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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:54 UTC

Update Date

2022-03-07 02:53:14 UTC

HMDB ID

HMDB0032110

Secondary Accession Numbers

HMDB32110

Metabolite Identification

Common Name

Litcubine

Description

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

Structure

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

HMDB0032110
     RDKit          3D
Litcubine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.9242    1.6570   -1.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    1.8157   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.5320   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786    1.0972   -1.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.8447   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896    1.0030    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079    1.4334    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    1.6900    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    2.1233    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    0.6922    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    0.4096    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888   -0.3128    1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4890    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1219   -1.2306    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649   -1.4022    1.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6549   -0.8153    3.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8830   -1.8212    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847   -2.5836   -0.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497   -1.6499   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -0.9043    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -0.6095   -0.3865 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5714   -1.6103    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.4333   -1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.3853   -2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362    2.1340   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334    0.5710   -2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    2.0987   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.9769   -2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.5542    2.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094    2.3342    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.4002   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    1.3517    2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206   -0.2431    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.0293    2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3544    0.2325    3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -1.4185    3.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7703   -0.8722    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605   -2.6717   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -2.1304   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -2.3931   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -1.2039    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940   -2.1554    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452   -0.0353   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860   -1.4538   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -0.1586   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    1.2907   -2.7431 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
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 21 10  1  0
 24  5  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
M  CHG  1  21   1
M  END


  Mrv0541 05061306222D          

 24 27  0  0  0  0            999 V2000
    1.7213    1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913   -1.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.2489   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 11  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18  7  1  0  0  0  0
 18 16  2  0  0  0  0
 19  8  1  0  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20  5  1  0  0  0  0
 20 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
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
HMDB0032110

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO4/c1-20-5-4-11-7-18(23-2)16(21)9-13(11)15(20)6-12-8-19(24-3)17(22)10-14(12)20/h7-10,15H,4-6H2,1-3H3,(H-,21,22)/p+1

> <INCHI_KEY>
CWKRVCVOEADAEH-UHFFFAOYSA-O

> <FORMULA>
C19H22NO4

> <MOLECULAR_WEIGHT>
328.3823

> <EXACT_MASS>
328.154883197

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.2556635851015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,13-dihydroxy-5,14-dimethoxy-10-methyl-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-10-ium

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
-1.0255059354717457

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.422391922894831

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.639510924517481

> <JCHEM_PKA_STRONGEST_BASIC>
-4.594911479623322

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
103.46950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,13-dihydroxy-5,14-dimethoxy-10-methyl-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-10-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032110
     RDKit          3D
Litcubine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.9242    1.6570   -1.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    1.8157   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.5320   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786    1.0972   -1.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.8447   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896    1.0030    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079    1.4334    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    1.6900    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    2.1233    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    0.6922    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    0.4096    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888   -0.3128    1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4890    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1219   -1.2306    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649   -1.4022    1.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6549   -0.8153    3.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8830   -1.8212    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847   -2.5836   -0.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497   -1.6499   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -0.9043    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -0.6095   -0.3865 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5714   -1.6103    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.4333   -1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.3853   -2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362    2.1340   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334    0.5710   -2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    2.0987   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.9769   -2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.5542    2.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094    2.3342    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.4002   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    1.3517    2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206   -0.2431    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.0293    2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3544    0.2325    3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -1.4185    3.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7703   -0.8722    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605   -2.6717   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -2.1304   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -2.3931   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -1.2039    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940   -2.1554    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452   -0.0353   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860   -1.4538   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -0.1586   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    1.2907   -2.7431 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
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 21 10  1  0
 24  5  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
M  CHG  1  21   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       3.213   3.074   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.028  -0.341   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.477  -2.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.418   3.345   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.070  -0.607   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.800   2.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.261  -0.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.416  -0.606   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       4.188   1.881   0.000  0.00  0.00           N+1
HETATM   21  O   UNK     0       9.798  -1.805   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.257   2.435   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.183   0.946   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.404  -0.642   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5   11                                                       
CONECT    5    4   20                                                       
CONECT    6   12   15                                                       
CONECT    7   11   18                                                       
CONECT    8   12   19                                                       
CONECT    9   13   16                                                       
CONECT   10   14   17                                                       
CONECT   11    4    7   13                                                  
CONECT   12    6    8   14                                                  
CONECT   13    9   11   15                                                  
CONECT   14   10   12   20                                                  
CONECT   15    6   13   20                                                  
CONECT   16    9   18   21                                                  
CONECT   17   10   19   22                                                  
CONECT   18    7   16   23                                                  
CONECT   19    8   17   24                                                  
CONECT   20    1    5   14   15                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    2   18                                                       
CONECT   24    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0032110
HETATM    1  C1  UNL     1       5.924   1.657  -1.795  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.346   1.816  -0.518  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.998   1.532  -0.358  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.179   1.097  -1.393  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.851   0.845  -1.120  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.290   1.003   0.139  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.108   1.433   1.156  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.442   1.690   0.893  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.239   2.123   1.944  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.126   0.692   0.252  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.640   0.410   1.634  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.889  -0.313   1.276  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.115  -0.489   1.864  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.122  -1.231   1.288  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.365  -1.402   1.896  1.00  0.00           O  
HETATM   16  C13 UNL     1      -5.655  -0.815   3.151  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.883  -1.821   0.064  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.885  -2.584  -0.553  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.650  -1.650  -0.538  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.655  -0.904   0.055  1.00  0.00           C  
HETATM   21  N1  UNL     1      -0.333  -0.609  -0.387  1.00  0.00           N1+
HETATM   22  C17 UNL     1       0.571  -1.610   0.091  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.189  -0.433  -1.782  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.981   0.385  -2.210  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.936   2.134  -1.844  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.033   0.571  -2.003  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.312   2.099  -2.588  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.622   0.977  -2.366  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.664   1.554   2.131  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.209   2.334   1.858  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.801   1.400  -0.237  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.875   1.352   2.182  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.021  -0.243   2.228  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.340  -0.029   2.845  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.354   0.232   3.228  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.223  -1.419   3.991  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.770  -0.872   3.299  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.761  -2.672  -0.066  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.484  -2.130  -1.512  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.645  -2.393  -0.718  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.575  -1.204   0.221  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.194  -2.155   0.980  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.145  -0.035  -2.190  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.086  -1.454  -2.249  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.614  -0.159  -2.962  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.590   1.291  -2.743  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   10
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   30
CONECT   10   11   21   31
CONECT   11   12   32   33
CONECT   12   13   13   20
CONECT   13   14   34
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   35   36   37
CONECT   17   18   19
CONECT   18   38
CONECT   19   20   20   39
CONECT   20   21
CONECT   21   22   23
CONECT   22   40   41   42
CONECT   23   24   43   44
CONECT   24   45   46
END

HMDB0032110
     RDKit          3D
Litcubine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.9242    1.6570   -1.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    1.8157   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.5320   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786    1.0972   -1.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.8447   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896    1.0030    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079    1.4334    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    1.6900    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    2.1233    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    0.6922    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    0.4096    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888   -0.3128    1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4890    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1219   -1.2306    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649   -1.4022    1.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6549   -0.8153    3.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8830   -1.8212    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847   -2.5836   -0.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497   -1.6499   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -0.9043    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -0.6095   -0.3865 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5714   -1.6103    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.4333   -1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.3853   -2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362    2.1340   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334    0.5710   -2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    2.0987   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.9769   -2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.5542    2.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094    2.3342    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.4002   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    1.3517    2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206   -0.2431    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.0293    2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3544    0.2325    3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -1.4185    3.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7703   -0.8722    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605   -2.6717   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -2.1304   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -2.3931   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -1.2039    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940   -2.1554    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452   -0.0353   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860   -1.4538   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -0.1586   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    1.2907   -2.7431 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
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 21 10  1  0
 24  5  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
M  CHG  1  21   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂NO₄

Average Molecular Weight

328.3823

Monoisotopic Molecular Weight

328.154883197

IUPAC Name

4,13-dihydroxy-5,14-dimethoxy-10-methyl-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-10-ium

Traditional Name

4,13-dihydroxy-5,14-dimethoxy-10-methyl-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-10-ium

CAS Registry Number

172924-22-0

SMILES

COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23C)=C1

InChI Identifier

InChI=1S/C19H21NO4/c1-20-5-4-11-7-18(23-2)16(21)9-13(11)15(20)6-12-8-19(24-3)17(22)10-14(12)20/h7-10,15H,4-6H2,1-3H3,(H-,21,22)/p+1

InChI Key

CWKRVCVOEADAEH-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
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Quaternary ammonium salt
Ether
Azacycle
Organic nitrogen compound
Amine
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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: HMDB0032110)
Cytoplasm (HMDB: HMDB0032110)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032110)

Source

Endogenous

Endogenous (HMDB: HMDB0032110)

Plant

Plant (HMDB: HMDB0032110)

Exogenous

Food

Food (HMDB: HMDB0032110)

Fruit

Fruits (FooDB: FOOD00871)

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	449.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.004 g/L	ALOGPS
logP	1.97	ALOGPS
logP	-1	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.47 m³·mol⁻¹	ChemAxon
Polarizability	36.26 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]+	175.606	31661259
DarkChem	[M-H]-	174.704	31661259
DeepCCS	[M-2H]-	220.138	30932474
DeepCCS	[M+Na]+	196.238	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	176.1	32859911
AllCCS	[M+NH4]+	182.0	32859911
AllCCS	[M+Na]+	182.8	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	188.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Litcubine	COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23C)=C1	4629.0	Standard polar	33892256
Litcubine	COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23C)=C1	2763.8	Standard non polar	33892256
Litcubine	COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23C)=C1	2974.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Litcubine,1TMS,isomer #1	COC1=CC2=C(C=C1O)C1CC3=CC(OC)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	2991.3	Semi standard non polar	33892256
Litcubine,1TMS,isomer #2	COC1=CC2=C(C=C1O)[N+]1(C)CCC3=CC(OC)=C(O[Si](C)(C)C)C=C3C1C2	2983.4	Semi standard non polar	33892256
Litcubine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC(OC)=C(O[Si](C)(C)C)C=C3[N+]1(C)CC2	2970.0	Semi standard non polar	33892256
Litcubine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O)C1CC3=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3268.5	Semi standard non polar	33892256
Litcubine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)[N+]1(C)CCC3=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3C1C2	3254.1	Semi standard non polar	33892256
Litcubine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3[N+]1(C)CC2	3422.3	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 - Litcubine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-0294000000-1ac175ef03922f08263b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litcubine GC-MS (2 TMS) - 70eV, Positive	splash10-0a4j-3064900000-108168d61f5ce4bdfcbe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litcubine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litcubine 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 - Litcubine 10V, Positive-QTOF	splash10-004i-0009000000-8b5e63345d07a6fbe482	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubine 20V, Positive-QTOF	splash10-0fba-0049000000-9862fe93f4f1f89b1436	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubine 40V, Positive-QTOF	splash10-0k9x-0190000000-ba9ed2a140f67e01fc54	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubine 10V, Positive-QTOF	splash10-004i-0009000000-354160c39518aa1987e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubine 20V, Positive-QTOF	splash10-004i-0439000000-331cda5dc98887ea44a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litcubine 40V, Positive-QTOF	splash10-002f-0692000000-a160940143c43a2541cb	2021-09-24	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

FDB008832

KNApSAcK ID

C00027559

Chemspider ID

35031947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85243417

PDB ID

Not Available

ChEBI ID

169824

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1829761

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 Litcubine (HMDB0032110)

MOL for HMDB0032110 (Litcubine)

3D MOL for HMDB0032110 (Litcubine)

3D SDF for HMDB0032110 (Litcubine)

3D-SDF for HMDB0032110 (Litcubine)

PDB for HMDB0032110 (Litcubine)

3D PDB for HMDB0032110 (Litcubine)

SMILES for HMDB0032110 (Litcubine)

INCHI for HMDB0032110 (Litcubine)

Structure for HMDB0032110 (Litcubine)

3D Structure for HMDB0032110 (Litcubine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra