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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:34:05 UTC

Update Date

2022-11-23 22:29:17 UTC

HMDB ID

HMDB0255751

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Norscopolamine

Description

3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Norscopolamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Norscopolamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255751
     RDKit          3D
norscopolamine
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.2999   -2.6893   -0.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8021   -1.5233   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603   -0.4677   -0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6663   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.0696   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.2858   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.3147    0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -0.5552    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -0.0638    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105    0.6762    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3221    0.5010    1.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736    0.9143    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -1.3431   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -0.6494   -2.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089    0.6050   -2.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -0.5934   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    0.6614    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.4077    1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5312    0.8267    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -0.4323    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729   -1.1352    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.7550   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145   -0.6615   -2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719    0.9835   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.6356   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.5286    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.0895    2.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    1.0362    1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.3151    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    1.3979    2.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.8739   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -2.3608   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137   -1.2695   -3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734   -0.4783   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9315    0.6440   -3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442    1.0736   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    2.3925    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    1.3953    2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395   -0.8329    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340   -2.1371    0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 12 10  1  0
 21 16  1  0
 12  6  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv1533004161515372D          

 21 24  0  0  0  0            999 V2000
    7.1883    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3633    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508    0.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258    0.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943    0.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260   -0.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3666    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3633   -0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6008   -1.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -1.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3633   -1.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -1.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 15  1  0  0  0  0
  3 16  1  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
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255751

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC(C(=O)OC1CC2NC(C1)C1OC21)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO4/c18-8-11(9-4-2-1-3-5-9)16(19)20-10-6-12-14-15(21-14)13(7-10)17-12/h1-5,10-15,17-18H,6-8H2

> <INCHI_KEY>
MOYZEMOPQDTDHA-UHFFFAOYSA-N

> <FORMULA>
C16H19NO4

> <MOLECULAR_WEIGHT>
289.331

> <EXACT_MASS>
289.131408096

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.10462892523651

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.5119043576666664

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145740069953202

> <JCHEM_PKA_STRONGEST_BASIC>
8.823690298926604

> <JCHEM_POLAR_SURFACE_AREA>
71.09

> <JCHEM_REFRACTIVITY>
74.42660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255751
     RDKit          3D
norscopolamine
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.2999   -2.6893   -0.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8021   -1.5233   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603   -0.4677   -0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6663   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.0696   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.2858   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.3147    0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -0.5552    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -0.0638    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105    0.6762    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3221    0.5010    1.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736    0.9143    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -1.3431   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -0.6494   -2.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089    0.6050   -2.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -0.5934   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    0.6614    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.4077    1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5312    0.8267    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -0.4323    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729   -1.1352    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.7550   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145   -0.6615   -2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719    0.9835   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.6356   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.5286    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.0895    2.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    1.0362    1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.3151    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    1.3979    2.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.8739   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -2.3608   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137   -1.2695   -3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734   -0.4783   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9315    0.6440   -3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442    1.0736   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    2.3925    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    1.3953    2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395   -0.8329    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340   -2.1371    0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 12 10  1  0
 21 16  1  0
 12  6  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      13.418   1.657   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.878   1.657   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.108   0.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.568   0.323   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.798  -1.011   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.798   1.657   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.258   1.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.590   3.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.089   3.387   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.656   1.657   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.089  -0.074   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.590   0.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.885   0.887   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.551   1.657   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.885   2.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.878  -1.011   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.418  -1.011   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.188  -2.344   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.418  -3.678   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.878  -3.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.108  -2.344   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   13                                                  
CONECT   16    3   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0255751
HETATM    1  O1  UNL     1       0.300  -2.689  -0.574  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.802  -1.523  -0.729  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.060  -0.468  -0.507  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.385  -0.666  -0.140  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.382  -0.070  -1.116  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.758  -0.286  -0.543  1.00  0.00           C  
HETATM    7  N1  UNL     1      -3.716  -1.315   0.508  1.00  0.00           N  
HETATM    8  C5  UNL     1      -3.096  -0.555   1.598  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.718  -0.064   1.219  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.011   0.676   1.600  1.00  0.00           C  
HETATM   11  O3  UNL     1      -5.322   0.501   1.139  1.00  0.00           O  
HETATM   12  C8  UNL     1      -4.274   0.914   0.214  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.222  -1.343  -1.121  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.314  -0.649  -2.488  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.709   0.605  -2.456  1.00  0.00           O  
HETATM   16  C11 UNL     1       3.021  -0.593  -0.156  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.649   0.661   0.247  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.375   1.408   1.157  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.531   0.827   1.667  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.937  -0.432   1.285  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.173  -1.135   0.371  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.657  -1.755  -0.050  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.314  -0.662  -2.055  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.172   0.984  -1.350  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.482  -0.636  -1.299  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.682  -1.529   0.780  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.116  -1.090   2.549  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.675   1.036   1.081  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.952  -0.315   1.974  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.928   1.398   2.409  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.420   1.874  -0.275  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.650  -2.361  -1.313  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.814  -1.269  -3.268  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.373  -0.478  -2.765  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.932   0.644  -3.085  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.744   1.074  -0.173  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.088   2.392   1.477  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.112   1.395   2.380  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.839  -0.833   1.711  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.534  -2.137   0.095  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4
CONECT    4    5    9   22
CONECT    5    6   23   24
CONECT    6    7   12   25
CONECT    7    8   26
CONECT    8    9   10   27
CONECT    9   28   29
CONECT   10   11   12   30
CONECT   11   12
CONECT   12   31
CONECT   13   14   16   32
CONECT   14   15   33   34
CONECT   15   35
CONECT   16   17   17   21
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21   39
CONECT   21   40
END

HMDB0255751
     RDKit          3D
norscopolamine
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.2999   -2.6893   -0.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8021   -1.5233   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603   -0.4677   -0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6663   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.0696   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.2858   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.3147    0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -0.5552    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -0.0638    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105    0.6762    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3221    0.5010    1.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736    0.9143    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -1.3431   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -0.6494   -2.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089    0.6050   -2.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -0.5934   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    0.6614    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.4077    1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5312    0.8267    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -0.4323    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729   -1.1352    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.7550   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145   -0.6615   -2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719    0.9835   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.6356   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.5286    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.0895    2.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    1.0362    1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.3151    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    1.3979    2.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.8739   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -2.3608   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137   -1.2695   -3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734   -0.4783   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9315    0.6440   -3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442    1.0736   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    2.3925    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    1.3953    2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395   -0.8329    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340   -2.1371    0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 12 10  1  0
 21 16  1  0
 12  6  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Oxa-9-azatricyclo[3.3.1.0,]nonan-7-yl 3-hydroxy-2-phenylpropanoic acid	Generator

Chemical Formula

C₁₆H₁₉NO₄

Average Molecular Weight

289.331

Monoisotopic Molecular Weight

289.131408096

IUPAC Name

3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

Traditional Name

3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

CAS Registry Number

Not Available

SMILES

OCC(C(=O)OC1CC2NC(C1)C1OC21)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H19NO4/c18-8-11(9-4-2-1-3-5-9)16(19)20-10-6-12-14-15(21-14)13(7-10)17-12/h1-5,10-15,17-18H,6-8H2

InChI Key

MOYZEMOPQDTDHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocyclic benzene moiety
Morpholine
Oxazinane
Piperidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	0.35	ALOGPS
logP	0.51	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.43 m³·mol⁻¹	ChemAxon
Polarizability	29.1 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
DeepCCS	[M-2H]-	196.153	30932474
DeepCCS	[M+Na]+	171.718	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
norscopolamine	OCC(C(=O)OC1CC2NC(C1)C1OC21)C1=CC=CC=C1	3324.2	Standard polar	33892256
norscopolamine	OCC(C(=O)OC1CC2NC(C1)C1OC21)C1=CC=CC=C1	2323.4	Standard non polar	33892256
norscopolamine	OCC(C(=O)OC1CC2NC(C1)C1OC21)C1=CC=CC=C1	2429.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
norscopolamine,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C)C1=CC=CC=C1	2418.6	Semi standard non polar	33892256
norscopolamine,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C)C1=CC=CC=C1	2521.9	Standard non polar	33892256
norscopolamine,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C)C1=CC=CC=C1	3104.7	Standard polar	33892256
norscopolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2848.8	Semi standard non polar	33892256
norscopolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2936.3	Standard non polar	33892256
norscopolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)OC1CC2C3OC3C(C1)N2[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3285.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9820000000-fbea8058678837850381	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norscopolamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10424253

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Norscopolamine (HMDB0255751)

MOL for HMDB0255751 (Norscopolamine)

3D MOL for HMDB0255751 (Norscopolamine)

3D SDF for HMDB0255751 (Norscopolamine)

3D-SDF for HMDB0255751 (Norscopolamine)

PDB for HMDB0255751 (Norscopolamine)

3D PDB for HMDB0255751 (Norscopolamine)

SMILES for HMDB0255751 (Norscopolamine)

INCHI for HMDB0255751 (Norscopolamine)

Structure for HMDB0255751 (Norscopolamine)

3D Structure for HMDB0255751 (Norscopolamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra