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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:30 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030217

Secondary Accession Numbers

HMDB30217

Metabolite Identification

Common Name

Launobine

Description

Launobine 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. Launobine has been detected, but not quantified in, herbs and spices and sweet bays (Laurus nobilis). This could make launobine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Launobine.

Structure

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

HMDB0030217
     RDKit          3D
Launobine
 40 44  0  0  0  0  0  0  0  0999 V2000
   -5.5564   -0.8807   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341   -0.0244   -0.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.5056   -0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9963   -1.8754   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -2.4149    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6356   -1.5845    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -0.2081    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0507    0.3391   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    1.6548   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017    0.6221    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    1.9946    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    2.7508    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    2.1221    0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    0.7746    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356    0.0210    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464   -1.4308    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.2764    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -1.8719   -0.3952 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -1.0211   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -0.0040    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096    4.0817    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    4.0775   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    2.8848   -0.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -0.2956   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.5540    0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4739   -1.4772   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8654   -2.5392   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -3.4907    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    2.0118   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.7200    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5877    1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -2.9651    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.9981   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -2.0739   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -1.6322   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366   -0.4287   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815   -0.5676    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410    0.6471    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    4.0774   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209    4.9284   -0.1416 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv0541 05061305052D          

 23 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
    4.2868   -1.6500    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
    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    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
    1.4289    0.0000    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   -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
    3.5724   -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
    4.2868    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
    4.2868    0.8250    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
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21 12  1  0  0  0  0
 22  8  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030217

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(CC3NCCC4=CC5=C(OCO5)C2=C34)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO4/c1-21-12-3-2-9-6-11-14-10(4-5-19-11)7-13-18(23-8-22-13)16(14)15(9)17(12)20/h2-3,7,11,19-20H,4-6,8H2,1H3

> <INCHI_KEY>
JIFBCUOVFPCZEW-UHFFFAOYSA-N

> <FORMULA>
C18H17NO4

> <MOLECULAR_WEIGHT>
311.3319

> <EXACT_MASS>
311.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.93356988226782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.7773065373469032

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.136731771004351

> <JCHEM_PKA_STRONGEST_BASIC>
9.833106897925633

> <JCHEM_POLAR_SURFACE_AREA>
59.95

> <JCHEM_REFRACTIVITY>
84.9426

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030217
     RDKit          3D
Launobine
 40 44  0  0  0  0  0  0  0  0999 V2000
   -5.5564   -0.8807   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341   -0.0244   -0.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.5056   -0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9963   -1.8754   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -2.4149    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6356   -1.5845    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -0.2081    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0507    0.3391   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    1.6548   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017    0.6221    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    1.9946    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    2.7508    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    2.1221    0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    0.7746    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356    0.0210    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464   -1.4308    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.2764    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -1.8719   -0.3952 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -1.0211   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -0.0040    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096    4.0817    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    4.0775   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    2.8848   -0.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -0.2956   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.5540    0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4739   -1.4772   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8654   -2.5392   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -3.4907    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    2.0118   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.7200    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5877    1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -2.9651    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.9981   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -2.0739   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -1.6322   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366   -0.4287   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815   -0.5676    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410    0.6471    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    4.0774   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209    4.9284   -0.1416 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    9                                                       
CONECT    3    2   12                                                       
CONECT    4    5   10                                                       
CONECT    5    4   19                                                       
CONECT    6    9   11                                                       
CONECT    7   10   13                                                       
CONECT    8   22   23                                                       
CONECT    9    2    6   15                                                  
CONECT   10    4    7   14                                                  
CONECT   11    6   14   19                                                  
CONECT   12    3   17   21                                                  
CONECT   13    7   18   22                                                  
CONECT   14   10   11   16                                                  
CONECT   15    9   16   17                                                  
CONECT   16   14   15   18                                                  
CONECT   17   12   15   20                                                  
CONECT   18   13   16   23                                                  
CONECT   19    5   11                                                       
CONECT   20   17                                                            
CONECT   21    1   12                                                       
CONECT   22    8   13                                                       
CONECT   23    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0030217
HETATM    1  C1  UNL     1      -5.556  -0.881  -0.410  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.434  -0.024  -0.319  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.142  -0.506  -0.154  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.996  -1.875  -0.080  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.753  -2.415   0.082  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.636  -1.584   0.173  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.809  -0.208   0.097  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.051   0.339  -0.065  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.298   1.655  -0.147  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.402   0.622   0.214  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.301   1.995   0.133  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.489   2.751   0.238  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.698   2.122   0.415  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.791   0.775   0.494  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.636   0.021   0.394  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.846  -1.431   0.508  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.667  -2.276   0.336  1.00  0.00           C  
HETATM   18  N1  UNL     1       2.897  -1.872  -0.395  1.00  0.00           N  
HETATM   19  C16 UNL     1       4.047  -1.021  -0.437  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.041  -0.004   0.682  1.00  0.00           C  
HETATM   21  O3  UNL     1       1.110   4.082   0.124  1.00  0.00           O  
HETATM   22  C18 UNL     1      -0.163   4.078  -0.547  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.722   2.885  -0.035  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.497  -0.296  -0.375  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.530  -1.554   0.493  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.474  -1.477  -1.337  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.865  -2.539  -0.151  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.635  -3.491   0.140  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.236   2.012  -0.267  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.592   2.720   0.492  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.238  -1.588   1.550  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.555  -2.965   1.237  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.830  -2.998  -0.509  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.504  -2.074  -1.322  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.971  -1.632  -0.373  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.037  -0.429  -1.394  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.981  -0.568   1.643  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.941   0.647   0.647  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.055   4.077  -1.632  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.721   4.928  -0.142  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   28
CONECT    6    7   17
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   29
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   21
CONECT   13   14   30
CONECT   14   15   15   20
CONECT   15   16
CONECT   16   17   18   31
CONECT   17   32   33
CONECT   18   19   34
CONECT   19   20   35   36
CONECT   20   37   38
CONECT   21   22
CONECT   22   23   39   40
END

HMDB0030217
     RDKit          3D
Launobine
 40 44  0  0  0  0  0  0  0  0999 V2000
   -5.5564   -0.8807   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341   -0.0244   -0.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.5056   -0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9963   -1.8754   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -2.4149    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6356   -1.5845    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -0.2081    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0507    0.3391   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    1.6548   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017    0.6221    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    1.9946    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    2.7508    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    2.1221    0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    0.7746    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356    0.0210    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464   -1.4308    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.2764    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -1.8719   -0.3952 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -1.0211   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -0.0040    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096    4.0817    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    4.0775   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    2.8848   -0.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -0.2956   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.5540    0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4739   -1.4772   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8654   -2.5392   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -3.4907    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    2.0118   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.7200    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5877    1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -2.9651    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.9981   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -2.0739   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -1.6322   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366   -0.4287   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815   -0.5676    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410    0.6471    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    4.0774   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209    4.9284   -0.1416 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Launobine	HMDB
11-Hydroxy-10-methoxy-1,2-methylenedioxynoraporphine	HMDB
Norbulbocapnine	HMDB

Chemical Formula

C₁₈H₁₇NO₄

Average Molecular Weight

311.3319

Monoisotopic Molecular Weight

311.115758037

IUPAC Name

17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol

Traditional Name

17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol

CAS Registry Number

20497-21-6

SMILES

COC1=C(O)C2=C(CC3NCCC4=CC5=C(OCO5)C2=C34)C=C1

InChI Identifier

InChI=1S/C18H17NO4/c1-21-12-3-2-9-6-11-14-10(4-5-19-11)7-13-18(23-8-22-13)16(14)15(9)17(12)20/h2-3,7,11,19-20H,4-6,8H2,1H3

InChI Key

JIFBCUOVFPCZEW-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
1-naphthol
Naphthalene
Tetrahydroisoquinoline
Quinoline
Benzodioxole
Anisole
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Azacycle
Ether
Secondary aliphatic amine
Acetal
Oxacycle
Secondary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen 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: HMDB0030217)
Cytoplasm (HMDB: HMDB0030217)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030217)

Source

Endogenous

Endogenous (HMDB: HMDB0030217)

Plant

Plant (HMDB: HMDB0030217)

Exogenous

Food

Food (HMDB: HMDB0030217)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030217)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	214 - 215 °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	0.2 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.78	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	9.83	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	1	ChemAxon
Refractivity	84.94 m³·mol⁻¹	ChemAxon
Polarizability	32.93 Å³	ChemAxon
Number of Rings	5	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]+	173.234	31661259
DarkChem	[M-H]-	171.378	31661259
DeepCCS	[M-2H]-	219.664	30932474
DeepCCS	[M+Na]+	194.995	30932474
AllCCS	[M+H]+	173.2	32859911
AllCCS	[M+H-H2O]+	169.8	32859911
AllCCS	[M+NH4]+	176.3	32859911
AllCCS	[M+Na]+	177.2	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.2	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3559 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1122.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	347.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	330.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	589.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	749.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	336.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1054.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	441.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	93.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Launobine	COC1=C(O)C2=C(CC3NCCC4=CC5=C(OCO5)C2=C34)C=C1	4123.3	Standard polar	33892256
Launobine	COC1=C(O)C2=C(CC3NCCC4=CC5=C(OCO5)C2=C34)C=C1	2705.0	Standard non polar	33892256
Launobine	COC1=C(O)C2=C(CC3NCCC4=CC5=C(OCO5)C2=C34)C=C1	3074.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Launobine,1TMS,isomer #1	COC1=CC=C2CC3NCCC4=C3C(=C3OCOC3=C4)C2=C1O[Si](C)(C)C	2921.1	Semi standard non polar	33892256
Launobine,1TMS,isomer #2	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O)CCN3[Si](C)(C)C	2851.5	Semi standard non polar	33892256
Launobine,2TMS,isomer #1	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O[Si](C)(C)C)CCN3[Si](C)(C)C	2847.5	Semi standard non polar	33892256
Launobine,2TMS,isomer #1	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O[Si](C)(C)C)CCN3[Si](C)(C)C	2938.0	Standard non polar	33892256
Launobine,1TBDMS,isomer #1	COC1=CC=C2CC3NCCC4=C3C(=C3OCOC3=C4)C2=C1O[Si](C)(C)C(C)(C)C	3147.2	Semi standard non polar	33892256
Launobine,1TBDMS,isomer #2	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O)CCN3[Si](C)(C)C(C)(C)C	3074.7	Semi standard non polar	33892256
Launobine,2TBDMS,isomer #1	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O[Si](C)(C)C(C)(C)C)CCN3[Si](C)(C)C(C)(C)C	3270.3	Semi standard non polar	33892256
Launobine,2TBDMS,isomer #1	COC1=CC=C2CC3C4=C(C=C5OCOC5=C4C2=C1O[Si](C)(C)C(C)(C)C)CCN3[Si](C)(C)C(C)(C)C	3402.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Launobine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-0190000000-7a6e49747571c244fe1e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Launobine GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-1139000000-cf62cfc78cdbd7525e51	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Launobine 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 - Launobine 10V, Positive-QTOF	splash10-03di-0029000000-49ebd1aaa8fac7cdcb12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 20V, Positive-QTOF	splash10-03di-0295000000-d50d92ba37362c0b50be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 40V, Positive-QTOF	splash10-0fl3-0690000000-0ef0e941a1a83e22b4fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 10V, Negative-QTOF	splash10-03di-0019000000-c59aed5cdc046a0b8354	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 20V, Negative-QTOF	splash10-03di-0069000000-638ce4a1bf434b2568a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 40V, Negative-QTOF	splash10-01vx-0190000000-15d546c5e7e03ba77b5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 10V, Negative-QTOF	splash10-03di-0009000000-43e89ef889a2eb4f124e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 20V, Negative-QTOF	splash10-03di-0059000000-3781b0776bfb7a8ff157	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 40V, Negative-QTOF	splash10-0a4i-0059000000-13060a396ca4720aaee9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 10V, Positive-QTOF	splash10-03di-0009000000-4631b5d1b4d93faf70b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 20V, Positive-QTOF	splash10-03di-0009000000-65f473f2f52304e05f3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Launobine 40V, Positive-QTOF	splash10-0w39-0091000000-bb915aca7728f0fe2ca0	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

FDB002036

KNApSAcK ID

C00027407

Chemspider ID

154253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318956

PDB ID

Not Available

ChEBI ID

174971

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818041

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 Launobine (HMDB0030217)

MOL for HMDB0030217 (Launobine)

3D MOL for HMDB0030217 (Launobine)

3D SDF for HMDB0030217 (Launobine)

3D-SDF for HMDB0030217 (Launobine)

PDB for HMDB0030217 (Launobine)

3D PDB for HMDB0030217 (Launobine)

SMILES for HMDB0030217 (Launobine)

INCHI for HMDB0030217 (Launobine)

Structure for HMDB0030217 (Launobine)

3D Structure for HMDB0030217 (Launobine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra