7-Ethyl-10-hydroxycamptothecin - Moligand™, ≥98% , CAS No.86639-52-3

CAS: 86639-52-3 Cat. No.: E110128 Molecular Weight: 392.4 EC Number: 643-093-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

UNII-0H43101T0J | BCP9000200 | 0H43101T0J | BP-24513 | CAMPTOTHECIN, 7-ETHYL-10-HYDROXY- | SN 38 lactone | AC-1357 | NCGC00167831-05 | Q-200299 | (S)-4,11-Diethyl-4,9-di-OH-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione | GTPL6925 | 1H-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

UNII-0H43101T0J | BCP9000200 | 0H43101T0J | BP-24513 | CAMPTOTHECIN, 7-ETHYL-10-HYDROXY- | SN 38 lactone | AC-1357 | NCGC00167831-05 | Q-200299 | (S)-4, 11-Diethyl-4, 9-di-OH-1, 12-dihydro-4H-2-oxa-6, 12a-diaza-dibenzo[b, h]fluorene-3, 13-dione | GTPL6925 | 1H-

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Active metabolite of irinotecan. Inhibitor of topoisomerase I.. Gene expression analysis of colon cancer cell lines treated with SN-38 showed differential effects: the majority of affected genes were down-regulated (including, most strongly, genes related

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488187375
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187375
• Canonical Smiles: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)O
• IUPAC Name: (19S)-10,19-diethyl-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
• InChIKey: FJHBVJOVLFPMQE-QFIPXVFZSA-N
• INCHI: 1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)O
• WGK Germany: 3
• RTECS: UQ0491000
• Alternate CAS: 86639-52-3
• NSC Number: 673596
• MeSH Entry Terms: 7 Ethyl 10 hydroxycamptothecin;7-ethyl-10-hydroxycamptothecin;Camptosar;Camptothecin 11;camptothecin-11;CPT 11;CPT-11;CPT11;irinotecan;irinotecan hydrochloride;Irrinotecan;NK012 compound;SN 38;SN 38 11;SN-38;SN-38-11;SN3811
• Molecular Weight: 392.4
• Reaxy-Rn: 4279374
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4279374&ln=

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: Hydroxyquinolines Pyranopyridines Pyridinones 1-hydroxy-2-unsubstituted benzenoids Tertiary alcohols Heteroaromatic compounds Carboxylic acid esters Lactams Lactones Azacyclic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Organonitrogen compounds Hydrocarbon derivatives Organopnictogen compounds Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Hydroxyquinoline - Pyranopyridine - Quinoline - 1-hydroxy-2-unsubstituted benzenoid - Pyridinone - Pyridine - Benzenoid - Heteroaromatic compound - Tertiary alcohol - Carboxylic acid ester - Lactam - Lactone - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Organic nitrogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - 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: pyranoindolizinoquinoline

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 1 (0 Activities)

Discover Target: TOP1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ABCG2 Tchem ATP-binding cassette sub-family G member 2 (0 Activities)

Discover Target: ABCG2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Specific Rotation[α]: +20.0 to +30.0 deg(C=0.2, THF)
• Melt Point(°C): 217°C
• Molecular Weight: 392.400 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 392.137 Da
• Monoisotopic Mass: 392.137 Da
• Topological Polar Surface Area: 100.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 820.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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