008   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.3919   -2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    4.0913   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    3.3643   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068    1.9770    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382    1.0346    3.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.9254    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -1.9206    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -2.3332   -3.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355   -3.3279   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942   -2.5305   -2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4644   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -1.3578    0.4717 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 11  3  1  0
 17 12  1  0
 22  3  1  0
 11  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.352  -0.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.885  -0.256   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.836   3.468   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.562   2.109   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.528   1.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.297   3.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748   0.802   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.140  -1.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.052   4.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.436   0.735   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.994  -0.525   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.152   3.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.586   4.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.483   2.211   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.055   2.785   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.209   0.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.679  -1.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.591   2.307   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.777   1.000   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       7.891  -0.654   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       3.683   3.551   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       7.158  -3.068   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   19                                                       
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5   10   12                                                       
CONECT    6    3   14                                                       
CONECT    7    4   16                                                       
CONECT    8   11   17                                                       
CONECT    9   13   15                                                       
CONECT   10    5   19                                                       
CONECT   11    8   19                                                       
CONECT   12    5   21                                                       
CONECT   13    9   21                                                       
CONECT   14    6   15   16                                                  
CONECT   15    9   14   18                                                  
CONECT   16    7   14   20                                                  
CONECT   17    8   20   22                                                  
CONECT   18   15   19   21                                                  
CONECT   19    2   10   11   18                                             
CONECT   20   16   17                                                       
CONECT   21   12   13   18                                                  
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033432
HETATM    1  C1  UNL     1      -1.014  -0.537   2.227  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.931  -0.611   1.061  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.302  -0.362  -0.286  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.426  -0.486  -1.299  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.382   0.672  -1.154  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.699   1.982  -1.188  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.322   2.006  -0.781  1.00  0.00           N  
HETATM    8  C7  UNL     1      -0.501   3.074  -0.757  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.690   2.669  -0.299  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.654   1.275  -0.008  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.636   1.000  -0.351  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.792   0.535   0.549  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.270   1.077   1.780  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.304   0.602   2.517  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.969  -0.498   2.061  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.551  -1.053   0.887  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.476  -0.581   0.095  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.295  -1.370  -1.068  1.00  0.00           N  
HETATM   19  C17 UNL     1       1.509  -2.092  -1.702  1.00  0.00           C  
HETATM   20  O1  UNL     1       1.812  -2.698  -2.901  1.00  0.00           O  
HETATM   21  C18 UNL     1       0.074  -2.416  -1.242  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.165  -1.174  -0.530  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.686  -0.517   3.142  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.348  -1.381   2.395  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.513   0.467   2.285  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.712   0.190   1.226  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.457  -1.590   1.038  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.987  -1.399  -1.011  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.080  -0.611  -2.324  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.091   0.588  -2.022  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.053   0.539  -0.261  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.321   2.701  -0.591  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.815   2.392  -2.244  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.775   4.091  -1.064  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.529   3.364  -0.178  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.807   1.977   2.223  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.638   1.035   3.447  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.809  -0.925   2.621  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.160  -1.921   0.600  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.586  -2.333  -3.453  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.135  -3.328  -0.641  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.594  -2.531  -2.090  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.488  -0.464  -1.184  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.262  -1.358   0.472  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   11   22
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   11
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18
CONECT   18   19   19
CONECT   19   20   21
CONECT   20   40
CONECT   21   22   41   42
CONECT   22   43   44
END

HMDB0033432
     RDKit          3D
(R)-Rhazinilam
 44 47  0  0  0  0  0  0  0  0999 V2000
   -1.0144   -0.5374    2.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309   -0.6106    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.3620   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -0.4864   -1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    0.6721   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6989    1.9822   -1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    2.0060   -0.7809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009    3.0742   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902    2.6687   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.2753   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    1.0003   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.5351    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    1.0766    1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035    0.6018    2.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -0.4982    2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510   -1.0525    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.5810    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -1.3696   -1.0676 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -2.0920   -1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -2.6979   -2.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739   -2.4163   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652   -1.1744   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6864   -0.5173    3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -1.3811    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    0.4667    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7115    0.1898    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -1.5898    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871   -1.3992   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -0.6107   -2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0908    0.5881   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0529    0.5394   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212    2.7008   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.3919   -2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    4.0913   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    3.3643   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068    1.9770    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382    1.0346    3.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.9254    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -1.9206    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -2.3332   -3.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355   -3.3279   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942   -2.5305   -2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4644   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -1.3578    0.4717 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 11  3  1  0
 17 12  1  0
 22  3  1  0
 11  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Rhazinilam	HMDB
Rhazinilam	HMDB
Rhazinilam, (8ar,14ar)-(+-)-isomer	HMDB

Chemical Formula

C₁₉H₂₂N₂O

Average Molecular Weight

294.3908

Monoisotopic Molecular Weight

294.173213336

IUPAC Name

(8E)-12-ethyl-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-9-ol

Traditional Name

(8E)-12-ethyl-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-9-ol

CAS Registry Number

36193-36-9

SMILES

CCC12CCCN3C=CC(=C13)C1=CC=CC=C1\N=C(O)/CC2

InChI Identifier

InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)

InChI Key

VLQAFTDOIRUYSZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Not Available

Sub Class

Not Available

Direct Parent

Benzenoids

Alternative Parents

Substituents

Benzenoid
Pyrrole
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033432)

Membrane (HMDB: HMDB0033432)
Cell membrane (HMDB: HMDB0033432)

Source

Exogenous

Food

Food (HMDB: HMDB0033432)

Not Available

Nutrient (HMDB: HMDB0033432)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	214 - 216 °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	0.027 g/L	ALOGPS
logP	4.05	ALOGPS
logP	4.56	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	0.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.71 m³·mol⁻¹	ChemAxon
Polarizability	33.35 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]+	168.675	31661259
DarkChem	[M-H]-	169.964	31661259
DeepCCS	[M-2H]-	200.471	30932474
DeepCCS	[M+Na]+	175.954	30932474
AllCCS	[M+H]+	171.5	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	179.8	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	179.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Rhazinilam	CCC12CCCN3C=CC(=C13)C1=CC=CC=C1\N=C(O)/CC2	3882.8	Standard polar	33892256
(R)-Rhazinilam	CCC12CCCN3C=CC(=C13)C1=CC=CC=C1\N=C(O)/CC2	2662.9	Standard non polar	33892256
(R)-Rhazinilam	CCC12CCCN3C=CC(=C13)C1=CC=CC=C1\N=C(O)/CC2	2644.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Rhazinilam,1TMS,isomer #1	CCC12CCCN3C=CC(=C31)C1=CC=CC=C1/N=C(/O[Si](C)(C)C)CC2	2733.2	Semi standard non polar	33892256
(R)-Rhazinilam,1TBDMS,isomer #1	CCC12CCCN3C=CC(=C31)C1=CC=CC=C1/N=C(/O[Si](C)(C)C(C)(C)C)CC2	2917.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Rhazinilam GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-0090000000-8436e2e707b1cd7f318c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Rhazinilam GC-MS (1 TMS) - 70eV, Positive	splash10-0fe0-5009000000-ebefced934037770ab98	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Rhazinilam 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 - (R)-Rhazinilam 10V, Positive-QTOF	splash10-0002-0090000000-6f352d58c241f6f98055	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 20V, Positive-QTOF	splash10-0002-0090000000-82fb0542e49ad84900df	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 40V, Positive-QTOF	splash10-00b9-9530000000-e7252d322b2678f51666	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 10V, Negative-QTOF	splash10-0006-0090000000-1be6e6323949bb41d545	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 20V, Negative-QTOF	splash10-0006-0090000000-15bd2de0d5259199fe3d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 40V, Negative-QTOF	splash10-0006-9020000000-5492a9217abd0309f502	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 10V, Positive-QTOF	splash10-0002-0090000000-66031f2ab6d829714f21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 20V, Positive-QTOF	splash10-0002-0090000000-0a5febd5d7e43bf1054b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 40V, Positive-QTOF	splash10-014i-0090000000-366dfe4d104f43c0bcf1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 10V, Negative-QTOF	splash10-0006-0090000000-b8900ba29f28c2c35417	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 20V, Negative-QTOF	splash10-0006-0090000000-b8900ba29f28c2c35417	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Rhazinilam 40V, Negative-QTOF	splash10-01ot-0090000000-3dc1d8fe2789c44187e2	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

FDB011470

KNApSAcK ID

C00024595

Chemspider ID

140859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160263

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 (R)-Rhazinilam (HMDB0033432)

MOL for HMDB0033432 ((R)-Rhazinilam)

3D MOL for HMDB0033432 ((R)-Rhazinilam)

3D SDF for HMDB0033432 ((R)-Rhazinilam)

3D-SDF for HMDB0033432 ((R)-Rhazinilam)

PDB for HMDB0033432 ((R)-Rhazinilam)

3D PDB for HMDB0033432 ((R)-Rhazinilam)

SMILES for HMDB0033432 ((R)-Rhazinilam)

INCHI for HMDB0033432 ((R)-Rhazinilam)

Structure for HMDB0033432 ((R)-Rhazinilam)

3D Structure for HMDB0033432 ((R)-Rhazinilam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra