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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:31 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030220

Secondary Accession Numbers

HMDB30220

Metabolite Identification

Common Name

Laurotetanine

Description

Laurotetanine, also known as litsoeine, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Laurotetanine is a very strong basic compound (based on its pKa). Outside of the human body, laurotetanine has been detected, but not quantified in, cherimoya. This could make laurotetanine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030220
     RDKit          3D
Laurotetanine
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8677    0.5121   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.7786    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -1.2554    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.3833    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8304    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -2.1020    0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.9415    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998   -2.5222    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919   -3.3644    1.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -2.6584    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207   -1.7371    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341   -1.6631    1.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -1.2092    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.0417    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4974    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    1.7846   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    2.2303   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064    3.5462   -0.9869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    4.4041   -1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261    1.3708   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    1.9688   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6619    1.9944   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    0.0841    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856   -0.3716    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.6215   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    1.3088    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9207    0.7203   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.5895   -0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -3.9444    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592   -4.2888    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -3.0483    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -3.5579    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -2.1836   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -2.6551    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -1.0918    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443   -2.0593    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074   -0.1150   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129    0.8599    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    2.4361   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    4.6741   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    5.3513   -1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    3.9490   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    2.3486   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    2.5447   -2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.9227   -2.4005 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  8  3  1  0
 24 11  1  0
 23  5  1  0
 24 15  2  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
M  END


  Mrv0541 05061305052D          

 24 27  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  5  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  1  1  0  0  0  0
 22 15  1  0  0  0  0
 23  2  1  0  0  0  0
 23 16  1  0  0  0  0
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030220

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34

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

> <INCHI_KEY>
GVVXPMORGFYVOO-UHFFFAOYSA-N

> <FORMULA>
C19H21NO4

> <MOLECULAR_WEIGHT>
327.3743

> <EXACT_MASS>
327.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.63988161541483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.9725220313263767

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.948030491241806

> <JCHEM_PKA_STRONGEST_BASIC>
9.229503149120427

> <JCHEM_POLAR_SURFACE_AREA>
59.95

> <JCHEM_REFRACTIVITY>
92.1021

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030220
     RDKit          3D
Laurotetanine
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8677    0.5121   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.7786    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -1.2554    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.3833    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8304    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -2.1020    0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.9415    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998   -2.5222    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919   -3.3644    1.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -2.6584    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207   -1.7371    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341   -1.6631    1.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -1.2092    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.0417    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4974    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    1.7846   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    2.2303   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064    3.5462   -0.9869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    4.4041   -1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261    1.3708   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    1.9688   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6619    1.9944   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    0.0841    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856   -0.3716    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.6215   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    1.3088    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9207    0.7203   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.5895   -0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -3.9444    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592   -4.2888    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -3.0483    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -3.5579    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -2.1836   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -2.6551    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -1.0918    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443   -2.0593    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074   -0.1150   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129    0.8599    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    2.4361   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    4.6741   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    5.3513   -1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    3.9490   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    2.3486   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    2.5447   -2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.9227   -2.4005 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  8  3  1  0
 24 11  1  0
 23  5  1  0
 24 15  2  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  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      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5   10                                                       
CONECT    5    4   20                                                       
CONECT    6   11   13                                                       
CONECT    7   11   14                                                       
CONECT    8   10   16                                                       
CONECT    9   12   15                                                       
CONECT   10    4    8   17                                                  
CONECT   11    6    7   12                                                  
CONECT   12    9   11   18                                                  
CONECT   13    6   17   20                                                  
CONECT   14    7   15   21                                                  
CONECT   15    9   14   22                                                  
CONECT   16    8   19   23                                                  
CONECT   17   10   13   18                                                  
CONECT   18   12   17   19                                                  
CONECT   19   16   18   24                                                  
CONECT   20    5   13                                                       
CONECT   21   14                                                            
CONECT   22    1   15                                                       
CONECT   23    2   16                                                       
CONECT   24    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0030220
HETATM    1  C1  UNL     1       4.868   0.512  -0.239  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.631  -0.779   0.225  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.348  -1.255   0.410  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.277  -0.383   0.111  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.009  -0.830   0.283  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.723  -2.102   0.742  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.807  -2.942   1.031  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.100  -2.522   0.866  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.192  -3.364   1.154  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.629  -2.658   0.977  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.721  -1.737   0.635  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.734  -1.663   1.698  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.954  -1.209   1.099  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.862   0.042   0.298  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.473   0.497   0.056  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.248   1.785  -0.348  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.967   2.230  -0.578  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.806   3.546  -0.987  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.909   4.404  -1.164  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.126   1.371  -0.399  1.00  0.00           C  
HETATM   21  O4  UNL     1       1.325   1.969  -0.681  1.00  0.00           O  
HETATM   22  C17 UNL     1       1.662   1.994  -2.114  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.127   0.084   0.013  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.386  -0.372   0.240  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.302   0.622  -1.210  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.491   1.309   0.419  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.921   0.720  -0.457  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.532   0.590  -0.198  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.612  -3.944   1.392  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.959  -4.289   1.487  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.729  -3.048   2.026  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.690  -3.558   0.281  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.321  -2.184  -0.233  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.887  -2.655   2.002  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.737  -1.092   1.904  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.344  -2.059   0.474  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.407  -0.115  -0.663  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.413   0.860   0.814  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.121   2.436  -0.479  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.297   4.674  -0.145  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.637   5.351  -1.655  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.709   3.949  -1.782  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.695   2.349  -2.238  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.904   2.545  -2.666  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.624   0.923  -2.401  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   23
CONECT    6    7   10
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   30
CONECT   10   11   31   32
CONECT   11   12   24   33
CONECT   12   13   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   24   24
CONECT   16   17   17   39
CONECT   17   18   20
CONECT   18   19
CONECT   19   40   41   42
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   43   44   45
CONECT   23   24
END

HMDB0030220
     RDKit          3D
Laurotetanine
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8677    0.5121   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.7786    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -1.2554    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.3833    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8304    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -2.1020    0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.9415    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998   -2.5222    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919   -3.3644    1.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -2.6584    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207   -1.7371    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341   -1.6631    1.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -1.2092    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.0417    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4974    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    1.7846   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    2.2303   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064    3.5462   -0.9869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    4.4041   -1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261    1.3708   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    1.9688   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6619    1.9944   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    0.0841    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856   -0.3716    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.6215   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    1.3088    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9207    0.7203   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.5895   -0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -3.9444    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592   -4.2888    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -3.0483    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -3.5579    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -2.1836   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -2.6551    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -1.0918    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443   -2.0593    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074   -0.1150   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129    0.8599    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    2.4361   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    4.6741   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    5.3513   -1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    3.9490   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    2.3486   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    2.5447   -2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.9227   -2.4005 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  8  3  1  0
 24 11  1  0
 23  5  1  0
 24 15  2  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Laurotetanine	HMDB
6Aalpha 1,2,10-trimethoxy--noraporphin-9-ol	HMDB
9-Hydroxy-1,2,10-trimethoxynoraporphine	HMDB
Laurotetanin	HMDB
Litsoeine	HMDB
Litsoene	HMDB
Laurotetanine	MeSH
1,2,10-Trimethoxy-9-hydroxynoraporphine	MeSH

Chemical Formula

C₁₉H₂₁NO₄

Average Molecular Weight

327.3743

Monoisotopic Molecular Weight

327.147058165

IUPAC Name

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

Traditional Name

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

CAS Registry Number

128-76-7

SMILES

COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34

InChI Identifier

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

InChI Key

GVVXPMORGFYVOO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Tetrahydroisoquinoline
Quinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030220)
Cytoplasm (HMDB: HMDB0030220)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030220)

Source

Endogenous

Endogenous (HMDB: HMDB0030220)

Plant

Plant (HMDB: HMDB0030220)

Exogenous

Food

Food (HMDB: HMDB0030220)

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 °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	0.038 g/L	ALOGPS
logP	1.61	ALOGPS
logP	1.97	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.1 m³·mol⁻¹	ChemAxon
Polarizability	35.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.226	31661259
DarkChem	[M-H]-	175.717	31661259
DeepCCS	[M-2H]-	210.54	30932474
DeepCCS	[M+Na]+	186.727	30932474
AllCCS	[M+H]+	177.7	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	184.0	32859911
AllCCS	[M+HCOO]-	183.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laurotetanine	COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34	4285.1	Standard polar	33892256
Laurotetanine	COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34	2793.8	Standard non polar	33892256
Laurotetanine	COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34	2984.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Laurotetanine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(OC)C(OC)=C3	2894.8	Semi standard non polar	33892256
Laurotetanine,1TMS,isomer #2	COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C	2854.1	Semi standard non polar	33892256
Laurotetanine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C	2810.5	Semi standard non polar	33892256
Laurotetanine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C	2998.7	Standard non polar	33892256
Laurotetanine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(OC)C(OC)=C3	3134.7	Semi standard non polar	33892256
Laurotetanine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3088.4	Semi standard non polar	33892256
Laurotetanine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3242.1	Semi standard non polar	33892256
Laurotetanine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3441.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Laurotetanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0093000000-4a2d9a46dc0f5b9fa88a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laurotetanine GC-MS (1 TMS) - 70eV, Positive	splash10-05ai-1019000000-c62af0509c8ab6844c08	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laurotetanine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Laurotetanine , positive-QTOF	splash10-00m0-0190000000-65f5217cc745d745c6bf	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 10V, Positive-QTOF	splash10-004i-0019000000-6e4c101a52ba3c805269	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 20V, Positive-QTOF	splash10-004i-0059000000-d66fc144960738730cb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 40V, Positive-QTOF	splash10-001l-0190000000-36b048ab4b509c2c1b92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 10V, Negative-QTOF	splash10-004i-0009000000-bad89b6504d850983aee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 20V, Negative-QTOF	splash10-01t9-0029000000-cc0b1a9f23be31e894ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 40V, Negative-QTOF	splash10-01q9-0090000000-b9aa2cd54c822be08387	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 10V, Negative-QTOF	splash10-004i-0009000000-82e8b7e0c70cdc0f9fe6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 20V, Negative-QTOF	splash10-004i-0009000000-610458ce85bb917f5cc4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 40V, Negative-QTOF	splash10-00dl-0095000000-5d3de9a7d15a236542b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 10V, Positive-QTOF	splash10-004i-0009000000-354160c39518aa1987e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 20V, Positive-QTOF	splash10-004i-0019000000-7b28233b2a0c3889df0a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurotetanine 40V, Positive-QTOF	splash10-0gxx-0092000000-92ccc2aebefeed83a873	2021-09-24	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

FDB002039

KNApSAcK ID

C00027409

Chemspider ID

235026

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

267400

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 Laurotetanine (HMDB0030220)

MOL for HMDB0030220 (Laurotetanine)

3D MOL for HMDB0030220 (Laurotetanine)

3D SDF for HMDB0030220 (Laurotetanine)

3D-SDF for HMDB0030220 (Laurotetanine)

PDB for HMDB0030220 (Laurotetanine)

3D PDB for HMDB0030220 (Laurotetanine)

SMILES for HMDB0030220 (Laurotetanine)

INCHI for HMDB0030220 (Laurotetanine)

Structure for HMDB0030220 (Laurotetanine)

3D Structure for HMDB0030220 (Laurotetanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra