3-[(morpholinyl)-1-propyl]-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

ID: ALA216462

Cas Number: 915303-09-2

PubChem CID: 11533060

Product Number: I412147, Order Now?

Max Phase: Preclinical

Molecular Formula: C26H26N2O7

Molecular Weight: 478.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Indotecan | INDOTECAN|915303-09-2|NSC-724998|LMP-400|Indotecan(LMP400)|BTA69L5M8D|2,3-dimethoxy-6-(3-morpholinopropyl)-5H-[1,3]dioxolo[4',5':5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione|UNII-BTA69L5M8D|LMP400|NSC724998|CHEMBL216462|SCHEMBL7712572|DTXSID90238613|BCP34018|EX-A3020|Indotecan hydrochloride (LMP-400)|ZB1545|AKOS040741879|NSC-724998LMP-400|SB16793|AC-35734|HY-18351|MS-28890|CS-0007476|LMP400; LMP-400; LMP 400|Q27274872|15,16-dimethoxy-20-(3-morpholin-4-ylpropyl)-5,7-dioxa-20-azapentacShow More⌵

Canonical SMILES:  COc1cc2c3c(n(CCCN4CCOCC4)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2

Standard InChI:  InChI=1S/C26H26N2O7/c1-31-19-10-15-18(13-20(19)32-2)26(30)28(5-3-4-27-6-8-33-9-7-27)24-16-11-21-22(35-14-34-21)12-17(16)25(29)23(15)24/h10-13H,3-9,14H2,1-2H3

Standard InChI Key:  FMFIFGLHVOZDEL-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA216462

   Indotecan

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 478.50

Molecular Weight (Monoisotopic): 478.1740

AlogP: 2.68

#Rotatable Bonds: 6

Polar Surface Area: 88.46

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.10

CX LogP: 1.29

CX LogD: 1.26

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.42

Np Likeness Score: -0.14

References

1. Nagarajan M, Morrell A, Ioanoviciu A, Antony S, Kohlhagen G, Agama K, Hollingshead M, Pommier Y, Cushman M..  (2006)  Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles.,  49  (21): [PMID:17034134] [10.1021/jm060564z]

2. Cinelli MA, Morrell AE, Dexheimer TS, Agama K, Agrawal S, Pommier Y, Cushman M..  (2010)  The structure-activity relationships of A-ring-substituted aromathecin topoisomerase I inhibitors strongly support a camptothecin-like binding mode.,  18  (15): [PMID:20630766] [10.1016/j.bmc.2010.06.040]

3. Peterson KE, Cinelli MA, Morrell AE, Mehta A, Dexheimer TS, Agama K, Antony S, Pommier Y, Cushman M..  (2011)  Alcohol-, diol-, and carbohydrate-substituted indenoisoquinolines as topoisomerase I inhibitors: investigating the relationships involving stereochemistry, hydrogen bonding, and biological activity.,  54  (14): [PMID:21710981] [10.1021/jm101338z]

4. Cinelli MA, Reddy PV, Lv PC, Liang JH, Chen L, Agama K, Pommier Y, van Breemen RB, Cushman M..  (2012)  Identification, synthesis, and biological evaluation of metabolites of the experimental cancer treatment drugs indotecan (LMP400) and indimitecan (LMP776) and investigation of isomerically hydroxylated indenoisoquinoline analogues as topoisomerase I poisons.,  55  (24): [PMID:23215354] [10.1021/jm300519w]

5. Lv PC, Elsayed MS, Agama K, Marchand C, Pommier Y, Cushman M..  (2016)  Design, Synthesis, and Biological Evaluation of Potential Prodrugs Related to the Experimental Anticancer Agent Indotecan (LMP400).,  59  (10): [PMID:27097152] [10.1021/acs.jmedchem.6b00220]

6. Cushman M..  (2021)  Design and Synthesis of Indenoisoquinolines Targeting Topoisomerase I and Other Biological Macromolecules for Cancer Chemotherapy.,  64  (24.0): [PMID:34879200] [10.1021/acs.jmedchem.1c01491]

Source

Source(1):

• Scientific Literature