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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:24:52 UTC

Update Date

2021-09-26 23:08:03 UTC

HMDB ID

HMDB0254221

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lurtotecan

Description

Lurtotecan belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). Based on a literature review a significant number of articles have been published on Lurtotecan. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lurtotecan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lurtotecan 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

  Mrv1652309112115252D          

 38 44  0  0  0  0            999 V2000
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   -3.7816   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6491   -4.3922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -3.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0254221
     RDKit          3D
Lurtotecan
 68 74  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv1652309112115252D          

 38 44  0  0  0  0            999 V2000
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 14 15  2  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
  3 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254221

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C(CN4CCN(C)CC4)C4=CC5=C(OCCO5)C=C4N=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3

> <INCHI_KEY>
RVFGKBWWUQOIOU-UHFFFAOYSA-N

> <FORMULA>
C28H30N4O6

> <MOLECULAR_WEIGHT>
518.57

> <EXACT_MASS>
518.216534702

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.18676977868556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,24}.0^{17,22}]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
0.5218921093333335

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.71059750794143

> <JCHEM_PKA_STRONGEST_BASIC>
7.861537251238798

> <JCHEM_POLAR_SURFACE_AREA>
104.67

> <JCHEM_REFRACTIVITY>
140.0427

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,24}.0^{17,22}]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254221
     RDKit          3D
Lurtotecan
 68 74  0  0  0  0  0  0  0  0999 V2000
    7.5698    0.2037    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703    0.1358    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -1.2283   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9648   -1.4721   -1.5088 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177   -2.3111    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1714   -2.0501    1.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7116   -3.5936    0.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4010   -3.8118    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -2.5916    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -1.3724   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090   -0.2634   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -0.3683    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -1.5672    0.3407 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -2.7006    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -3.8457    0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -1.3863    0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694    0.0156    0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    0.6600    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420    1.9985   -0.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2050    2.7030   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292    4.0561   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    4.8783   -0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    4.2669    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    2.9191    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    2.0743    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    0.7419    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    0.0297    0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887   -1.1143    0.1390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001   -1.1865   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -1.8159   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1470   -2.8036   -0.7950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -3.9599   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -3.2630    0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255   -2.1379    1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5266    5.1490    0.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    6.4295    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247    7.0517    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273    6.2379   -0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9817   -0.7177   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0470    0.4878    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8593    1.0183   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878    0.3516    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6624    0.8586   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5059   -0.8227   -2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -4.5011    0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -4.3731   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.7050   -0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.8358    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -1.9974   -0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308    4.5041   -0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194    2.4983    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437    0.7126    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4756   -0.2948    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2798   -0.1373   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -1.6715   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043   -2.2760   -2.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3262   -0.9794   -1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4672   -3.8865   -2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7360   -4.1482   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1394   -4.9100   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -4.0355   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536   -3.7729    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312   -1.6598    1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -2.5450    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053    6.3187    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    7.1305    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913    8.0562   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935    7.2155    1.4411 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 23 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 10  3  1  0
 18 12  1  0
 25 20  1  0
 34 28  1  0
 14  9  1  0
 26 17  1  0
 38 22  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  4 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 16 48  1  0
 16 49  1  0
 21 50  1  0
 24 51  1  0
 27 52  1  0
 27 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
 33 61  1  0
 33 62  1  0
 34 63  1  0
 34 64  1  0
 36 65  1  0
 36 66  1  0
 37 67  1  0
 37 68  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -6.031  -3.942   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.059  -5.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.580  -6.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.629  -7.764   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.203  -9.193   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.728  -9.410   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.678  -8.199   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.104  -6.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.055  -5.558   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.252 -10.404   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.826 -11.833   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -3.728 -10.187   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.546 -11.174   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.242 -10.355   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.240 -10.776   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.345  -9.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.826 -10.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.932  -9.053   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.556  -7.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.075  -7.139   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.969  -8.211   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.512  -7.790   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.617  -8.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.154  -8.758   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.105  -7.546   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.662  -6.488   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.143  -6.909   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.519  -8.403   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.413  -9.475   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.615 -12.270   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -0.490 -13.342   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -0.114 -14.835   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.220 -15.908   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -2.701 -15.486   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -3.077 -13.993   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.971 -12.921   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.807 -16.558   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.222  -5.826   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   38                                             
CONECT    4    3    5   25                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   14   24                                                  
CONECT   24   23   12   25                                                  
CONECT   25   24    4                                                       
CONECT   26   19   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   18                                                       
CONECT   30   15   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38    3                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

COMPND    HMDB0254221
HETATM    1  C1  UNL     1       7.570   0.204   0.126  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.070   0.136   0.227  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.604  -1.228  -0.201  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.965  -1.472  -1.509  1.00  0.00           O  
HETATM    5  C4  UNL     1       6.218  -2.311   0.625  1.00  0.00           C  
HETATM    6  O2  UNL     1       7.171  -2.050   1.373  1.00  0.00           O  
HETATM    7  O3  UNL     1       5.712  -3.594   0.539  1.00  0.00           O  
HETATM    8  C5  UNL     1       4.401  -3.812   0.118  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.560  -2.592   0.138  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.132  -1.372  -0.074  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.309  -0.263  -0.076  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.950  -0.368   0.132  1.00  0.00           C  
HETATM   13  N1  UNL     1       1.408  -1.567   0.341  1.00  0.00           N  
HETATM   14  C10 UNL     1       2.187  -2.701   0.348  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.695  -3.846   0.541  1.00  0.00           O  
HETATM   16  C11 UNL     1       0.005  -1.386   0.566  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.269   0.016   0.396  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.918   0.660   0.157  1.00  0.00           C  
HETATM   19  N2  UNL     1       0.942   1.998  -0.055  1.00  0.00           N  
HETATM   20  C14 UNL     1      -0.205   2.703  -0.032  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.129   4.056  -0.219  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.232   4.878  -0.184  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.460   4.267   0.055  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.554   2.919   0.241  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.428   2.074   0.208  1.00  0.00           C  
HETATM   26  C20 UNL     1      -1.472   0.742   0.422  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.659   0.030   0.830  1.00  0.00           C  
HETATM   28  N3  UNL     1      -3.089  -1.114   0.139  1.00  0.00           N  
HETATM   29  C22 UNL     1      -3.300  -1.187  -1.219  1.00  0.00           C  
HETATM   30  C23 UNL     1      -4.585  -1.816  -1.643  1.00  0.00           C  
HETATM   31  N4  UNL     1      -5.147  -2.804  -0.795  1.00  0.00           N  
HETATM   32  C24 UNL     1      -5.661  -3.960  -1.474  1.00  0.00           C  
HETATM   33  C25 UNL     1      -4.272  -3.263   0.263  1.00  0.00           C  
HETATM   34  C26 UNL     1      -3.626  -2.138   1.000  1.00  0.00           C  
HETATM   35  O5  UNL     1      -3.527   5.149   0.082  1.00  0.00           O  
HETATM   36  C27 UNL     1      -3.360   6.429   0.717  1.00  0.00           C  
HETATM   37  C28 UNL     1      -2.025   7.052   0.466  1.00  0.00           C  
HETATM   38  O6  UNL     1      -1.227   6.238  -0.365  1.00  0.00           O  
HETATM   39  H1  UNL     1       7.982  -0.718  -0.303  1.00  0.00           H  
HETATM   40  H2  UNL     1       8.047   0.488   1.092  1.00  0.00           H  
HETATM   41  H3  UNL     1       7.859   1.018  -0.592  1.00  0.00           H  
HETATM   42  H4  UNL     1       5.688   0.352   1.256  1.00  0.00           H  
HETATM   43  H5  UNL     1       5.662   0.859  -0.526  1.00  0.00           H  
HETATM   44  H6  UNL     1       5.506  -0.823  -2.127  1.00  0.00           H  
HETATM   45  H7  UNL     1       3.935  -4.501   0.883  1.00  0.00           H  
HETATM   46  H8  UNL     1       4.329  -4.373  -0.848  1.00  0.00           H  
HETATM   47  H9  UNL     1       3.708   0.705  -0.249  1.00  0.00           H  
HETATM   48  H10 UNL     1      -0.304  -1.836   1.532  1.00  0.00           H  
HETATM   49  H11 UNL     1      -0.505  -1.997  -0.243  1.00  0.00           H  
HETATM   50  H12 UNL     1       0.831   4.504  -0.403  1.00  0.00           H  
HETATM   51  H13 UNL     1      -3.519   2.498   0.403  1.00  0.00           H  
HETATM   52  H14 UNL     1      -3.544   0.713   0.928  1.00  0.00           H  
HETATM   53  H15 UNL     1      -2.476  -0.295   1.914  1.00  0.00           H  
HETATM   54  H16 UNL     1      -3.280  -0.137  -1.662  1.00  0.00           H  
HETATM   55  H17 UNL     1      -2.418  -1.671  -1.752  1.00  0.00           H  
HETATM   56  H18 UNL     1      -4.404  -2.276  -2.666  1.00  0.00           H  
HETATM   57  H19 UNL     1      -5.326  -0.979  -1.820  1.00  0.00           H  
HETATM   58  H20 UNL     1      -5.467  -3.887  -2.570  1.00  0.00           H  
HETATM   59  H21 UNL     1      -6.736  -4.148  -1.235  1.00  0.00           H  
HETATM   60  H22 UNL     1      -5.139  -4.910  -1.152  1.00  0.00           H  
HETATM   61  H23 UNL     1      -3.559  -4.035  -0.056  1.00  0.00           H  
HETATM   62  H24 UNL     1      -4.954  -3.773   1.018  1.00  0.00           H  
HETATM   63  H25 UNL     1      -4.331  -1.660   1.746  1.00  0.00           H  
HETATM   64  H26 UNL     1      -2.803  -2.545   1.605  1.00  0.00           H  
HETATM   65  H27 UNL     1      -3.505   6.319   1.824  1.00  0.00           H  
HETATM   66  H28 UNL     1      -4.182   7.131   0.356  1.00  0.00           H  
HETATM   67  H29 UNL     1      -2.191   8.056  -0.002  1.00  0.00           H  
HETATM   68  H30 UNL     1      -1.493   7.216   1.441  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   42   43
CONECT    3    4    5   10
CONECT    4   44
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   45   46
CONECT    9   10   10   14
CONECT   10   11
CONECT   11   12   12   47
CONECT   12   13   18
CONECT   13   14   16
CONECT   14   15   15
CONECT   16   17   48   49
CONECT   17   18   18   26
CONECT   18   19
CONECT   19   20   20
CONECT   20   21   25
CONECT   21   22   22   50
CONECT   22   23   38
CONECT   23   24   24   35
CONECT   24   25   51
CONECT   25   26   26
CONECT   26   27
CONECT   27   28   52   53
CONECT   28   29   34
CONECT   29   30   54   55
CONECT   30   31   56   57
CONECT   31   32   33
CONECT   32   58   59   60
CONECT   33   34   61   62
CONECT   34   63   64
CONECT   35   36
CONECT   36   37   65   66
CONECT   37   38   67   68
END

HMDB0254221
     RDKit          3D
Lurtotecan
 68 74  0  0  0  0  0  0  0  0999 V2000
    7.5698    0.2037    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703    0.1358    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -1.2283   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9648   -1.4721   -1.5088 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177   -2.3111    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1714   -2.0501    1.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7116   -3.5936    0.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4010   -3.8118    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -2.5916    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -1.3724   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090   -0.2634   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -0.3683    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -1.5672    0.3407 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -2.7006    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -3.8457    0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -1.3863    0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694    0.0156    0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    0.6600    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420    1.9985   -0.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2050    2.7030   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292    4.0561   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    4.8783   -0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    4.2669    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    2.9191    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    2.0743    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    0.7419    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    0.0297    0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887   -1.1143    0.1390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001   -1.1865   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -1.8159   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1470   -2.8036   -0.7950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -3.9599   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -3.2630    0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255   -2.1379    1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5266    5.1490    0.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    6.4295    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247    7.0517    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273    6.2379   -0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9817   -0.7177   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0470    0.4878    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8593    1.0183   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878    0.3516    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6624    0.8586   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5059   -0.8227   -2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -4.5011    0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -4.3731   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.7050   -0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.8358    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -1.9974   -0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308    4.5041   -0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194    2.4983    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437    0.7126    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4756   -0.2948    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2798   -0.1373   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -1.6715   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043   -2.2760   -2.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3262   -0.9794   -1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4672   -3.8865   -2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7360   -4.1482   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1394   -4.9100   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -4.0355   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536   -3.7729    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312   -1.6598    1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -2.5450    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053    6.3187    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    7.1305    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913    8.0562   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935    7.2155    1.4411 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 23 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 10  3  1  0
 18 12  1  0
 25 20  1  0
 34 28  1  0
 14  9  1  0
 26 17  1  0
 38 22  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  4 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 16 48  1  0
 16 49  1  0
 21 50  1  0
 24 51  1  0
 27 52  1  0
 27 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
 33 61  1  0
 33 62  1  0
 34 63  1  0
 34 64  1  0
 36 65  1  0
 36 66  1  0
 37 67  1  0
 37 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀N₄O₆

Average Molecular Weight

518.57

Monoisotopic Molecular Weight

518.216534702

IUPAC Name

18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,24}.0^{17,22}]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

Traditional Name

18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,24}.0^{17,22}]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

CAS Registry Number

Not Available

SMILES

CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C(CN4CCN(C)CC4)C4=CC5=C(OCCO5)C=C4N=C13)C2=O

InChI Identifier

InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3

InChI Key

RVFGKBWWUQOIOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Benzo-1,4-dioxane
Benzodioxane
Pyranopyridine
Quinoline
Alkyl aryl ether
Pyridinone
Aralkylamine
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Para-dioxin
Piperazine
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Lactone
Lactam
Carboxylic acid ester
Azacycle
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Amine
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen 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 (HMDB: HMDB0254221)

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	1.66	ALOGPS
logP	0.52	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	7.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	104.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.04 m³·mol⁻¹	ChemAxon
Polarizability	56.19 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	252.103	30932474
DeepCCS	[M+Na]+	227.528	30932474
AllCCS	[M+H]+	219.0	32859911
AllCCS	[M+H-H2O]+	217.1	32859911
AllCCS	[M+NH4]+	220.7	32859911
AllCCS	[M+Na]+	221.2	32859911
AllCCS	[M-H]-	221.7	32859911
AllCCS	[M+Na-2H]-	223.0	32859911
AllCCS	[M+HCOO]-	224.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lurtotecan	CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C(CN4CCN(C)CC4)C4=CC5=C(OCCO5)C=C4N=C13)C2=O	4677.7	Standard polar	33892256
Lurtotecan	CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C(CN4CCN(C)CC4)C4=CC5=C(OCCO5)C=C4N=C13)C2=O	4057.7	Standard non polar	33892256
Lurtotecan	CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C(CN4CCN(C)CC4)C4=CC5=C(OCCO5)C=C4N=C13)C2=O	4956.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lurtotecan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lurtotecan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Lurtotecan 10V, Positive-QTOF	splash10-014i-0000090000-7256ee425864a7dc3710	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lurtotecan 20V, Positive-QTOF	splash10-014i-0000490000-dbfb85624f56dd9c0c25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lurtotecan 40V, Positive-QTOF	splash10-02t9-0000900000-204545251d8b0b5d8c40	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lurtotecan 10V, Negative-QTOF	splash10-00di-0000910000-633757a2b9ecd0515de6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lurtotecan 20V, Negative-QTOF	splash10-00di-0000900000-894f53c546d842e75bda	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lurtotecan 40V, Negative-QTOF	splash10-014i-0000900000-a473c17f488989093634	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

19099693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lurtotecan

METLIN ID

Not Available

PubChem Compound

23392970

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 Lurtotecan (HMDB0254221)

MOL for HMDB0254221 (Lurtotecan)

3D MOL for HMDB0254221 (Lurtotecan)

3D SDF for HMDB0254221 (Lurtotecan)

3D-SDF for HMDB0254221 (Lurtotecan)

PDB for HMDB0254221 (Lurtotecan)

3D PDB for HMDB0254221 (Lurtotecan)

SMILES for HMDB0254221 (Lurtotecan)

INCHI for HMDB0254221 (Lurtotecan)

Structure for HMDB0254221 (Lurtotecan)

3D Structure for HMDB0254221 (Lurtotecan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra