Gimatecan - Moligand™,≥95% , DNA topoisomerase I inhibitor, CAS No.292618-32-7, DNA topoisomerase I inhibitor

CAS: 292618-32-7 Cat. No.: G646499 Molecular Weight: 447.48 EC Number: 695-730-5 PubChem CID: 9577124

GRADE & PURITY Moligand™, ≥95%

Synonyms

1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-(O-(1,1-dimethylethyl)oxime), (C(E),4S)- | NSC-18169 | NCGC00253588-01 | 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carboxaldeh

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Gimatecan (ST1481) is a potent topoisomerase I inhibitor. Gimatecan is a bioavailable camptothecin analogue with antitumor activity

Specifications

Synonyms

1H-Pyrano(3', 4':6, 7)indolizino(1, 2-b)quinoline-11-carboxaldehyde, 4-ethyl-3, 4, 12, 14-tetrahydro-4-hydroxy-3, 14-dioxo-, 11-(O-(1, 1-dimethylethyl)oxime), (C(E), 4S)- | NSC-18169 | NCGC00253588-01 | 1H-Pyrano[3', 4':6, 7]indolizino[1, 2-b]quinoline-11-carboxaldeh

Specifications & Purity

Moligand™, ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA topoisomerase I inhibitor

Purity

≥95%

Product Properties

• ALogP: 2

Names and Identifiers

• Canonical Smiles: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC=CC=C5N=C4C3=C2)C=NOC(C)(C)C)O
• IUPAC Name: (19S)-19-ethyl-19-hydroxy-10-[(E)-(2-methylpropan-2-yl)oxyiminomethyl]-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• InChIKey: UIVFUQKYVFCEKJ-OPTOVBNMSA-N
• INCHI: 1S/C25H25N3O5/c1-5-25(31)18-10-20-21-16(12-28(20)22(29)17(18)13-32-23(25)30)15(11-26-33-24(2,3)4)14-8-6-7-9-19(14)27-21/h6-11,31H,5,12-13H2,1-4H3/b26-11+/t25-/m0/s1
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC=CC=C5N=C4C3=C2)/C=N/OC(C)(C)C)O
• Alternate CAS: 292618-32-7,292620-90-7
• PubChem CID: 9577124
• MeSH Entry Terms: 7-t-butoxyiminomethyl-camptothecin;7-t-butoxyiminomethylcamptothecin;Gimatecan;LBQ707;ST 1481;ST1481
• Molecular Weight: 447.48

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Camptothecins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Camptothecins
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Camptothecins
• Alternative Parents: Quinolines and derivatives Pyranopyridines Pyridinones Benzenoids Tertiary alcohols Heteroaromatic compounds Carboxylic acid esters Lactams Lactones Azacyclic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Organonitrogen compounds Organopnictogen compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Pyranopyridine - Quinoline - Pyridinone - Pyridine - Benzenoid - Heteroaromatic compound - Tertiary alcohol - Carboxylic acid ester - Lactam - Lactone - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Alcohol - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound 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).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TOP1 Tclin DNA topoisomerase I (7553 Activities)

Discover Target: TOP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-29 (80576 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 33.33 mg/mL (74.48 mM; ultrasonic and warming and adjust pH to 10 with NaOH and heat to 60°C)
• Molecular Weight: 447.500 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 447.179 Da
• Monoisotopic Mass: 447.179 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 948.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1