NP-MRD: Showing NP-Card for Topotecan hydrochloride (NP0137403)

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Record Information

Version

2.0

Created at

2022-05-30 16:51:28 UTC

Updated at

2022-05-30 16:51:29 UTC

NP-MRD ID

NP0137403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Topotecan hydrochloride

Description

Topotecan, also known as hycamtin or topotecan lactone, 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). Topotecan is a drug which is used for the treatment of advanced ovarian cancer in patients with disease that has recurred or progressed following therapy with platinum-based regimens. Also used as a second-line therapy for treatment-sensitive small cell lung cancer, as well as in combination with cisplatin for the treatment of stage iv-b, recurrent, or persistent cervical cancer not amenable to curative treatment with surgery and/or radiation therapy. Topotecan is a very strong basic compound (based on its pKa). Topotecan hydrochloride was first documented in 1996 (PMID: 8853931). A pyranoindolizinoquinoline used as an antineoplastic agent (PMID: 9122737) (PMID: 9885371) (PMID: 20574789) (PMID: 21255983).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1030
  Mrv0541 02231215112D          

 31 35  0  0  1  0            999 V2000
    5.5924    3.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341    1.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0526    3.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8154   -3.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712   -2.9335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3300    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5793    2.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6922    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5793    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    2.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1549    2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516    3.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165   -0.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0127   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8622   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -2.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5589    1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -2.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3957   -1.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -2.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -3.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478   -3.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 17  1  0  0  0  0
  7 15  2  0  0  0  0
  7 23  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 20  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  2  0  0  0  0
 18 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    5.4791    0.8616   -1.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3539   -0.5929   -1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322   -0.8523   -0.1290 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1241   -2.2576   -0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -0.3802    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5216   -1.0463    0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4570    0.8728    1.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3209    1.5260    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397    0.9418    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172   -0.1828    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -0.6845   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6349   -0.0505    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560    1.0467    1.1630 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    1.5537    1.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8973    2.5964    2.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915    1.4998    1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5638    0.5235    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9437    0.3471    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030   -0.6856   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073   -0.8293   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6828    0.1683    0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0951    0.1963    0.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3520    0.7950   -0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6348    1.1316    1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4347   -1.8730   -0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -2.1611   -1.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311   -2.7673   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -2.6065   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273   -1.5544   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2925   -1.4210   -0.5638 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -0.3982    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5396    1.2210   -1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    1.0162   -3.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    1.5268   -1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2942   -1.0890   -2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4717   -0.9978   -2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9149   -2.6861   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3577    2.6204    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3791    1.5483    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.5845   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604    1.4587    2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203    2.5200    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5558    1.0678    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4835    0.0222    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3103    1.2228    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881    0.5035   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2539    1.8931   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3834    0.4970   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8359    1.7828    1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3817    1.8127    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1052    0.6186    2.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5953   -1.8096   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -3.5911   -2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -3.2907   -1.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  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 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 29  2  0
 29 28  1  0
 28 27  2  0
 27 25  1  0
 25 26  1  0
 25 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 29 30  1  0
 30 31  2  0
 13 14  1  0
 14 15  2  0
 10  3  1  0
 31 12  1  0
 14  9  1  0
 31 17  1  0
 20 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 28 54  1  0
 27 53  1  0
 26 52  1  0
 21 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
M  END

1030
  Mrv0541 02231215112D          

 31 35  0  0  1  0            999 V2000
    5.5924    3.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341    1.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0526    3.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8154   -3.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712   -2.9335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3300    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5793    2.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6922    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5793    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    2.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1549    2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516    3.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165   -0.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0127   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8622   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -2.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5589    1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -2.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3957   -1.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -2.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -3.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478   -3.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 17  1  0  0  0  0
  7 15  2  0  0  0  0
  7 23  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 20  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  2  0  0  0  0
 18 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=C(C=CC(O)=C4CN(C)C)N=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1

> <INCHI_KEY>
UCFGDBYHRUNTLO-QHCPKHFHSA-N

> <FORMULA>
C23H23N3O5

> <MOLECULAR_WEIGHT>
421.4458

> <EXACT_MASS>
421.163770861

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.85931866430069

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
-0.35709507722102324

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.71625075471723

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.003999445526812

> <JCHEM_PKA_STRONGEST_BASIC>
9.826297371129254

> <JCHEM_POLAR_SURFACE_AREA>
103.19999999999999

> <JCHEM_REFRACTIVITY>
115.0161

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
topotecan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1030                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.439   7.466   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.570   3.718   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.414   5.050   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.165   7.429   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.122  -6.691   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.748   2.740   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.715  -0.803   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.613  -5.476   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      11.816   5.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.415   4.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.081   1.970   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.612   1.713   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.081   5.050   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.236   0.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.759   0.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.415   2.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.748   4.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.356   5.042   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.056   6.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.828   6.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.564  -1.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.490  -2.429   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.076  -2.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.790  -3.935   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.110   3.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.257  -4.077   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.072  -3.593   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.755  -5.287   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.407  -5.115   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.080  -5.618   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.503  -6.733   0.000  0.00  0.00           C+0
CONECT    1   19   20                                                       
CONECT    2    9                                                            
CONECT    3   17                                                            
CONECT    4   20                                                            
CONECT    5   28                                                            
CONECT    6   11   12   17                                                  
CONECT    7   15   23                                                       
CONECT    8   26   30   31                                                  
CONECT    9    2   10   18   20                                             
CONECT   10    9   13   16                                                  
CONECT   11    6   15   16                                                  
CONECT   12    6   14                                                       
CONECT   13   10   17   19                                                  
CONECT   14   12   15   21                                                  
CONECT   15    7   11   14                                                  
CONECT   16   10   11                                                       
CONECT   17    3    6   13                                                  
CONECT   18    9   25                                                       
CONECT   19    1   13                                                       
CONECT   20    1    4    9                                                  
CONECT   21   14   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23    7   22   27                                                  
CONECT   24   22   26   28                                                  
CONECT   25   18                                                            
CONECT   26    8   24                                                       
CONECT   27   23   29                                                       
CONECT   28    5   24   29                                                  
CONECT   29   27   28                                                       
CONECT   30    8                                                            
CONECT   31    8                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
9-[(Dimethylamino)methyl]-10-hydroxy-(4S)-camptothecin	ChEBI
Topotecane	ChEBI
Topotecanum	ChEBI
Hycamtin	Kegg
Topotecan lactone	HMDB
SK And F 104864 a	HMDB
SK And F-104864-a	HMDB
SK And F104864a	HMDB
Topotecan hydrochloride	HMDB
9-Dimethylaminomethyl-10-hydroxycamptothecin	HMDB
Nogitecan hydrochloride	HMDB
SmithKline beecham brand OF topotecan hydrochloride	HMDB
Hycamtamine	HMDB
Hydrochloride, nogitecan	HMDB
Topotecan monohydrochloride, (S)-isomer	HMDB
9 Dimethylaminomethyl 10 hydroxycamptothecin	HMDB
Hydrochloride, topotecan	HMDB

Chemical Formula

C₂₃H₂₃N₃O₅

Average Mass

421.4458 Da

Monoisotopic Mass

421.16377 Da

IUPAC Name

(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

Traditional Name

topotecan

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=C(C=CC(O)=C4CN(C)C)N=C13)C2=O

InChI Identifier

InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1

InChI Key

UCFGDBYHRUNTLO-QHCPKHFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Hydroxyquinoline
Pyranopyridine
Quinoline
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Aralkylamine
Benzenoid
Pyridine
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Tertiary amine
Lactone
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organopnictogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:63632 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.84	ALOGPS
logP	-0.36	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.02 m³·mol⁻¹	ChemAxon
Polarizability	44.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015164

DrugBank ID

DB01030

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54705

KEGG Compound ID

C11158

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Topotecan

METLIN ID

Not Available

PubChem Compound

60700

PDB ID

TTC

ChEBI ID

63632

Good Scents ID

Not Available

References

General References

Herben VM, ten Bokkel Huinink WW, Beijnen JH: Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996 Aug;31(2):85-102. doi: 10.2165/00003088-199631020-00001. [PubMed:8853931 ]
Dennis MJ, Beijnen JH, Grochow LB, van Warmerdam LJ: An overview of the clinical pharmacology of topotecan. Semin Oncol. 1997 Feb;24(1 Suppl 5):S5-12-S5-18. [PubMed:9122737 ]
Kollmannsberger C, Mross K, Jakob A, Kanz L, Bokemeyer C: Topotecan - A novel topoisomerase I inhibitor: pharmacology and clinical experience. Oncology. 1999;56(1):1-12. doi: 10.1159/000011923. [PubMed:9885371 ]
Serna DS, Bekaii-Saab T, Kraut EH: A phase I study of topotecan and gemcitabine in advanced solid tumors. Invest New Drugs. 2011 Dec;29(6):1390-4. doi: 10.1007/s10637-010-9480-9. Epub 2010 Jun 25. [PubMed:20574789 ]
Cheng Q, Du Y, Wu K, Chen J, Zhou Y: Electrochemical detection of anticancer drug topotecan using nano-acetylene black film. Colloids Surf B Biointerfaces. 2011 May 1;84(1):135-9. doi: 10.1016/j.colsurfb.2010.12.027. Epub 2010 Dec 29. [PubMed:21255983 ]

Showing NP-Card for Topotecan hydrochloride (NP0137403)

MOL for NP0137403 (Topotecan hydrochloride)

3D MOL for NP0137403 (Topotecan hydrochloride)

3D SDF for NP0137403 (Topotecan hydrochloride)

3D-SDF for NP0137403 (Topotecan hydrochloride)

PDB for NP0137403 (Topotecan hydrochloride)

3D PDB for NP0137403 (Topotecan hydrochloride)

SMILES for NP0137403 (Topotecan hydrochloride)

INCHI for NP0137403 (Topotecan hydrochloride)

Structure for NP0137403 (Topotecan hydrochloride)

3D Structure for NP0137403 (Topotecan hydrochloride)