ContaminantDB: topotecan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 12:57:51 UTC

Update Date

2016-11-09 01:23:18 UTC

Accession Number

CHEM045233

Identification

Common Name

topotecan

Class

Small Molecule

Description

An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA topoisomerases, type I.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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 Molecular Mass

421.446 g/mol

Monoisotopic Mass

421.164 g/mol

CAS Registry Number

123948-87-8

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

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.86 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rw-0019000000-dd5f6ac57d5951105684	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0kmi-3001490000-ae90c2325c77269d874b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00b9-0019400000-11f24a2a9b88f6c67514	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-1009000000-b9244ee1f6cd61fee4f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0009000000-d66ee57d6e010d309c66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0006900000-89514722d3cccd3d4496	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00b9-0019300000-58bcf8842222fe631eca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1097000000-5b71ebf26d18a059bf0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0004900000-c6c85b983396e6199196	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-1009500000-740f8b3ec7e0bca5f75f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pwc-3029000000-65747933e72b20c9b71f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-0009500000-6c4802693f32d6eec744	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-258882d388fa7db50bff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05i3-4039100000-203d71abf98396934b86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009100000-c19a7f2e40a8ab89986a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-a6970c65760ce14af472	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01di-1029000000-30fc22abe375909eff46	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum