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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:30 UTC

Update Date

2021-09-14 15:47:52 UTC

HMDB ID

HMDB0012486

Secondary Accession Numbers

HMDB12486

Metabolite Identification

Common Name

Norlaudanosoline

Description

Norlaudanosoline (CAS: 4747-99-3), also known as tetrahydropapaveroline, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Norlaudanosoline is a very strong basic compound (based on its pKa). Norlaundanosoline is a key intermediate in the synthesis of the benzylisoquinoline alkaloids, providing the upper isoquinoline portion of the morphinan skeleton. It is involved in alkaloid biosynthesis and is synthesized by the enzyme (S)-norlaudanosoline synthase.

Structure

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

HMDB0012486
     RDKit          3D
Norlaudanosoline
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.0439   -0.8347    0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -0.6264    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.6487   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395   -1.4336   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.1630   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.1176   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -0.0484    0.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -1.4026    1.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893   -2.2391    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.9114    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594   -0.5185    0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369   -0.1034    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.1893   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    1.6111   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756    2.0736   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3368    3.3923   -0.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    1.6278   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    0.3448    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603    0.8511    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    0.6340    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    1.7060    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -0.0752    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -2.6605   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -2.2490   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    1.1865   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -0.5785   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    0.6096    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.5195    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7724   -3.3315    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -1.9392   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -2.6338    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -1.8939    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8025   -0.7624    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355    2.5542   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1911    3.8581   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    2.3181   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.8694    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    2.6295    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 21 38  1  0
M  END


  Mrv1652303062020272D          

 21 23  0  0  0  0            999 V2000
10000.0213 9999.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.451710002.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.876910001.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1730 9999.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1730 9997.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5983 9999.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8837 9998.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8837 9997.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5982 9997.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0223 9999.1622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3078 9998.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3078 9997.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0223 9997.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7368 9997.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7368 9998.7497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.164110001.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.449710001.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.735110001.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.735110000.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4496 9999.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.164110000.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8  5  1  0  0  0  0
  7  4  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 14 15  1  0  0  0  0
 10  1  1  6  0  0  0
 11  6  2  0  0  0  0
  9 12  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
  1 19  1  0  0  0  0
 17  2  1  0  0  0  0
 16  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012486

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(O)C=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c18-13-2-1-9(6-14(13)19)5-12-11-8-16(21)15(20)7-10(11)3-4-17-12/h1-2,6-8,12,17-21H,3-5H2/t12-/m0/s1

> <INCHI_KEY>
ABXZOXDTHTTZJW-LBPRGKRZSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.11355278556588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.9558963615535554

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.825426041903222

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.479914583644334

> <JCHEM_PKA_STRONGEST_BASIC>
9.240357178873596

> <JCHEM_POLAR_SURFACE_AREA>
92.95

> <JCHEM_REFRACTIVITY>
79.57700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-norlaudanosoline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012486
     RDKit          3D
Norlaudanosoline
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.0439   -0.8347    0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -0.6264    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.6487   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395   -1.4336   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.1630   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.1176   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -0.0484    0.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -1.4026    1.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893   -2.2391    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.9114    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594   -0.5185    0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369   -0.1034    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.1893   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    1.6111   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756    2.0736   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3368    3.3923   -0.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    1.6278   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    0.3448    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603    0.8511    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    0.6340    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    1.7060    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -0.0752    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -2.6605   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -2.2490   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    1.1865   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -0.5785   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    0.6096    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.5195    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7724   -3.3315    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -1.9392   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -2.6338    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -1.8939    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8025   -0.7624    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355    2.5542   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1911    3.8581   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    2.3181   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.8694    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    2.6295    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8666.7068666.651   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.3778671.264   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8672.0378669.726   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8661.3908665.109   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.3908662.021   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8664.0508665.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.7168664.333   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7168662.793   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.0508662.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.7088665.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3758664.333   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3758662.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7088662.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0428662.793   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8668.0428664.333   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8670.7068668.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.3738669.731   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.0398668.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0398667.421   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3738666.651   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.7068667.421   0.000  0.00  0.00           C+0
CONECT    1   10   19                                                       
CONECT    2   17                                                            
CONECT    3   16                                                            
CONECT    4    7                                                            
CONECT    5    8                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   12                                                       
CONECT   10   11   15    1                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13    9                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   17   21    3                                                  
CONECT   17   16   18    2                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20    1                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0012486
HETATM    1  O1  UNL     1       6.044  -0.835   0.568  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.703  -0.626   0.251  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.879  -1.649  -0.162  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.540  -1.434  -0.478  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.041  -0.163  -0.370  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.635   0.118  -0.691  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.193  -0.048   0.571  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.037  -1.403   1.024  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.989  -2.239   0.346  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.373  -1.911   0.919  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.659  -0.518   0.508  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.937  -0.103   0.293  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.220   1.189  -0.091  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.515   1.611  -0.310  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.176   2.074  -0.256  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.337   3.392  -0.636  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.874   1.628  -0.029  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.604   0.345   0.350  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.860   0.851   0.040  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.194   0.634   0.354  1.00  0.00           C  
HETATM   21  O4  UNL     1       4.997   1.706   0.770  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.635  -0.075   0.869  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.276  -2.661  -0.248  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.897  -2.249  -0.803  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.517   1.187  -1.029  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.293  -0.578  -1.482  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.261   0.610   1.367  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.014  -1.519   2.046  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.772  -3.331   0.459  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.017  -1.939  -0.718  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.131  -2.634   0.616  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.229  -1.894   2.029  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.802  -0.762   0.409  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.736   2.554  -0.590  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.191   3.858  -0.833  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.059   2.318  -0.158  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.506   1.869   0.138  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.588   2.630   0.836  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3   20
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   19
CONECT    6    7   25   26
CONECT    7    8   18   27
CONECT    8    9   28
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   12   18
CONECT   12   13   33
CONECT   13   14   15   15
CONECT   14   34
CONECT   15   16   17
CONECT   16   35
CONECT   17   18   18   36
CONECT   19   20   20   37
CONECT   20   21
CONECT   21   38
END

HMDB0012486
     RDKit          3D
Norlaudanosoline
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.0439   -0.8347    0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -0.6264    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.6487   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395   -1.4336   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.1630   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.1176   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -0.0484    0.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -1.4026    1.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893   -2.2391    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.9114    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594   -0.5185    0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369   -0.1034    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.1893   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    1.6111   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756    2.0736   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3368    3.3923   -0.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    1.6278   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    0.3448    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603    0.8511    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    0.6340    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    1.7060    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -0.0752    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -2.6605   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -2.2490   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    1.1865   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -0.5785   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    0.6096    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.5195    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7724   -3.3315    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -1.9392   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -2.6338    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -1.8939    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8025   -0.7624    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355    2.5542   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1911    3.8581   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    2.3181   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.8694    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    2.6295    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-Tetrahydropapaveroline	ChEBI
(-)-Tetrahydropapaveroline	HMDB
(1S)-1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-isoquinolinediol	HMDB
(S)-(-)-Tetrahydropapaveroline	HMDB
(S)-Norlaudanosoline	HMDB
1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-isoquinolinediol	HMDB
Tetrahydropapaveroline	HMDB
Norlaudanosoline	HMDB

Chemical Formula

C₁₆H₁₇NO₄

Average Molecular Weight

287.315

Monoisotopic Molecular Weight

287.115758031

IUPAC Name

(1S)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

(S)-norlaudanosoline

CAS Registry Number

57073-15-1

SMILES

OC1=C(O)C=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C23)C=C1

InChI Identifier

InChI=1S/C16H17NO4/c18-13-2-1-9(6-14(13)19)5-12-11-8-16(21)15(20)7-10(11)3-4-17-12/h1-2,6-8,12,17-21H,3-5H2/t12-/m0/s1

InChI Key

ABXZOXDTHTTZJW-LBPRGKRZSA-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
Tetrahydroisoquinoline
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Secondary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

norlaudanosoline (CHEBI:28651 )
Isoquinoline alkaloids (C02916 )

Ontology

Not Available

Endogenous (HMDB: HMDB0012486)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.32 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.96	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	92.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.58 m³·mol⁻¹	ChemAxon
Polarizability	30.11 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
DeepCCS	[M-2H]-	205.627	30932474
DeepCCS	[M+Na]+	181.262	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	172.1	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	170.1	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norlaudanosoline	OC1=C(O)C=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C23)C=C1	3835.8	Standard polar	33892256
Norlaudanosoline	OC1=C(O)C=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C23)C=C1	3065.3	Standard non polar	33892256
Norlaudanosoline	OC1=C(O)C=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C23)C=C1	3156.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norlaudanosoline,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)C=C1O	2966.5	Semi standard non polar	33892256
Norlaudanosoline,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)=CC=C1O	2957.6	Semi standard non polar	33892256
Norlaudanosoline,1TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O)=C1)NCC2	2959.6	Semi standard non polar	33892256
Norlaudanosoline,1TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN[C@H]2CC1=CC=C(O)C(O)=C1	2951.8	Semi standard non polar	33892256
Norlaudanosoline,1TMS,isomer #5	C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2[C@@H]1CC1=CC=C(O)C(O)=C1	3040.9	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C)=C(O)C=C32)C=C1O	2823.6	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #10	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)[C@H]2CC1=CC=C(O)C(O)=C1	2895.7	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O[Si](C)(C)C)C=C32)C=C1O	2826.3	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)C=C1O[Si](C)(C)C	2869.5	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C)C=C1O	2900.6	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O[Si](C)(C)C)=C(O)C=C32)=CC=C1O	2814.7	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #6	C[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O)=C(O[Si](C)(C)C)C=C32)=CC=C1O	2816.2	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #7	C[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C)=CC=C1O	2921.0	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #8	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)NCC2	2876.7	Semi standard non polar	33892256
Norlaudanosoline,2TMS,isomer #9	C[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C)CC2	2911.8	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C32)C=C1O	2868.8	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #10	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C)CC2	2834.6	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)NCC2	2855.9	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1O	2856.9	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN[C@H]2CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2865.8	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C)C=C1O	2839.8	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C)C=C1O[Si](C)(C)C	2879.2	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #7	C[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C32)=CC=C1O	2853.0	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #8	C[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)=CC=C1O	2847.1	Semi standard non polar	33892256
Norlaudanosoline,3TMS,isomer #9	C[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C)=CC=C1O	2829.9	Semi standard non polar	33892256
Norlaudanosoline,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C32)C=C1O[Si](C)(C)C	2929.8	Semi standard non polar	33892256
Norlaudanosoline,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1O	2897.5	Semi standard non polar	33892256
Norlaudanosoline,4TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)CC2	2910.3	Semi standard non polar	33892256
Norlaudanosoline,4TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)[C@H]2CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2902.0	Semi standard non polar	33892256
Norlaudanosoline,4TMS,isomer #5	C[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)=CC=C1O	2879.5	Semi standard non polar	33892256
Norlaudanosoline,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1O[Si](C)(C)C	2972.9	Semi standard non polar	33892256
Norlaudanosoline,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1O[Si](C)(C)C	2911.0	Standard non polar	33892256
Norlaudanosoline,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1O[Si](C)(C)C	2949.9	Standard polar	33892256
Norlaudanosoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)C=C1O	3267.1	Semi standard non polar	33892256
Norlaudanosoline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)=CC=C1O	3239.8	Semi standard non polar	33892256
Norlaudanosoline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O)=C1)NCC2	3266.1	Semi standard non polar	33892256
Norlaudanosoline,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN[C@H]2CC1=CC=C(O)C(O)=C1	3248.8	Semi standard non polar	33892256
Norlaudanosoline,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2[C@@H]1CC1=CC=C(O)C(O)=C1	3313.0	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C32)C=C1O	3380.9	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)[C@H]2CC1=CC=C(O)C(O)=C1	3430.0	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C1O	3377.1	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O)=C(O)C=C32)C=C1O[Si](C)(C)C(C)(C)C	3404.9	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O	3435.7	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C32)=CC=C1O	3354.1	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C32)=CC=C1O	3353.7	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)=CC=C1O	3444.5	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)NCC2	3398.9	Semi standard non polar	33892256
Norlaudanosoline,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)CC2	3437.8	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C1O	3568.0	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)CC2	3599.1	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)NCC2	3556.4	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O	3613.5	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN[C@H]2CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3548.7	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O	3608.3	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3617.3	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H]2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C32)=CC=C1O	3544.7	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)=CC=C1O	3602.1	Semi standard non polar	33892256
Norlaudanosoline,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)=CC=C1O	3598.8	Semi standard non polar	33892256
Norlaudanosoline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H]2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C1O[Si](C)(C)C(C)(C)C	3748.0	Semi standard non polar	33892256
Norlaudanosoline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O	3815.6	Semi standard non polar	33892256
Norlaudanosoline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)CC2	3806.3	Semi standard non polar	33892256
Norlaudanosoline,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)[C@H]2CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3801.5	Semi standard non polar	33892256
Norlaudanosoline,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)=CC=C1O	3793.8	Semi standard non polar	33892256
Norlaudanosoline,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4002.3	Semi standard non polar	33892256
Norlaudanosoline,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3812.0	Standard non polar	33892256
Norlaudanosoline,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3387.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norlaudanosoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-QTOF , positive-QTOF	splash10-000i-0190000000-ebe0bcf51deee4d03416	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-QTOF , positive-QTOF	splash10-03k9-0890000000-454a3dba17fb0a9a1feb	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-QTOF , positive-QTOF	splash10-03k9-0930000000-eb86d1f7598002b19864	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-QTOF , positive-QTOF	splash10-03k9-0920000000-0fea3d6de92f4642847e	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-ITFT , positive-QTOF	splash10-03k9-0940000000-e50e320f378c9740d3f8	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-ITFT , positive-QTOF	splash10-03k9-0940000000-6d5f7447c6ff2d55f82e	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-ITFT , positive-QTOF	splash10-03k9-0940000000-0d5683453b5fd9dfcc67	2020-03-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norlaudanosoline LC-ESI-ITFT , positive-QTOF	splash10-03k9-0940000000-e2203c1ceb15a4ff4500	2020-03-03	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 10V, Negative-QTOF	splash10-000i-0090000000-c754a389ec3f588c9a88	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 20V, Negative-QTOF	splash10-000i-0290000000-703a2b5e7b475c04bbb4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 40V, Negative-QTOF	splash10-004i-1930000000-aafe5d881040d6d681ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 10V, Positive-QTOF	splash10-000i-0090000000-7df6ac01694af44ff067	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 20V, Positive-QTOF	splash10-000i-0490000000-9751ff9ed965a11e957a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norlaudanosoline 40V, Positive-QTOF	splash10-0ly9-1940000000-de8c7d883fecad3d3c8b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Tetrahydropapaveroline

METLIN ID

Not Available

PubChem Compound

439845

PDB ID

Not Available

ChEBI ID

28651

Food Biomarker Ontology

Not Available

VMH ID

C06350

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Norlaudanosoline (HMDB0012486)

MOL for HMDB0012486 (Norlaudanosoline)

3D MOL for HMDB0012486 (Norlaudanosoline)

3D SDF for HMDB0012486 (Norlaudanosoline)

3D-SDF for HMDB0012486 (Norlaudanosoline)

PDB for HMDB0012486 (Norlaudanosoline)

3D PDB for HMDB0012486 (Norlaudanosoline)

SMILES for HMDB0012486 (Norlaudanosoline)

INCHI for HMDB0012486 (Norlaudanosoline)

Structure for HMDB0012486 (Norlaudanosoline)

3D Structure for HMDB0012486 (Norlaudanosoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra