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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:36:22 UTC

Update Date

2022-03-07 02:56:49 UTC

HMDB ID

HMDB0040974

Secondary Accession Numbers

HMDB40974

Metabolite Identification

Common Name

Laurolitsine

Description

Laurolitsine 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. Based on a literature review a significant number of articles have been published on Laurolitsine.

Structure

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

HMDB0040974
     RDKit          3D
Laurolitsine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.6388    1.1092   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4384   -0.2638   -0.5028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661   -0.8041   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    0.0766   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333   -0.4371   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024   -1.8025   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -2.6618   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.1721   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -3.0130   -0.5956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -2.4721   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8639   -1.5887   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7832   -1.8077   -1.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538   -1.2525   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -0.0425   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6972    0.6660   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022    2.0298    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476    2.5868    0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    3.9579    0.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    1.8013   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    2.4760   -0.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    2.8818    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    0.4469   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.1563   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    1.6883   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    1.5709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7221    1.3125   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    1.0940   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -3.7337   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -3.9944   -0.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -3.1888   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -3.1374    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.8233    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -2.8427   -1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957   -1.0443   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -2.0442   -0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    0.7056   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2120   -0.3016    1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    2.6333    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    4.5584    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689    2.9998    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    2.1322    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104    3.8573    1.4884 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 22  5  1  0
 23 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
M  END


  Mrv0541 05061312172D          

 23 26  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    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
    1.4289    0.8250    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
    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
    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   -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
    2.1434    2.0625    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
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  2  0  0  0  0
 18 17  1  0  0  0  0
 19  4  1  0  0  0  0
 19 12  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 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040974

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
KYVJVURXKAZJRK-UHFFFAOYSA-N

> <FORMULA>
C18H19NO4

> <MOLECULAR_WEIGHT>
313.3478

> <EXACT_MASS>
313.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.55471496103806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.6697153718633737

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.291002193820411

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.690188133971612

> <JCHEM_PKA_STRONGEST_BASIC>
9.089406204954987

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
87.61979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040974
     RDKit          3D
Laurolitsine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.6388    1.1092   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4384   -0.2638   -0.5028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661   -0.8041   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    0.0766   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333   -0.4371   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024   -1.8025   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -2.6618   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.1721   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -3.0130   -0.5956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -2.4721   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8639   -1.5887   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7832   -1.8077   -1.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538   -1.2525   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -0.0425   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6972    0.6660   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022    2.0298    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476    2.5868    0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    3.9579    0.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    1.8013   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    2.4760   -0.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    2.8818    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    0.4469   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.1563   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    1.6883   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    1.5709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7221    1.3125   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    1.0940   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -3.7337   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -3.9944   -0.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -3.1888   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -3.1374    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.8233    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -2.8427   -1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957   -1.0443   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -2.0442   -0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    0.7056   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2120   -0.3016    1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    2.6333    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    4.5584    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689    2.9998    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    2.1322    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104    3.8573    1.4884 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 22  5  1  0
 23 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  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   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   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  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   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      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   3.850   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       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4    9                                                       
CONECT    4    3   19                                                       
CONECT    5   10   12                                                       
CONECT    6    9   14                                                       
CONECT    7   10   13                                                       
CONECT    8   11   15                                                       
CONECT    9    3    6   16                                                  
CONECT   10    5    7   11                                                  
CONECT   11    8   10   17                                                  
CONECT   12    5   16   19                                                  
CONECT   13    7   15   20                                                  
CONECT   14    6   18   21                                                  
CONECT   15    8   13   22                                                  
CONECT   16    9   12   17                                                  
CONECT   17   11   16   18                                                  
CONECT   18   14   17   23                                                  
CONECT   19    4   12                                                       
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    1   15                                                       
CONECT   23    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0040974
HETATM    1  C1  UNL     1       4.639   1.109  -0.458  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.438  -0.264  -0.503  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.166  -0.804  -0.404  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.096   0.077  -0.259  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.833  -0.437  -0.158  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.602  -1.802  -0.200  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.691  -2.662  -0.347  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.967  -2.172  -0.449  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.071  -3.013  -0.596  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.695  -2.472  -0.100  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.864  -1.589  -0.108  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.783  -1.808  -1.231  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.054  -1.252  -0.886  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.016  -0.042  -0.022  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.697   0.666  -0.028  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.602   2.030   0.010  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.348   2.587   0.003  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.165   3.958   0.039  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.185   1.801  -0.040  1.00  0.00           C  
HETATM   20  O4  UNL     1       1.018   2.476  -0.029  1.00  0.00           O  
HETATM   21  C16 UNL     1       1.481   2.882   1.297  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.330   0.447  -0.081  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.582  -0.156  -0.073  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.062   1.688  -1.200  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.449   1.571   0.534  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.722   1.312  -0.694  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.338   1.094  -0.279  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.560  -3.734  -0.385  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.932  -3.994  -0.628  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.780  -3.189  -0.968  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.649  -3.137   0.813  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.488  -1.823   0.804  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.888  -2.843  -1.314  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.596  -1.044  -1.841  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.662  -2.044  -0.376  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.755   0.706  -0.403  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.212  -0.302   1.049  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.487   2.633   0.042  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.987   4.558   0.071  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.569   3.000   1.195  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.180   2.132   2.046  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.010   3.857   1.488  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   22
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   29
CONECT   10   11   30   31
CONECT   11   12   23   32
CONECT   12   13   33
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   23   23
CONECT   16   17   17   38
CONECT   17   18   19
CONECT   18   39
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   40   41   42
CONECT   22   23
END

HMDB0040974
     RDKit          3D
Laurolitsine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.6388    1.1092   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4384   -0.2638   -0.5028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661   -0.8041   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    0.0766   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333   -0.4371   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024   -1.8025   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -2.6618   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.1721   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -3.0130   -0.5956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -2.4721   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8639   -1.5887   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7832   -1.8077   -1.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538   -1.2525   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -0.0425   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6972    0.6660   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022    2.0298    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476    2.5868    0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    3.9579    0.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    1.8013   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    2.4760   -0.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    2.8818    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    0.4469   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.1563   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    1.6883   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    1.5709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7221    1.3125   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    1.0940   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -3.7337   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -3.9944   -0.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -3.1888   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -3.1374    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.8233    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -2.8427   -1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957   -1.0443   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -2.0442   -0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    0.7056   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2120   -0.3016    1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    2.6333    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    4.5584    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689    2.9998    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    2.1322    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104    3.8573    1.4884 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 22  5  1  0
 23 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,10-Dimethoxy-6a-alpha-noraporphine-2,9-diol	HMDB
2,9-Dihydroxy-1,10-dimethoxynoraporphine	HMDB
Dimethoxy-1,10 dihydroxy-2,9 nor-aporphine	HMDB
Laurolistine	HMDB
Norboldine	HMDB

Chemical Formula

C₁₈H₁₉NO₄

Average Molecular Weight

313.3478

Monoisotopic Molecular Weight

313.131408101

IUPAC Name

4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

Traditional Name

4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

CAS Registry Number

5890-18-6

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040974)
Cytoplasm (HMDB: HMDB0040974)

Source

Exogenous

Exogenous (HMDB: HMDB0040974)

Food

Food (HMDB: HMDB0040974)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040974)

Biological role

Nutrient (HMDB: HMDB0040974)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138 - 140 °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	0.25 g/L	ALOGPS
logP	1.73	ALOGPS
logP	1.67	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.62 m³·mol⁻¹	ChemAxon
Polarizability	33.55 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]+	172.447	31661259
DarkChem	[M-H]-	171.375	31661259
DeepCCS	[M-2H]-	208.241	30932474
DeepCCS	[M+Na]+	184.531	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.7	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laurolitsine	COC1=C(O)C=C2CC3NCCC4=CC(O)=C(OC)C(C2=C1)=C34	4201.7	Standard polar	33892256
Laurolitsine	COC1=C(O)C=C2CC3NCCC4=CC(O)=C(OC)C(C2=C1)=C34	2851.0	Standard non polar	33892256
Laurolitsine	COC1=C(O)C=C2CC3NCCC4=CC(O)=C(OC)C(C2=C1)=C34	3031.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Laurolitsine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(OC)C(O)=C3	2983.9	Semi standard non polar	33892256
Laurolitsine,1TMS,isomer #2	COC1=CC2=C(C=C1O)CC1NCCC3=C1C2=C(OC)C(O[Si](C)(C)C)=C3	2972.7	Semi standard non polar	33892256
Laurolitsine,1TMS,isomer #3	COC1=CC2=C(C=C1O)CC1C3=C(C=C(O)C(OC)=C23)CCN1[Si](C)(C)C	2896.9	Semi standard non polar	33892256
Laurolitsine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(OC)C(O[Si](C)(C)C)=C3	2875.0	Semi standard non polar	33892256
Laurolitsine,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(O)C(OC)=C23)CCN1[Si](C)(C)C	2821.9	Semi standard non polar	33892256
Laurolitsine,2TMS,isomer #3	COC1=CC2=C(C=C1O)CC1C3=C(C=C(O[Si](C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C	2820.7	Semi standard non polar	33892256
Laurolitsine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(O[Si](C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C	2819.6	Semi standard non polar	33892256
Laurolitsine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(O[Si](C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C	3020.9	Standard non polar	33892256
Laurolitsine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(OC)C(O)=C3	3226.8	Semi standard non polar	33892256
Laurolitsine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)CC1NCCC3=C1C2=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3	3213.9	Semi standard non polar	33892256
Laurolitsine,1TBDMS,isomer #3	COC1=CC2=C(C=C1O)CC1C3=C(C=C(O)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3147.1	Semi standard non polar	33892256
Laurolitsine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3	3294.3	Semi standard non polar	33892256
Laurolitsine,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(O)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3275.6	Semi standard non polar	33892256
Laurolitsine,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)CC1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3286.8	Semi standard non polar	33892256
Laurolitsine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3443.2	Semi standard non polar	33892256
Laurolitsine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C	3663.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Laurolitsine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l2-0090000000-e696484cc73c01660196	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laurolitsine GC-MS (2 TMS) - 70eV, Positive	splash10-01ox-2017900000-7c77965a1ca1bd0381c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laurolitsine 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 - Laurolitsine 10V, Positive-QTOF	splash10-03di-0019000000-d651cc4e4cb5afa0d8fe	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 20V, Positive-QTOF	splash10-03di-0096000000-feec91fd2946722b0e8b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 40V, Positive-QTOF	splash10-00g4-0290000000-8bf70db071205af68fb2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 10V, Negative-QTOF	splash10-03di-0009000000-df332e9a25f01395050d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 20V, Negative-QTOF	splash10-03di-0069000000-cf2fb1b164ef6cd4df06	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 40V, Negative-QTOF	splash10-0gba-0090000000-a40c8736b6b1df93772f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 10V, Positive-QTOF	splash10-03di-0009000000-7a1d998903fa1bad0b1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 20V, Positive-QTOF	splash10-03di-0029000000-0ecb1d8faf62679fd231	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 40V, Positive-QTOF	splash10-002f-0191000000-e53640d951b4a6c17995	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 10V, Negative-QTOF	splash10-03di-0009000000-5cd9c8e6e0b2900b51af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 20V, Negative-QTOF	splash10-03di-0029000000-edd2faa7fc1a5379984e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurolitsine 40V, Negative-QTOF	splash10-03dl-0094000000-f10756d1af590b075205	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628557

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 Laurolitsine (HMDB0040974)

MOL for HMDB0040974 (Laurolitsine)

3D MOL for HMDB0040974 (Laurolitsine)

3D SDF for HMDB0040974 (Laurolitsine)

3D-SDF for HMDB0040974 (Laurolitsine)

PDB for HMDB0040974 (Laurolitsine)

3D PDB for HMDB0040974 (Laurolitsine)

SMILES for HMDB0040974 (Laurolitsine)

INCHI for HMDB0040974 (Laurolitsine)

Structure for HMDB0040974 (Laurolitsine)

3D Structure for HMDB0040974 (Laurolitsine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra