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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:28 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030211

Secondary Accession Numbers

HMDB30211

Metabolite Identification

Common Name

(R)-Laudanidine

Description

(R)-Laudanidine, also known as tritopin or DL-laudanine, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-Laudanidine has been detected, but not quantified in, opium poppies (Papaver somniferum). This could make (R)-laudanidine a potential biomarker for the consumption of these foods (R)-Laudanidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (R)-Laudanidine.

Structure

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

HMDB0030211
     RDKit          3D
(R)-Laudanidine
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1735    0.4810    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -0.0494   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9458    0.1740   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425    0.9878    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.1446    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698    0.5260   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7000   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -0.3556    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.2795   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    0.4860   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5034    0.5207   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    1.3019   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944    2.0656   -2.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.2533   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -0.1812   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5236   -0.8558    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.0272    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -1.0415    0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.9030    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -1.6558    1.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -0.4010    1.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    0.7426    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772   -0.2860   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -0.4495   -1.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102   -1.2735   -2.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.7311    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9814   -0.2855    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.3789    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990    1.4671    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.7866    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    1.7226   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582    0.5159   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.3504   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092    1.0747   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    2.6539   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    2.7404   -3.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    1.3785   -3.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4228   -0.2277    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1421   -1.2117    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8982   -1.7474    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1430   -1.6159    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -1.6651    2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397   -2.9587    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275   -1.7355    3.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -2.4592    1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.6643    2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    1.6403    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    0.9095    3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7790   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.7454   -2.9321 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  8  1  0
 18  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 25 50  1  0
M  END


  Mrv0541 05061305052D          

 25 27  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
    0.7145   -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
    0.7145   -3.7125    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18  6  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 19  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
 25  4  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030211

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3

> <INCHI_KEY>
MPYHGNAJOKCMAQ-UHFFFAOYSA-N

> <FORMULA>
C20H25NO4

> <MOLECULAR_WEIGHT>
343.4168

> <EXACT_MASS>
343.178358293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.92369923340091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.1337083402344486

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.018452217949251

> <JCHEM_PKA_STRONGEST_BASIC>
8.272279750978452

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
98.31859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
laudanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030211
     RDKit          3D
(R)-Laudanidine
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1735    0.4810    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -0.0494   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9458    0.1740   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425    0.9878    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.1446    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698    0.5260   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7000   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -0.3556    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.2795   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    0.4860   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5034    0.5207   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    1.3019   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944    2.0656   -2.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.2533   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -0.1812   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5236   -0.8558    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.0272    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -1.0415    0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.9030    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -1.6558    1.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -0.4010    1.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    0.7426    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772   -0.2860   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -0.4495   -1.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102   -1.2735   -2.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.7311    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9814   -0.2855    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.3789    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990    1.4671    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.7866    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    1.7226   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582    0.5159   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.3504   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092    1.0747   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    2.6539   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    2.7404   -3.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    1.3785   -3.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4228   -0.2277    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1421   -1.2117    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8982   -1.7474    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1430   -1.6159    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -1.6651    2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397   -2.9587    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275   -1.7355    3.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -2.4592    1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.6643    2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    1.6403    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    0.9095    3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7790   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.7454   -2.9321 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  8  1  0
 18  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 25 50  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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -9.240   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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6   13                                                       
CONECT    6    5   18                                                       
CONECT    7    8   14                                                       
CONECT    8    7   21                                                       
CONECT    9   13   16                                                       
CONECT   10   13   17                                                       
CONECT   11   14   19                                                       
CONECT   12   15   20                                                       
CONECT   13    5    9   10                                                  
CONECT   14    7   11   15                                                  
CONECT   15   12   14   16                                                  
CONECT   16    9   15   21                                                  
CONECT   17   10   18   22                                                  
CONECT   18    6   17   23                                                  
CONECT   19   11   20   24                                                  
CONECT   20   12   19   25                                                  
CONECT   21    1    8   16                                                  
CONECT   22   17                                                            
CONECT   23    2   18                                                       
CONECT   24    3   19                                                       
CONECT   25    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0030211
HETATM    1  C1  UNL     1       7.174   0.481   0.738  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.292  -0.049  -0.201  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.946   0.174  -0.280  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.243   0.988   0.591  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.881   1.145   0.420  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.170   0.526  -0.587  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.704   0.700  -0.764  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.015  -0.356   0.028  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.469  -0.279  -0.075  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.126   0.486  -0.988  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.503   0.521  -1.041  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.171   1.302  -1.972  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.394   2.066  -2.871  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.233  -0.253  -0.129  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.606  -0.181  -0.226  1.00  0.00           O  
HETATM   16  C13 UNL     1      -6.524  -0.856   0.566  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.571  -1.027   0.794  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.189  -1.042   0.823  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.552  -1.903   1.850  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.076  -1.656   1.980  1.00  0.00           C  
HETATM   21  N1  UNL     1       0.358  -0.401   1.414  1.00  0.00           N  
HETATM   22  C18 UNL     1      -0.196   0.743   2.097  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.877  -0.286  -1.455  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.242  -0.449  -1.292  1.00  0.00           C  
HETATM   25  O4  UNL     1       4.910  -1.273  -2.186  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.674   0.731   1.696  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.981  -0.286   0.925  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.720   1.379   0.344  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.799   1.467   1.373  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.363   1.787   1.118  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.393   1.723  -0.537  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.458   0.516  -1.843  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.289  -1.350  -0.433  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.509   1.075  -1.680  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.611   2.654  -2.354  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.003   2.740  -3.494  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.874   1.378  -3.600  1.00  0.00           H  
HETATM   38  H13 UNL     1      -7.423  -0.228   0.795  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.142  -1.212   1.527  1.00  0.00           H  
HETATM   40  H15 UNL     1      -6.898  -1.747   0.000  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.143  -1.616   1.487  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.017  -1.665   2.850  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.740  -2.959   1.574  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.228  -1.736   3.047  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.453  -2.459   1.413  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.258   0.664   2.335  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.077   1.640   1.444  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.354   0.910   3.067  1.00  0.00           H  
HETATM   49  H24 UNL     1       2.335  -0.779  -2.250  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.448  -1.745  -2.932  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   23
CONECT    7    8   31   32
CONECT    8    9   21   33
CONECT    9   10   10   18
CONECT   10   11   34
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   35   36   37
CONECT   14   15   17
CONECT   15   16
CONECT   16   38   39   40
CONECT   17   18   18   41
CONECT   18   19
CONECT   19   20   42   43
CONECT   20   21   44   45
CONECT   21   22
CONECT   22   46   47   48
CONECT   23   24   24   49
CONECT   24   25
CONECT   25   50
END

HMDB0030211
     RDKit          3D
(R)-Laudanidine
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1735    0.4810    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -0.0494   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9458    0.1740   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425    0.9878    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.1446    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698    0.5260   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7000   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -0.3556    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.2795   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    0.4860   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5034    0.5207   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    1.3019   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944    2.0656   -2.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.2533   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -0.1812   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5236   -0.8558    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.0272    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -1.0415    0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.9030    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -1.6558    1.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -0.4010    1.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    0.7426    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772   -0.2860   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -0.4495   -1.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102   -1.2735   -2.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.7311    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9814   -0.2855    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.3789    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990    1.4671    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.7866    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    1.7226   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582    0.5159   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.3504   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092    1.0747   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    2.6539   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    2.7404   -3.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    1.3785   -3.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4228   -0.2277    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1421   -1.2117    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8982   -1.7474    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1430   -1.6159    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -1.6651    2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397   -2.9587    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275   -1.7355    3.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -2.4592    1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.6643    2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    1.6403    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    0.9095    3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7790   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.7454   -2.9321 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  8  1  0
 18  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 25 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Laudanidine	HMDB
DL-Laudanine	HMDB
Tritopin	HMDB
Tritopine	HMDB

Chemical Formula

C₂₀H₂₅NO₄

Average Molecular Weight

343.4168

Monoisotopic Molecular Weight

343.178358293

IUPAC Name

5-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol

Traditional Name

laudanine

CAS Registry Number

301-21-3

SMILES

COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1

InChI Identifier

InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3

InChI Key

MPYHGNAJOKCMAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:76103 )
phenols (CHEBI:76103 )
benzylisoquinoline alkaloid (CHEBI:76103 )
benzyltetrahydroisoquinoline (CHEBI:76103 )
Isoquinoline alkaloids (C17592 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030211)

Opium poppy (FooDB: FOOD00438)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	184 - 185 °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	3.19	ALOGPS
logP	3.13	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.02	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	37.92 Å³	ChemAxon
Number of Rings	3	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]+	183.587	31661259
DarkChem	[M-H]-	184.603	31661259
DeepCCS	[M-2H]-	219.267	30932474
DeepCCS	[M+Na]+	195.286	30932474
AllCCS	[M+H]+	184.8	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.7	32859911
AllCCS	[M+Na]+	188.5	32859911
AllCCS	[M-H]-	189.6	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Laudanidine	COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1	4076.2	Standard polar	33892256
(R)-Laudanidine	COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1	2772.0	Standard non polar	33892256
(R)-Laudanidine	COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1	2769.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Laudanidine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C(CC1=CC=C(OC)C(O[Si](C)(C)C)=C1)N(C)CC2	2740.3	Semi standard non polar	33892256
(R)-Laudanidine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C(CC1=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC2	2959.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Laudanidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-1981000000-cc68b102f172fbb3ade9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Laudanidine GC-MS (1 TMS) - 70eV, Positive	splash10-0r6r-2950200000-906a1df54edede6d4608	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Laudanidine 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 - (R)-Laudanidine 10V, Positive-QTOF	splash10-0006-0009000000-2a2a7726cd989268ed12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 20V, Positive-QTOF	splash10-0btc-0679000000-b728082320290c20a63b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 40V, Positive-QTOF	splash10-00fr-1930000000-b96edd90b8e3a35f2fe0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 10V, Negative-QTOF	splash10-0006-0009000000-e51949b59b42fd623188	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 20V, Negative-QTOF	splash10-002f-0019000000-31ff5cd819e6d3c3fed9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 40V, Negative-QTOF	splash10-006t-0092000000-e09e7fc4b625837e1bed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 10V, Positive-QTOF	splash10-0006-0009000000-4684e4ff69877ecc7651	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 20V, Positive-QTOF	splash10-0a4l-0395000000-b3225b24861eb85964c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 40V, Positive-QTOF	splash10-002f-0932000000-3773eccbac0b02e2fe30	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 10V, Negative-QTOF	splash10-0006-0009000000-5a516184c230fa2e7a58	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 20V, Negative-QTOF	splash10-0006-0029000000-f9df69fb6470379eaf18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Laudanidine 40V, Negative-QTOF	splash10-0007-0393000000-f28f42c4f79e561f0730	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

92732

PDB ID

Not Available

ChEBI ID

76103

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 (R)-Laudanidine (HMDB0030211)

MOL for HMDB0030211 ((R)-Laudanidine)

3D MOL for HMDB0030211 ((R)-Laudanidine)

3D SDF for HMDB0030211 ((R)-Laudanidine)

3D-SDF for HMDB0030211 ((R)-Laudanidine)

PDB for HMDB0030211 ((R)-Laudanidine)

3D PDB for HMDB0030211 ((R)-Laudanidine)

SMILES for HMDB0030211 ((R)-Laudanidine)

INCHI for HMDB0030211 ((R)-Laudanidine)

Structure for HMDB0030211 ((R)-Laudanidine)

3D Structure for HMDB0030211 ((R)-Laudanidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra