Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:41:29 UTC

Update Date

2021-09-26 23:00:53 UTC

HMDB ID

HMDB0249806

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cephaeline

Description

Desmethylemetine, also known as cephaelin, belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei. Based on a literature review very few articles have been published on Desmethylemetine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cephaeline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cephaeline 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


  Mrv1533004161508412D          

 34 38  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 22 34  1  0  0  0  0
 26 34  1  0  0  0  0
M  END

HMDB0249806
     RDKit          3D
Cephaeline
 72 76  0  0  0  0  0  0  0  0999 V2000
    1.5626   -1.2860   -4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -1.0987   -3.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -0.7739   -2.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.8691   -2.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.4613   -2.0187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -2.4658   -1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -2.0405   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371   -0.7470   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9761   -0.4389    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    0.7366    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1305    1.0667    1.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2508    0.2241    1.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134    1.5841    0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    2.7720    1.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434    3.6640    1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    1.2861    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.0808   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -0.2158   -1.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.2500   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.3713   -1.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.3435   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.2016    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -1.2399    1.8874 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -1.6433    3.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -0.5357    3.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    0.2755    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    1.3626    3.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360    2.1825    2.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    3.2955    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    1.8504    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330    2.6795    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815    2.3899   -1.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7380    0.7711    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.0216    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -0.8225   -4.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989   -2.3536   -4.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -0.8030   -5.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.2673   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -2.0460   -2.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2664    0.1195   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.1476   -3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -2.7580   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -3.4082   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527   -2.6928   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3504   -2.7715   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.9296   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7960   -1.1531    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7524    0.0784    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.7619    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916    0.6663    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    3.1035    1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    4.4442    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    4.0995    0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    1.9764    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    0.6611   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    0.6663    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218   -1.1106    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.6654   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048   -1.3973   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -2.3705   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -2.0869    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -0.2646    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.7424    3.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -2.6082    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -0.9715    4.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041    0.1573    4.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    1.6074    4.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3467    3.5481    3.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    2.5805   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136    1.3309   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944    3.0037   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.5412   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  2  0
 20  3  1  0
 34 22  1  0
 18  5  1  0
 34 26  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 29 68  1  0
 32 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  1  0
M  END


  Mrv1533004161508412D          

 34 38  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 22 34  1  0  0  0  0
 26 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249806

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3

> <INCHI_KEY>
DTGZHCFJNDAHEN-UHFFFAOYSA-N

> <FORMULA>
C28H38N2O4

> <MOLECULAR_WEIGHT>
466.622

> <EXACT_MASS>
466.283157712

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.85992025062169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-({3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.9667360467999746

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.072601240111634

> <JCHEM_PKA_STRONGEST_BASIC>
9.026392703972926

> <JCHEM_POLAR_SURFACE_AREA>
63.19000000000001

> <JCHEM_REFRACTIVITY>
135.26839999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cephaeline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249806
     RDKit          3D
Cephaeline
 72 76  0  0  0  0  0  0  0  0999 V2000
    1.5626   -1.2860   -4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -1.0987   -3.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -0.7739   -2.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.8691   -2.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.4613   -2.0187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -2.4658   -1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -2.0405   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371   -0.7470   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9761   -0.4389    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    0.7366    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1305    1.0667    1.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2508    0.2241    1.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134    1.5841    0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    2.7720    1.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434    3.6640    1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    1.2861    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.0808   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -0.2158   -1.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.2500   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.3713   -1.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.3435   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.2016    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -1.2399    1.8874 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -1.6433    3.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -0.5357    3.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    0.2755    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    1.3626    3.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360    2.1825    2.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    3.2955    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    1.8504    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330    2.6795    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815    2.3899   -1.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7380    0.7711    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.0216    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -0.8225   -4.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989   -2.3536   -4.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -0.8030   -5.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.2673   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -2.0460   -2.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2664    0.1195   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.1476   -3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -2.7580   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -3.4082   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527   -2.6928   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3504   -2.7715   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.9296   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7960   -1.1531    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7524    0.0784    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.7619    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916    0.6663    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    3.1035    1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    4.4442    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    4.0995    0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    1.9764    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    0.6611   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    0.6663    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218   -1.1106    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.6654   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048   -1.3973   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -2.3705   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -2.0869    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -0.2646    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.7424    3.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -2.6082    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -0.9715    4.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041    0.1573    4.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    1.6074    4.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3467    3.5481    3.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    2.5805   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136    1.3309   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944    3.0037   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.5412   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  2  0
 20  3  1  0
 34 22  1  0
 18  5  1  0
 34 26  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 29 68  1  0
 32 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  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  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   22   26                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0249806
HETATM    1  C1  UNL     1       1.563  -1.286  -4.689  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.959  -1.099  -3.236  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.697  -0.774  -2.486  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.332  -1.869  -2.583  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.566  -1.461  -2.019  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.378  -2.466  -1.423  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.821  -2.041  -1.331  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.837  -0.747  -0.561  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.976  -0.439   0.178  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.996   0.737   0.872  1.00  0.00           C  
HETATM   11  O1  UNL     1      -6.131   1.067   1.622  1.00  0.00           O  
HETATM   12  C10 UNL     1      -7.251   0.224   1.682  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.913   1.584   0.833  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.030   2.772   1.582  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.943   3.664   1.567  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.807   1.286   0.116  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.775   0.081  -0.601  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.549  -0.216  -1.370  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.388  -0.250  -0.350  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.949  -0.371  -1.038  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.867  -1.344  -0.418  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.286  -1.202   0.968  1.00  0.00           C  
HETATM   23  N2  UNL     1       1.147  -1.240   1.887  1.00  0.00           N  
HETATM   24  C20 UNL     1       1.614  -1.643   3.219  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.449  -0.536   3.756  1.00  0.00           C  
HETATM   26  C22 UNL     1       3.139   0.276   2.689  1.00  0.00           C  
HETATM   27  C23 UNL     1       3.859   1.363   3.125  1.00  0.00           C  
HETATM   28  C24 UNL     1       4.536   2.183   2.248  1.00  0.00           C  
HETATM   29  O3  UNL     1       5.276   3.296   2.665  1.00  0.00           O  
HETATM   30  C25 UNL     1       4.450   1.850   0.912  1.00  0.00           C  
HETATM   31  O4  UNL     1       5.133   2.680   0.035  1.00  0.00           O  
HETATM   32  C26 UNL     1       5.082   2.390  -1.344  1.00  0.00           C  
HETATM   33  C27 UNL     1       3.738   0.771   0.452  1.00  0.00           C  
HETATM   34  C28 UNL     1       3.078  -0.022   1.349  1.00  0.00           C  
HETATM   35  H1  UNL     1       0.590  -0.823  -4.922  1.00  0.00           H  
HETATM   36  H2  UNL     1       1.499  -2.354  -4.959  1.00  0.00           H  
HETATM   37  H3  UNL     1       2.311  -0.803  -5.352  1.00  0.00           H  
HETATM   38  H4  UNL     1       2.653  -0.267  -3.139  1.00  0.00           H  
HETATM   39  H5  UNL     1       2.443  -2.046  -2.931  1.00  0.00           H  
HETATM   40  H6  UNL     1       0.266   0.120  -3.031  1.00  0.00           H  
HETATM   41  H7  UNL     1      -0.530  -2.148  -3.642  1.00  0.00           H  
HETATM   42  H8  UNL     1       0.072  -2.758  -2.045  1.00  0.00           H  
HETATM   43  H9  UNL     1      -2.291  -3.408  -1.973  1.00  0.00           H  
HETATM   44  H10 UNL     1      -2.053  -2.693  -0.367  1.00  0.00           H  
HETATM   45  H11 UNL     1      -4.350  -2.772  -0.689  1.00  0.00           H  
HETATM   46  H12 UNL     1      -4.273  -1.930  -2.328  1.00  0.00           H  
HETATM   47  H13 UNL     1      -5.796  -1.153   0.165  1.00  0.00           H  
HETATM   48  H14 UNL     1      -7.752   0.078   0.706  1.00  0.00           H  
HETATM   49  H15 UNL     1      -6.887  -0.762   2.085  1.00  0.00           H  
HETATM   50  H16 UNL     1      -7.992   0.666   2.378  1.00  0.00           H  
HETATM   51  H17 UNL     1      -2.035   3.104   1.835  1.00  0.00           H  
HETATM   52  H18 UNL     1      -3.118   4.444   2.333  1.00  0.00           H  
HETATM   53  H19 UNL     1      -2.822   4.099   0.552  1.00  0.00           H  
HETATM   54  H20 UNL     1      -1.971   1.976   0.105  1.00  0.00           H  
HETATM   55  H21 UNL     1      -1.410   0.661  -2.049  1.00  0.00           H  
HETATM   56  H22 UNL     1      -0.434   0.666   0.280  1.00  0.00           H  
HETATM   57  H23 UNL     1      -0.622  -1.111   0.306  1.00  0.00           H  
HETATM   58  H24 UNL     1       1.347   0.665  -1.105  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.805  -1.397  -1.060  1.00  0.00           H  
HETATM   60  H26 UNL     1       1.420  -2.371  -0.586  1.00  0.00           H  
HETATM   61  H27 UNL     1       2.914  -2.087   1.294  1.00  0.00           H  
HETATM   62  H28 UNL     1       0.780  -0.265   2.051  1.00  0.00           H  
HETATM   63  H29 UNL     1       0.710  -1.742   3.841  1.00  0.00           H  
HETATM   64  H30 UNL     1       2.123  -2.608   3.124  1.00  0.00           H  
HETATM   65  H31 UNL     1       3.274  -0.972   4.365  1.00  0.00           H  
HETATM   66  H32 UNL     1       1.904   0.157   4.427  1.00  0.00           H  
HETATM   67  H33 UNL     1       3.914   1.607   4.190  1.00  0.00           H  
HETATM   68  H34 UNL     1       5.347   3.548   3.638  1.00  0.00           H  
HETATM   69  H35 UNL     1       4.036   2.581  -1.679  1.00  0.00           H  
HETATM   70  H36 UNL     1       5.314   1.331  -1.576  1.00  0.00           H  
HETATM   71  H37 UNL     1       5.794   3.004  -1.930  1.00  0.00           H  
HETATM   72  H38 UNL     1       3.694   0.541  -0.620  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   20   40
CONECT    4    5   41   42
CONECT    5    6   18
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9    9   17
CONECT    9   10   47
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   48   49   50
CONECT   13   14   16
CONECT   14   15
CONECT   15   51   52   53
CONECT   16   17   17   54
CONECT   17   18
CONECT   18   19   55
CONECT   19   20   56   57
CONECT   20   21   58
CONECT   21   22   59   60
CONECT   22   23   34   61
CONECT   23   24   62
CONECT   24   25   63   64
CONECT   25   26   65   66
CONECT   26   27   27   34
CONECT   27   28   67
CONECT   28   29   30   30
CONECT   29   68
CONECT   30   31   33
CONECT   31   32
CONECT   32   69   70   71
CONECT   33   34   34   72
END

HMDB0249806
     RDKit          3D
Cephaeline
 72 76  0  0  0  0  0  0  0  0999 V2000
    1.5626   -1.2860   -4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -1.0987   -3.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -0.7739   -2.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.8691   -2.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.4613   -2.0187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -2.4658   -1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -2.0405   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371   -0.7470   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9761   -0.4389    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    0.7366    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1305    1.0667    1.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2508    0.2241    1.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134    1.5841    0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    2.7720    1.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434    3.6640    1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    1.2861    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.0808   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -0.2158   -1.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.2500   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.3713   -1.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.3435   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.2016    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -1.2399    1.8874 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -1.6433    3.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -0.5357    3.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    0.2755    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    1.3626    3.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360    2.1825    2.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    3.2955    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    1.8504    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330    2.6795    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815    2.3899   -1.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7380    0.7711    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.0216    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -0.8225   -4.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989   -2.3536   -4.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -0.8030   -5.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.2673   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -2.0460   -2.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2664    0.1195   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.1476   -3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -2.7580   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -3.4082   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527   -2.6928   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3504   -2.7715   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.9296   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7960   -1.1531    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7524    0.0784    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.7619    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916    0.6663    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    3.1035    1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    4.4442    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    4.0995    0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    1.9764    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    0.6611   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    0.6663    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218   -1.1106    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.6654   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048   -1.3973   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -2.3705   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -2.0869    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -0.2646    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.7424    3.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -2.6082    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -0.9715    4.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041    0.1573    4.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    1.6074    4.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3467    3.5481    3.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    2.5805   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136    1.3309   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944    3.0037   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.5412   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  2  0
 20  3  1  0
 34 22  1  0
 18  5  1  0
 34 26  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 29 68  1  0
 32 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cephaelin	MeSH
Cephaline	MeSH
Desmethyl-emetine	MeSH
Desmethylemetine	MeSH

Chemical Formula

C₂₈H₃₈N₂O₄

Average Molecular Weight

466.622

Monoisotopic Molecular Weight

466.283157712

IUPAC Name

1-({3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

Traditional Name

cephaeline

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12

InChI Identifier

InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3

InChI Key

DTGZHCFJNDAHEN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Emetine alkaloids

Sub Class

Not Available

Direct Parent

Emetine alkaloids

Alternative Parents

Substituents

Emetine alkaloid
Quinolizidine
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Amine
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
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)

Source

Exogenous

Exogenous (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	4.1	ALOGPS
logP	3.97	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.19 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.27 m³·mol⁻¹	ChemAxon
Polarizability	53.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	242.923	30932474
DeepCCS	[M+Na]+	218.151	30932474
AllCCS	[M+H]+	216.2	32859911
AllCCS	[M+H-H2O]+	214.4	32859911
AllCCS	[M+NH4]+	217.9	32859911
AllCCS	[M+Na]+	218.3	32859911
AllCCS	[M-H]-	206.6	32859911
AllCCS	[M+Na-2H]-	207.8	32859911
AllCCS	[M+HCOO]-	209.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.5955 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.72 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1294.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	160.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	392.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	363.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	619.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	792.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	337.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1026.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	448.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	530.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	18.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cephaeline	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12	4495.3	Standard polar	33892256
Cephaeline	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12	3776.9	Standard non polar	33892256
Cephaeline	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12	4036.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cephaeline,2TMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	3867.8	Semi standard non polar	33892256
Cephaeline,2TMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	4057.3	Standard non polar	33892256
Cephaeline,2TMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	4757.5	Standard polar	33892256
Cephaeline,1TBDMS,isomer #2	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C	4117.5	Semi standard non polar	33892256
Cephaeline,1TBDMS,isomer #2	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C	4230.2	Standard non polar	33892256
Cephaeline,1TBDMS,isomer #2	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C	5099.0	Standard polar	33892256
Cephaeline,2TBDMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	4284.9	Semi standard non polar	33892256
Cephaeline,2TBDMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	4483.0	Standard non polar	33892256
Cephaeline,2TBDMS,isomer #1	CCC1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1CC1C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	4918.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cephaeline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi1-0980500000-9e89169bc34e697693bb	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephaeline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephaeline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephaeline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephaeline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cephaeline 6V, Positive-QTOF	splash10-014i-0020900000-e24ad5f6bb0311ba4c00	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 10V, Positive-QTOF	splash10-014i-0000900000-a40eaed843bb1ad77873	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 20V, Positive-QTOF	splash10-014i-0020900000-cde6b73af91fb65e6d46	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 40V, Positive-QTOF	splash10-06rf-1692400000-fb940feccfb65b6de7f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 10V, Negative-QTOF	splash10-014i-0000900000-ff3c1a63776dd83812d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 20V, Negative-QTOF	splash10-014i-0000900000-22e228998e07b2107bf3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephaeline 40V, Negative-QTOF	splash10-03fr-0313900000-432caa7cf8b1ab1a2a9f	2021-10-12	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

2564

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cephaeline

METLIN ID

Not Available

PubChem Compound

2665

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 Cephaeline (HMDB0249806)

MOL for HMDB0249806 (Cephaeline)

3D MOL for HMDB0249806 (Cephaeline)

3D SDF for HMDB0249806 (Cephaeline)

3D-SDF for HMDB0249806 (Cephaeline)

PDB for HMDB0249806 (Cephaeline)

3D PDB for HMDB0249806 (Cephaeline)

SMILES for HMDB0249806 (Cephaeline)

INCHI for HMDB0249806 (Cephaeline)

Structure for HMDB0249806 (Cephaeline)

3D Structure for HMDB0249806 (Cephaeline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra