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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:59 UTC

Update Date

2022-03-07 02:53:25 UTC

HMDB ID

HMDB0032650

Secondary Accession Numbers

HMDB32650

Metabolite Identification

Common Name

Litcubinine

Description

Litcubinine belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Based on a literature review a significant number of articles have been published on Litcubinine.

Structure

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

HMDB0032650
     RDKit          3D
Litcubinine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.4197    2.3050   -1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    1.8639    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068    0.9689    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315    0.4915   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -0.4242   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.8634    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.3693    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    0.5259    1.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3083    1.0107    2.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262   -1.8366    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802   -1.3514    1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.1488    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246    1.0062    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9691    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877    3.1675    1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    1.7449   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808    2.7319   -1.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090    0.5484   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.4339   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.7201   -0.3945 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1843   -2.6836   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -1.9162   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -0.8774   -1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    2.9935   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5102    2.7875   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6376    1.4141   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033    0.8151   -1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762   -0.7235    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216    0.6833    3.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1177   -2.8582    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.1109    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305   -2.1315    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1850    2.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293    3.3329    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    2.6462   -2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    0.4121   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0933   -2.2265    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -2.9579   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -3.6234    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -2.0694   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.9051   -1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -1.3555   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430   -0.0167   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 20 10  1  0
 23  5  1  0
 19 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  CHG  1  20   1
M  END

  Mrv0541 05061306372D          

 23 26  0  0  0  0            999 V2000
    4.7554   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776   -2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -0.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486   -0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142   -2.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -2.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7486   -0.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0066   -2.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9249   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426   -2.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5539   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7303   -1.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -1.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8302   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012   -1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.9832    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2820   -2.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604   -0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2829   -2.9581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -1.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17  8  1  0  0  0  0
 18  7  1  0  0  0  0
 18 17  2  0  0  0  0
 19  1  1  0  0  0  0
 19  4  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
M  CHG  1  19   1
M  END
> <DATABASE_ID>
HMDB0032650

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO4/c1-19-4-3-10-7-18(23-2)17(22)8-12(10)14(19)5-11-6-15(20)16(21)9-13(11)19/h6-9,14H,3-5H2,1-2H3,(H2-,20,21,22)/p+1

> <INCHI_KEY>
HVZWFRMKXRRMBK-UHFFFAOYSA-O

> <FORMULA>
C18H20NO4

> <MOLECULAR_WEIGHT>
314.3557

> <EXACT_MASS>
314.139233133

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.084941255120256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,9,10-trihydroxy-3-methoxy-7-methyl-5H,6H,7H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
-1.1713999914717461

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.350854807123997

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.172383952681601

> <JCHEM_PKA_STRONGEST_BASIC>
-4.89286645816497

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
98.9872

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,9,10-trihydroxy-3-methoxy-7-methyl-5H,6H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032650
     RDKit          3D
Litcubinine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.4197    2.3050   -1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    1.8639    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068    0.9689    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315    0.4915   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -0.4242   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.8634    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.3693    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    0.5259    1.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3083    1.0107    2.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262   -1.8366    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802   -1.3514    1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.1488    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246    1.0062    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9691    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877    3.1675    1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    1.7449   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808    2.7319   -1.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090    0.5484   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.4339   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.7201   -0.3945 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1843   -2.6836   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -1.9162   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -0.8774   -1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    2.9935   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5102    2.7875   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6376    1.4141   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033    0.8151   -1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762   -0.7235    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216    0.6833    3.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1177   -2.8582    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.1109    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305   -2.1315    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1850    2.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293    3.3329    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    2.6462   -2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    0.4121   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0933   -2.2265    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -2.9579   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -3.6234    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -2.0694   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.9051   -1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -1.3555   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430   -0.0167   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 20 10  1  0
 23  5  1  0
 19 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  CHG  1  20   1
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       8.877  -0.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.692  -4.058   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.082  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.544  -0.460   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.733  -4.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.924  -4.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.464  -1.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.079  -4.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.070  -1.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.926  -1.659   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.293  -3.779   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.234  -3.035   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.366  -2.241   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.697  -3.123   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.628  -3.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.702  -2.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.616  -4.234   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.309  -2.859   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       9.852  -1.835   0.000  0.00  0.00           N+1
HETATM   20  O   UNK     0       4.260  -4.358   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.406  -1.282   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      15.461  -5.522   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.846  -2.771   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   23                                                            
CONECT    3    4   10                                                       
CONECT    4    3   19                                                       
CONECT    5   11   14                                                       
CONECT    6   11   15                                                       
CONECT    7   10   18                                                       
CONECT    8   12   17                                                       
CONECT    9   13   16                                                       
CONECT   10    3    7   12                                                  
CONECT   11    5    6   13                                                  
CONECT   12    8   10   14                                                  
CONECT   13    9   11   19                                                  
CONECT   14    5   12   19                                                  
CONECT   15    6   16   20                                                  
CONECT   16    9   15   21                                                  
CONECT   17    8   18   22                                                  
CONECT   18    7   17   23                                                  
CONECT   19    1    4   13   14                                             
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0032650
HETATM    1  C1  UNL     1       4.420   2.305  -1.095  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.042   1.864   0.196  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.007   0.969   0.308  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.331   0.491  -0.780  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.270  -0.424  -0.689  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.889  -0.863   0.553  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.585  -0.369   1.654  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.621   0.526   1.547  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.308   1.011   2.662  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.226  -1.837   0.764  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.180  -1.351   1.841  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.733  -0.149   1.123  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.225   1.006   1.646  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.676   1.969   0.756  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.188   3.168   1.254  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.620   1.745  -0.588  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.081   2.732  -1.445  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.109   0.548  -1.084  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.650  -0.434  -0.224  1.00  0.00           C  
HETATM   20  N1  UNL     1      -1.092  -1.720  -0.394  1.00  0.00           N1+
HETATM   21  C16 UNL     1      -2.184  -2.684  -0.336  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.400  -1.916  -1.628  1.00  0.00           C  
HETATM   23  C18 UNL     1       0.604  -0.877  -1.958  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.278   2.994  -1.038  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.510   2.787  -1.537  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.638   1.414  -1.753  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.603   0.815  -1.776  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.276  -0.723   2.629  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.022   0.683   3.561  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.118  -2.858   0.923  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.716  -1.111   2.785  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.930  -2.132   1.982  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.270   1.185   2.700  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.229   3.333   2.246  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.075   2.646  -2.459  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.084   0.412  -2.155  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.093  -2.227   0.113  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.481  -2.958  -1.389  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.897  -3.623   0.147  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.164  -2.069  -2.423  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.128  -2.905  -1.546  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.409  -1.355  -2.563  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.243  -0.017  -2.530  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   23
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   29
CONECT   10   11   20   30
CONECT   11   12   31   32
CONECT   12   13   13   19
CONECT   13   14   33
CONECT   14   15   16   16
CONECT   15   34
CONECT   16   17   18
CONECT   17   35
CONECT   18   19   19   36
CONECT   19   20
CONECT   20   21   22
CONECT   21   37   38   39
CONECT   22   23   40   41
CONECT   23   42   43
END

HMDB0032650
     RDKit          3D
Litcubinine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.4197    2.3050   -1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    1.8639    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068    0.9689    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315    0.4915   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -0.4242   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.8634    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.3693    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    0.5259    1.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3083    1.0107    2.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262   -1.8366    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802   -1.3514    1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.1488    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246    1.0062    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9691    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877    3.1675    1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    1.7449   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808    2.7319   -1.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090    0.5484   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.4339   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.7201   -0.3945 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1843   -2.6836   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -1.9162   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -0.8774   -1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    2.9935   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5102    2.7875   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6376    1.4141   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033    0.8151   -1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762   -0.7235    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216    0.6833    3.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1177   -2.8582    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.1109    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305   -2.1315    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1850    2.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293    3.3329    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    2.6462   -2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    0.4121   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0933   -2.2265    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -2.9579   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -3.6234    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -2.0694   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.9051   -1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -1.3555   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430   -0.0167   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 20 10  1  0
 23  5  1  0
 19 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  CHG  1  20   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Litcubinine	HMDB

Chemical Formula

C₁₈H₂₀NO₄

Average Molecular Weight

314.3557

Monoisotopic Molecular Weight

314.139233133

IUPAC Name

2,9,10-trihydroxy-3-methoxy-7-methyl-5H,6H,7H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

Traditional Name

2,9,10-trihydroxy-3-methoxy-7-methyl-5H,6H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

CAS Registry Number

172924-24-2

SMILES

COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1

InChI Identifier

InChI=1S/C18H19NO4/c1-19-4-3-10-7-18(23-2)17(22)8-12(10)14(19)5-11-6-15(20)16(21)9-13(11)19/h6-9,14H,3-5H2,1-2H3,(H2-,20,21,22)/p+1

InChI Key

HVZWFRMKXRRMBK-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Indole or derivatives
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Benzenoid
Quaternary ammonium salt
Ether
Polyol
Azacycle
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic salt
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032650)
Cytoplasm (HMDB: HMDB0032650)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032650)

Source

Endogenous

Endogenous (HMDB: HMDB0032650)

Plant

Plant (HMDB: HMDB0032650)

Exogenous

Food

Food (HMDB: HMDB0032650)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0032650)

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
Water Solubility	0.0058 g/L	ALOGPS
logP	1.42	ALOGPS
logP	-1.2	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.99 m³·mol⁻¹	ChemAxon
Polarizability	34.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	171.456	31661259
DarkChem	[M-H]-	171.021	31661259
DeepCCS	[M+H]+	179.409	30932474
DeepCCS	[M-H]-	176.903	30932474
DeepCCS	[M-2H]-	211.342	30932474
DeepCCS	[M+Na]+	186.852	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.7	32859911
AllCCS	[M-H]-	183.9	32859911
AllCCS	[M+Na-2H]-	184.2	32859911
AllCCS	[M+HCOO]-	184.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Litcubinine	COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1	4553.3	Standard polar	33892256
Litcubinine	COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1	2879.8	Standard non polar	33892256
Litcubinine	COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1	3182.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Litcubinine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC(O)=C(O)C=C3[N+]1(C)CC2	3002.2	Semi standard non polar	33892256
Litcubinine,1TMS,isomer #2	COC1=CC2=C(C=C1O)C1CC3=CC(O[Si](C)(C)C)=C(O)C=C3[N+]1(C)CC2	3034.1	Semi standard non polar	33892256
Litcubinine,1TMS,isomer #3	COC1=CC2=C(C=C1O)C1CC3=CC(O)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	3020.6	Semi standard non polar	33892256
Litcubinine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC(O[Si](C)(C)C)=C(O)C=C3[N+]1(C)CC2	3008.7	Semi standard non polar	33892256
Litcubinine,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC(O)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	2989.4	Semi standard non polar	33892256
Litcubinine,2TMS,isomer #3	COC1=CC2=C(C=C1O)C1CC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	3017.6	Semi standard non polar	33892256
Litcubinine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	3027.6	Semi standard non polar	33892256
Litcubinine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC(O)=C(O)C=C3[N+]1(C)CC2	3290.4	Semi standard non polar	33892256
Litcubinine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)C1CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3[N+]1(C)CC2	3317.5	Semi standard non polar	33892256
Litcubinine,1TBDMS,isomer #3	COC1=CC2=C(C=C1O)C1CC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3302.6	Semi standard non polar	33892256
Litcubinine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3[N+]1(C)CC2	3483.4	Semi standard non polar	33892256
Litcubinine,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3476.2	Semi standard non polar	33892256
Litcubinine,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)C1CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3512.6	Semi standard non polar	33892256
Litcubinine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3668.2	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 - Litcubinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0790000000-bff32bcba837755a57b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litcubinine GC-MS (3 TMS) - 70eV, Positive	splash10-0400-1012890000-fe40ab1665f942da2bf2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litcubinine 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 - Litcubinine 10V, Positive-QTOF	splash10-03di-0019000000-ce49956d5a0c331f2a69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubinine 20V, Positive-QTOF	splash10-000i-0292000000-a79a3e80f4152c3672af	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubinine 40V, Positive-QTOF	splash10-0596-0390000000-a154adf2de5194c8cda9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubinine 10V, Positive-QTOF	splash10-03di-0009000000-7c6568efb078161b6d48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubinine 20V, Positive-QTOF	splash10-03di-0379000000-de7d345208a1b7c86fa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubinine 40V, Positive-QTOF	splash10-01r6-0790000000-535fa28642c9a3648ba5	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010599

KNApSAcK ID

C00027560

Chemspider ID

35031948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85190560

PDB ID

Not Available

ChEBI ID

175041

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 Litcubinine (HMDB0032650)

MOL for HMDB0032650 (Litcubinine)

3D MOL for HMDB0032650 (Litcubinine)

3D SDF for HMDB0032650 (Litcubinine)

3D-SDF for HMDB0032650 (Litcubinine)

PDB for HMDB0032650 (Litcubinine)

3D PDB for HMDB0032650 (Litcubinine)

SMILES for HMDB0032650 (Litcubinine)

INCHI for HMDB0032650 (Litcubinine)

Structure for HMDB0032650 (Litcubinine)

3D Structure for HMDB0032650 (Litcubinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra