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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:30 UTC

Update Date

2022-03-07 02:53:34 UTC

HMDB ID

HMDB0033060

Secondary Accession Numbers

HMDB33060

Metabolite Identification

Common Name

Piperolactam A

Description

Piperolactam A, also known as aristolactam F1, 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 A is an extremely weak basic (essentially neutral) compound (based on its pKa). Alkaloid from roots of Piper longum (long pepper).

Structure

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

HMDB0033060
     RDKit          3D
Piperolactam A
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -0.9198    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2544   -1.3075    0.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -0.4448    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362    0.9175    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.7821    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    1.1895    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666    2.1002   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2534    1.6296   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    0.2563   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.2099   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.5517   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.4452   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -2.0315   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -0.6865   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -0.1975   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.0437    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -2.3863    0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    3.4035    0.0143 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621    3.2304    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9498    4.1087    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.6840   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9561   -0.9895    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    0.0459   -0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.3550    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    2.3122   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    0.5426   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0869   -1.8802   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740   -3.5038   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -2.7982   -0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -3.0803    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8863    4.2868   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 16  3  1  0
 19  5  1  0
 15  6  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv0541 02241214572D          

 20 23  0  0  0  0            999 V2000
    0.7794   -1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -2.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -0.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794   -1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -0.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    1.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    1.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659    1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    1.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    0.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659    0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    0.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    0.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5769    1.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775    0.7142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932    2.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8 13  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 20  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033060

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19)

> <INCHI_KEY>
KBGNBPGXVKPRQI-UHFFFAOYSA-N

> <FORMULA>
C16H11NO3

> <MOLECULAR_WEIGHT>
265.2634

> <EXACT_MASS>
265.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.374795962500897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2(7),3,5,8,12(16),13-heptaen-11-one

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.6096017316666664

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.98757127562766

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.557652923136493

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20864257671271

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
76.87799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2(7),3,5,8,12(16),13-heptaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033060
     RDKit          3D
Piperolactam A
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -0.9198    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2544   -1.3075    0.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -0.4448    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362    0.9175    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.7821    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    1.1895    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666    2.1002   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2534    1.6296   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    0.2563   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.2099   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.5517   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.4452   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -2.0315   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -0.6865   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -0.1975   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.0437    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -2.3863    0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    3.4035    0.0143 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621    3.2304    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9498    4.1087    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.6840   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9561   -0.9895    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    0.0459   -0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.3550    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    2.3122   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    0.5426   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0869   -1.8802   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740   -3.5038   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -2.7982   -0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -3.0803    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8863    4.2868   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 16  3  1  0
 19  5  1  0
 15  6  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  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  C   UNK     0       1.455  -3.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.123  -4.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.211  -3.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.211  -2.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.123  -1.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.455  -2.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.790  -1.295   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.790   0.245   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.546   3.325   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.211   2.555   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.123   3.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.455   2.555   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.455   1.015   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.123   0.245   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.211   1.015   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.546   0.245   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.944   2.953   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.878   1.333   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       3.534   4.375   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.878   2.552   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7   13   18                                                  
CONECT    9   10   20                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   14                                                  
CONECT   14    5   13   15                                                  
CONECT   15   10   14   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18   19                                                  
CONECT   18    8   17                                                       
CONECT   19   17                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0033060
HETATM    1  C1  UNL     1       4.586  -0.920   0.339  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.254  -1.308   0.234  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.179  -0.445   0.162  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.336   0.917   0.190  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.263   1.782   0.118  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.032   1.190   0.018  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.967   2.100  -0.047  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.253   1.630  -0.150  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.482   0.256  -0.183  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.785  -0.210  -0.287  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.062  -1.552  -0.324  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.023  -2.445  -0.255  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.706  -2.031  -0.151  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.460  -0.687  -0.117  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.166  -0.198  -0.013  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.904  -1.044   0.059  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.786  -2.386   0.034  1.00  0.00           O  
HETATM   18  N1  UNL     1      -0.358   3.403   0.014  1.00  0.00           N  
HETATM   19  C16 UNL     1       1.062   3.230   0.120  1.00  0.00           C  
HETATM   20  O3  UNL     1       1.950   4.109   0.197  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.194  -1.684  -0.228  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.956  -0.990   1.388  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.829   0.046  -0.113  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.312   1.355   0.269  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.073   2.312  -0.204  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.570   0.543  -0.338  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.087  -1.880  -0.406  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.274  -3.504  -0.287  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.980  -2.798  -0.105  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.489  -3.080   0.079  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.886   4.287  -0.016  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   24
CONECT    5    6    6   19
CONECT    6    7   15
CONECT    7    8    8   18
CONECT    8    9   25
CONECT    9   10   10   14
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15
CONECT   15   16   16
CONECT   16   17
CONECT   17   30
CONECT   18   19   31
CONECT   19   20   20
END

HMDB0033060
     RDKit          3D
Piperolactam A
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -0.9198    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2544   -1.3075    0.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -0.4448    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362    0.9175    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.7821    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    1.1895    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666    2.1002   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2534    1.6296   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    0.2563   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.2099   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.5517   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.4452   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -2.0315   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -0.6865   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -0.1975   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.0437    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -2.3863    0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    3.4035    0.0143 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621    3.2304    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9498    4.1087    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.6840   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9561   -0.9895    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    0.0459   -0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.3550    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    2.3122   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    0.5426   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0869   -1.8802   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740   -3.5038   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -2.7982   -0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -3.0803    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8863    4.2868   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 16  3  1  0
 19  5  1  0
 15  6  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-2-methoxy-dibenz(CD,F)indol-4(5H)-one	HMDB
1-Hydroxy-2-methoxy-dibenz[CD,F]indol-4(5H)-one	HMDB
1-Hydroxy-2-methoxydibenz(CD,F)indol-4(5H)-one	HMDB
1-Hydroxy-2-methoxydibenz[CD,F]indol-4(5H)-one, 9ci	HMDB
Aristolactam F1	HMDB
Piperolactam a	MeSH

Chemical Formula

C₁₆H₁₁NO₃

Average Molecular Weight

265.2634

Monoisotopic Molecular Weight

265.073893223

IUPAC Name

15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2(7),3,5,8,12(16),13-heptaen-11-one

Traditional Name

15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2(7),3,5,8,12(16),13-heptaen-11-one

CAS Registry Number

112501-42-5

SMILES

COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O

InChI Identifier

InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19)

InChI Key

KBGNBPGXVKPRQI-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

Substituents

Aristolactam
Phenanthrol
Phenanthrene
1-naphthol
Isoindolone
Naphthalene
Indole or derivatives
Isoindole or derivatives
Anisole
Alkyl aryl ether
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033060)

Cellular substructure

Membrane (HMDB: HMDB0033060)

Source

Exogenous

Food

Food (HMDB: HMDB0033060)

Not Available

Nutrient (HMDB: HMDB0033060)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	303 - 306 °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	0.074 g/L	ALOGPS
logP	2.94	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	27.37 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]+	160.26	31661259
DarkChem	[M-H]-	159.582	31661259
DeepCCS	[M+H]+	163.125	30932474
DeepCCS	[M-H]-	160.767	30932474
DeepCCS	[M-2H]-	194.183	30932474
DeepCCS	[M+Na]+	169.41	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.7	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	164.1	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperolactam A	COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O	4436.3	Standard polar	33892256
Piperolactam A	COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O	2713.0	Standard non polar	33892256
Piperolactam A	COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O	3152.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperolactam A,1TMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C)NC2=O	2924.5	Semi standard non polar	33892256
Piperolactam A,1TMS,isomer #2	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O)N([Si](C)(C)C)C2=O	2891.0	Semi standard non polar	33892256
Piperolactam A,2TMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C)N([Si](C)(C)C)C2=O	2871.0	Semi standard non polar	33892256
Piperolactam A,2TMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C)N([Si](C)(C)C)C2=O	2818.8	Standard non polar	33892256
Piperolactam A,1TBDMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C(C)(C)C)NC2=O	3115.6	Semi standard non polar	33892256
Piperolactam A,1TBDMS,isomer #2	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O)N([Si](C)(C)C(C)(C)C)C2=O	3094.6	Semi standard non polar	33892256
Piperolactam A,2TBDMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3256.7	Semi standard non polar	33892256
Piperolactam A,2TBDMS,isomer #1	COC1=CC2=C3C(=CC4=CC=CC=C4C3=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3231.6	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rj-0090000000-ff79267afee113bc1287	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperolactam A GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8098000000-46f3e57aaf64847b2b23	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperolactam A 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 A 10V, Positive-QTOF	splash10-014i-0090000000-954f1940b8ea56fa1bfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 20V, Positive-QTOF	splash10-014i-0090000000-c70c33283416173be427	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 40V, Positive-QTOF	splash10-0002-0090000000-605a25317035bf2305b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 10V, Negative-QTOF	splash10-03di-0090000000-ecc206a6e6ac7b7369f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 20V, Negative-QTOF	splash10-03di-1090000000-c7c72d35ecbb13e6fbe4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 40V, Negative-QTOF	splash10-052f-8090000000-47858ab047ad6ccadfd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 10V, Positive-QTOF	splash10-014i-0090000000-658a10b0ee8a282b5eed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 20V, Positive-QTOF	splash10-014i-0090000000-658a10b0ee8a282b5eed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 40V, Positive-QTOF	splash10-0hnv-0290000000-ca1278bcd8866f766b7e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 10V, Negative-QTOF	splash10-03di-0090000000-0c9cfff5026dde1688c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 20V, Negative-QTOF	splash10-03di-0090000000-1f1833da6ac8b65143fd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperolactam A 40V, Negative-QTOF	splash10-001j-0190000000-c8885a43b35a69df1a4d	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

FDB011053

KNApSAcK ID

C00027470

Chemspider ID

2338707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3081016

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 A (HMDB0033060)

MOL for HMDB0033060 (Piperolactam A)

3D MOL for HMDB0033060 (Piperolactam A)

3D SDF for HMDB0033060 (Piperolactam A)

3D-SDF for HMDB0033060 (Piperolactam A)

PDB for HMDB0033060 (Piperolactam A)

3D PDB for HMDB0033060 (Piperolactam A)

SMILES for HMDB0033060 (Piperolactam A)

INCHI for HMDB0033060 (Piperolactam A)

Structure for HMDB0033060 (Piperolactam A)

3D Structure for HMDB0033060 (Piperolactam A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra