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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:54:31 UTC

Update Date

2022-03-07 02:55:50 UTC

HMDB ID

HMDB0038584

Secondary Accession Numbers

HMDB38584

Metabolite Identification

Common Name

Piperolactam C

Description

Piperolactam C belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system. Piperolactam C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, piperolactam C has been detected, but not quantified in, herbs and spices. This could make piperolactam C a potential biomarker for the consumption of these foods.

Structure

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

HMDB0038584
     RDKit          3D
Piperolactam C
 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.8670   -1.7013   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2812   -1.4323    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.9203    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7406    0.4255    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527    1.3353    0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    1.8933    1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063    0.9019    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238    2.2523    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579    2.9800   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037   -0.0024    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -1.3793    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191   -2.3548    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -1.9928    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8865   -0.6346    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.2914    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940    1.0246    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327    1.9940    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    1.6952    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.3741    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4913   -3.5903    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -3.3149    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -4.1275    0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745   -1.8522    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207   -1.1602   -2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -1.3370   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -2.7615   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    1.4420    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.7775    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2003    2.9873    1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4244   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2437    2.9352   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    3.9962   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -2.7473    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.0969    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6563    1.2504    0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    3.0139    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    2.5138    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -4.5200    0.2444 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  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  3  1  0
 19 10  1  0
 23 11  2  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
M  END


  Mrv0541 02241209182D          

 23 26  0  0  0  0            999 V2000
    0.3255   -2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -0.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3976   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -0.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976    1.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976    1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    2.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    1.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3976    0.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    0.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425    1.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670    2.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738    0.7235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493    0.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -0.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4255   -0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9044   -1.4479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  2  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5 23  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038584

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C(OC)=C2C3=C1C(=O)NC3=CC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO4/c1-21-15-12-10-7-5-4-6-9(10)8-11-13(12)14(18(20)19-11)16(22-2)17(15)23-3/h4-8H,1-3H3,(H,19,20)

> <INCHI_KEY>
GYYIMUXZCUHECT-UHFFFAOYSA-N

> <FORMULA>
C18H15NO4

> <MOLECULAR_WEIGHT>
309.316

> <EXACT_MASS>
309.100107973

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.263699360913904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.597824522

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.800751148708526

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11999293864838

> <JCHEM_POLAR_SURFACE_AREA>
56.790000000000006

> <JCHEM_REFRACTIVITY>
87.82350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038584
     RDKit          3D
Piperolactam C
 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.8670   -1.7013   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2812   -1.4323    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.9203    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7406    0.4255    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527    1.3353    0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    1.8933    1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063    0.9019    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238    2.2523    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579    2.9800   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037   -0.0024    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -1.3793    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191   -2.3548    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -1.9928    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8865   -0.6346    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.2914    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940    1.0246    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327    1.9940    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    1.6952    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.3741    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4913   -3.5903    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -3.3149    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -4.1275    0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745   -1.8522    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207   -1.1602   -2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -1.3370   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -2.7615   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    1.4420    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.7775    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2003    2.9873    1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4244   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2437    2.9352   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    3.9962   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -2.7473    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.0969    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6563    1.2504    0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    3.0139    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    2.5138    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -4.5200    0.2444 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  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  3  1  0
 19 10  1  0
 23 11  2  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.608  -4.189   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.203  -2.838   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.473  -1.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.742  -0.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.095  -1.216   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.310  -0.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.310   1.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.662   1.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.662   3.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.310   4.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.959   3.378   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.959   1.891   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.742   1.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.743   1.621   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.013   3.108   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.365   3.919   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.662   0.406   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.311   1.351   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.959   0.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.824  -0.811   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.175  -1.621   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.528  -0.811   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -1.688  -2.703   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13    4   12   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   17   19                                                       
CONECT   19   14   18   20                                                  
CONECT   20    3   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    2    5                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0038584
HETATM    1  C1  UNL     1      -3.867  -1.701  -1.228  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.281  -1.432   0.024  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.990  -0.920   0.072  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.741   0.425   0.065  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.753   1.335   0.010  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.405   1.893   1.130  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.406   0.902   0.115  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.224   2.252   0.090  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.258   2.980  -1.168  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.604  -0.002   0.176  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.295  -1.379   0.178  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.219  -2.355   0.231  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.540  -1.993   0.293  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.886  -0.635   0.301  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.221  -0.291   0.408  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.594   1.025   0.464  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.633   1.994   0.413  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.282   1.695   0.304  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.931   0.374   0.245  1.00  0.00           C  
HETATM   20  N1  UNL     1       0.491  -3.590   0.213  1.00  0.00           N  
HETATM   21  C17 UNL     1      -0.901  -3.315   0.147  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.854  -4.128   0.114  1.00  0.00           O  
HETATM   23  C18 UNL     1      -0.975  -1.852   0.127  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.321  -1.160  -2.028  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.926  -1.337  -1.258  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.883  -2.762  -1.495  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.047   1.442   2.080  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.495   1.778   0.975  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.200   2.987   1.127  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.444   2.424  -1.822  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.244   2.935  -1.636  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.155   3.996  -1.026  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.301  -2.747   0.334  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.973  -1.097   0.448  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.656   1.250   0.547  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.953   3.014   0.460  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.634   2.514   0.327  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.957  -4.520   0.244  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5    7
CONECT    5    6
CONECT    6   27   28   29
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   30   31   32
CONECT   10   11   19
CONECT   11   12   23   23
CONECT   12   13   13   20
CONECT   13   14   33
CONECT   14   15   15   19
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   20   21   38
CONECT   21   22   22   23
END

HMDB0038584
     RDKit          3D
Piperolactam C
 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.8670   -1.7013   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2812   -1.4323    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.9203    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7406    0.4255    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527    1.3353    0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    1.8933    1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063    0.9019    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238    2.2523    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579    2.9800   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037   -0.0024    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -1.3793    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191   -2.3548    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -1.9928    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8865   -0.6346    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.2914    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940    1.0246    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327    1.9940    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    1.6952    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.3741    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4913   -3.5903    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -3.3149    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -4.1275    0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745   -1.8522    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207   -1.1602   -2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -1.3370   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -2.7615   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    1.4420    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.7775    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2003    2.9873    1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4244   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2437    2.9352   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    3.9962   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -2.7473    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.0969    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6563    1.2504    0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    3.0139    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    2.5138    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -4.5200    0.2444 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  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  3  1  0
 19 10  1  0
 23 11  2  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3-Trimethoxydibenz[CD,F]indol-4(5H)-one, 9ci	HMDB
O-Methylpiperolactam b	HMDB
Piperolactam b methyl ether	HMDB

Chemical Formula

C₁₈H₁₅NO₄

Average Molecular Weight

309.316

Monoisotopic Molecular Weight

309.100107973

IUPAC Name

13,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

Traditional Name

13,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

CAS Registry Number

116064-76-7

SMILES

COC1=C(OC)C(OC)=C2C3=C1C(=O)NC3=CC1=CC=CC=C21

InChI Identifier

InChI=1S/C18H15NO4/c1-21-15-12-10-7-5-4-6-9(10)8-11-13(12)14(18(20)19-11)16(22-2)17(15)23-3/h4-8H,1-3H3,(H,19,20)

InChI Key

GYYIMUXZCUHECT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aristolactams

Sub Class

Not Available

Direct Parent

Aristolactams

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038584)

Cellular substructure

Membrane (HMDB: HMDB0038584)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038584)

Source

Exogenous

Food

Food (HMDB: HMDB0038584)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038584)

Not Available

Nutrient (HMDB: HMDB0038584)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 188 °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	0.02 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.82 m³·mol⁻¹	ChemAxon
Polarizability	32.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.979	31661259
DarkChem	[M-H]-	173.213	31661259
DeepCCS	[M-2H]-	205.371	30932474
DeepCCS	[M+Na]+	180.936	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	177.1	32859911
AllCCS	[M+Na-2H]-	176.4	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperolactam C	COC1=C(OC)C(OC)=C2C3=C1C(=O)NC3=CC1=CC=CC=C21	4492.8	Standard polar	33892256
Piperolactam C	COC1=C(OC)C(OC)=C2C3=C1C(=O)NC3=CC1=CC=CC=C21	2843.7	Standard non polar	33892256
Piperolactam C	COC1=C(OC)C(OC)=C2C3=C1C(=O)NC3=CC1=CC=CC=C21	3103.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperolactam C,1TMS,isomer #1	COC1=C(OC)C(OC)=C2C3=C1C(=O)N([Si](C)(C)C)C3=CC1=CC=CC=C12	2826.5	Semi standard non polar	33892256
Piperolactam C,1TMS,isomer #1	COC1=C(OC)C(OC)=C2C3=C1C(=O)N([Si](C)(C)C)C3=CC1=CC=CC=C12	2872.6	Standard non polar	33892256
Piperolactam C,1TBDMS,isomer #1	COC1=C(OC)C(OC)=C2C3=C1C(=O)N([Si](C)(C)C(C)(C)C)C3=CC1=CC=CC=C12	3027.4	Semi standard non polar	33892256
Piperolactam C,1TBDMS,isomer #1	COC1=C(OC)C(OC)=C2C3=C1C(=O)N([Si](C)(C)C(C)(C)C)C3=CC1=CC=CC=C12	3046.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piperolactam C GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ox-0091000000-2cf97cdec2835af1b0ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperolactam C GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperolactam C 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 - Piperolactam C 10V, Positive-QTOF	splash10-03di-0009000000-bec20bfda14ddea05c58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 20V, Positive-QTOF	splash10-03di-0029000000-c96b5d78403138edc8e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 40V, Positive-QTOF	splash10-03dl-0090000000-a105e7f5cd07ff9d125d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 10V, Negative-QTOF	splash10-0a4i-0009000000-b640c86b02787bc3f2b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 20V, Negative-QTOF	splash10-0a4l-2059000000-650049adee23decb4ba9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 40V, Negative-QTOF	splash10-0006-8090000000-76e3091094bbe71efed5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 10V, Positive-QTOF	splash10-03di-0009000000-ca0f623accd9ac4b341d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 20V, Positive-QTOF	splash10-03di-0009000000-ca0f623accd9ac4b341d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 40V, Positive-QTOF	splash10-0089-0392000000-7b14b842c7bfb79202fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 10V, Negative-QTOF	splash10-0a4i-0009000000-032c4ad1d38e89ca2312	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 20V, Negative-QTOF	splash10-0a4i-0009000000-032c4ad1d38e89ca2312	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam C 40V, Negative-QTOF	splash10-004j-0090000000-0b02b55a4998484bdfcd	2021-09-25	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

FDB017974

KNApSAcK ID

C00027471

Chemspider ID

9056688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10881419

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Piperolactam C (HMDB0038584)

MOL for HMDB0038584 (Piperolactam C)

3D MOL for HMDB0038584 (Piperolactam C)

3D SDF for HMDB0038584 (Piperolactam C)

3D-SDF for HMDB0038584 (Piperolactam C)

PDB for HMDB0038584 (Piperolactam C)

3D PDB for HMDB0038584 (Piperolactam C)

SMILES for HMDB0038584 (Piperolactam C)

INCHI for HMDB0038584 (Piperolactam C)

Structure for HMDB0038584 (Piperolactam C)

3D Structure for HMDB0038584 (Piperolactam C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra