Becatecarin - ≥98% , DNA topoisomerase II inhibitor, CAS No.119673-08-4, DNA topoisomerase II inhibitor

CAS: 119673-08-4 Cat. No.: B339160 Formula: C₃₃H₃₄Cl₂N₄O₇ Molecular Weight: 669.55

GRADE & PURITY ≥98%

Synonyms

BECATECARIN [MART.] | NSC 655649 | 1,11-DICHLORO-6-(2-(DIETHYLAMINO)ETHYL)-12,13-DIHYDRO-12-(4-O-METHYL-.BETA.-D-GLUCOPYRANOSYL)-5H-INDOLO(2,3-A)PYRROLO(3,4-C)CARBAZOLE-5,7(6H)-DIONE | DEAE-Rebeccamycin | Bms-181176 | KINETIN [WHO-DD] | 5H-INDOLO(2,3-A)PY

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Becatecarin is a semisynthetic water-soluble derivative of rebeccamycin. Becatecarin has been shown to be used as an antitumor antibiotic, a Topo II (topoisomerase II ) inhibitor and a DNA intercalating agent.

Specifications

Synonyms

BECATECARIN [MART.] | NSC 655649 | 1,11-DICHLORO-6-(2-(DIETHYLAMINO)ETHYL)-12,13-DIHYDRO-12-(4-O-METHYL-.BETA.-D-GLUCOPYRANOSYL)-5H-INDOLO(2,3-A)PYRROLO(3,4-C)CARBAZOLE-5,7(6H)-DIONE | DEAE-Rebeccamycin | Bms-181176 | KINETIN [WHO-DD] | 5H-INDOLO(2,3-A)PY

Specifications & Purity

≥98%

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.

Action Type

INHIBITOR

Mechanism of action

DNA topoisomerase II inhibitor

Purity

≥98%

Product Properties

pKa

pKa: 13.03 (Predicted), pKa: 9.78 (Predicted)

ALogP

3.6

Names and Identifiers

Canonical Smiles

CCN(CC)CCN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)NC3=C5C(=C2C1=O)C6=C(N5C7C(C(C(C(O7)CO)OC)O)O)C(=CC=C6)Cl

IUPAC Name

5,21-dichloro-13-[2-(diethylamino)ethyl]-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

InChIKey

JSKFWUPVIZYJMR-UDOAKELVSA-N

INCHI

1S/C33H34Cl2N4O7/c1-4-37(5-2)12-13-38-31(43)22-20-15-8-6-10-17(34)24(15)36-25(20)27-21(23(22)32(38)44)16-9-7-11-18(35)26(16)39(27)33-29(42)28(41)30(45-3)19(14-40)46-33/h6-11,19,28-30,33,36,40-42H,4-5,12-14H2,1-3H3/t19-,28-,29-,30-,33-/m1/s1

Isomeric SMILES

CCN(CC)CCN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)NC3=C5C(=C2C1=O)C6=C(N5[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)OC)O)O)C(=CC=C6)Cl

Molecular Weight

669.55

Reaxy-Rn

26173521

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26173521&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Carbazoles
        • Level5 Pyrrolocarbazoles
          • Level6 Indolocarbazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Carbazoles
• Intermediate Tree Nodes: Pyrrolocarbazoles
• Direct Parent: Indolocarbazoles
• Alternative Parents: Pyrrolo[2,3-a]carbazoles Pyrroloindoles Glycosylamines Isoindolones N-alkylindoles Indoles Isoindoles Substituted pyrroles Aryl chlorides Monosaccharides Oxanes Benzenoids Heteroaromatic compounds Lactams Secondary alcohols Trialkylamines Dialkyl ethers Azacyclic compounds Oxacyclic compounds Hydrocarbon derivatives Organic oxides Organochlorides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolocarbazole - Pyrrolo[2,3-a]carbazole - Pyrroloindole - Glycosyl compound - N-glycosyl compound - N-alkylindole - Isoindolone - Indole - Isoindole - Isoindole or derivatives - Aryl chloride - Aryl halide - Monosaccharide - Oxane - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Lactam - Dialkyl ether - Azacycle - Ether - Oxacycle - Primary alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organohalogen compound - Organochloride - Organonitrogen compound - Amine - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.
• 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

Chemical and Physical Properties

• Solubility: Soluble in water (pH-dependent), and DMSO.
• Refractive Index: n20D1.74 (Predicted)
• Boil Point(°C): 848.85° C at 760 mmHg (Predicted)
• Molecular Weight: 669.500 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 668.18 Da
• Monoisotopic Mass: 668.18 Da
• Topological Polar Surface Area: 140.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1150.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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