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6-(2-Amino-ethyl)-2,3-dimethoxy-6H-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluorene-5,12-dione hydrochloride

ID: ALA187631

PubChem CID: 45027828

Max Phase: Preclinical

Molecular Formula: C21H19ClN2O6

Molecular Weight: 394.38

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc2c3c(n(CCN)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2.Cl

Standard InChI:  InChI=1S/C21H18N2O6.ClH/c1-26-14-5-10-13(8-15(14)27-2)21(25)23(4-3-22)19-11-6-16-17(29-9-28-16)7-12(11)20(24)18(10)19;/h5-8H,3-4,9,22H2,1-2H3;1H

Standard InChI Key:  HGKJLPYOQQNYSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.0542   -0.0917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9167    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -3.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    0.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    1.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458   -2.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458   -0.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -2.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  1  0
  5  9  1  0
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  8  3  1  0
  9  7  1  0
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 12 10  1  0
 13  7  2  0
 14  9  2  0
 15 12  2  0
 16 11  2  0
 17 18  2  0
 18 13  1  0
 19  5  2  0
 20  6  2  0
 21 16  1  0
 22 15  1  0
 23 22  1  0
 24  4  1  0
 25 17  1  0
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 30 26  1  0
 10  8  2  0
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 21 23  1  0
M  END

Associated Targets(Human)

HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-539 (44845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-62 (47335 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SN12C (47755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-435 (38290 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Panel (Carcinoma cell lines) (272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Panel NCI-60 (60 carcinoma cell lines) (1088 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 394.38Molecular Weight (Monoisotopic): 394.1165AlogP: 1.92#Rotatable Bonds: 4
Polar Surface Area: 102.01Molecular Species: BASEHBA: 8HBD: 1
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.79CX LogP: 0.63CX LogD: -0.77
Aromatic Rings: 3Heavy Atoms: 29QED Weighted: 0.56Np Likeness Score: 0.42

References

1. Nagarajan M, Xiao X, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2003)  Design, synthesis, and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine side chains on the lactam nitrogen.,  46  (26): [PMID:14667224] [10.1021/jm030313f]
2. Nagarajan M, Morrell A, Fort BC, Meckley MR, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings.,  47  (23): [PMID:15509164] [10.1021/jm040025z]
3. Morrell A, Jayaraman M, Nagarajan M, Fox BM, Meckley MR, Ioanoviciu A, Pommier Y, Antony S, Hollingshead M, Cushman M..  (2006)  Evaluation of indenoisoquinoline topoisomerase I inhibitors using a hollow fiber assay.,  16  (16): [PMID:16750365] [10.1016/j.bmcl.2006.05.048]

Source