Your company account is blocked and you cannot place orders. If you have questions, please contact your company administrator.

12-((1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)-7,13-dioxo-12,13-dihydro-7H-indolo[3,2-j]phenanthridine 5-oxide

ID: ALA5209290

PubChem CID: 168295514

Max Phase: Preclinical

Molecular Formula: C27H21N5O6

Molecular Weight: 511.49

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C1c2c[n+]([O-])c3ccccc3c2C(=O)c2c1c1ccccc1n2Cc1cn([C@@H]2C[C@H](O)[C@@H](CO)O2)nn1

Standard InChI:  InChI=1S/C27H21N5O6/c33-13-21-20(34)9-22(38-21)31-11-14(28-29-31)10-30-18-7-3-1-5-15(18)24-25(30)27(36)23-16-6-2-4-8-19(16)32(37)12-17(23)26(24)35/h1-8,11-12,20-22,33-34H,9-10,13H2/t20-,21+,22-/m0/s1

Standard InChI Key:  NOMNMLFGSPUVNX-BDTNDASRSA-N

Molfile:  

 
     RDKit          2D

 38 44  0  0  0  0  0  0  0  0999 V2000
    0.5041    1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    1.1354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    1.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3003    0.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147    1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147    2.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3003    2.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    2.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    2.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    3.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397    2.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6601    2.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    1.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9655    2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3010    2.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161    3.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    3.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108    4.0637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463    4.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903    3.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    3.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    0.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421   -1.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -1.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -0.9372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.2023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -2.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -3.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174   -3.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7606   -2.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7072   -4.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -4.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0874   -4.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  1  1  0
  3  4  1  0
  5  4  1  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
  5 10  2  0
 10  9  1  0
 11  3  2  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
  1 14  1  0
 14 13  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 20 19  1  0
 15 20  2  0
 20 21  1  0
 21 22  1  0
 13 23  1  0
 21 23  2  0
 12 24  2  0
  4 25  1  0
 25 26  1  0
 27 26  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 31 28  1  6
 32 31  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 31  1  0
 33 36  1  6
 34 37  1  1
 37 38  1  0
M  CHG  2  21   1  22  -1
M  END

Alternative Forms

  1. Parent:

    ALA5209290

    ---

Associated Targets(Human)

A-375 (9258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L02 (4864 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Calf thymus DNA (4845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Calculated Properties

Molecular Weight: 511.49Molecular Weight (Monoisotopic): 511.1492AlogP: 1.48#Rotatable Bonds: 4
Polar Surface Area: 146.41Molecular Species: NEUTRALHBA: 10HBD: 2
#RO5 Violations: 1HBA (Lipinski): 11HBD (Lipinski): 2#RO5 Violations (Lipinski): 2
CX Acidic pKa: 13.88CX Basic pKa: 2.10CX LogP: 1.19CX LogD: 1.19
Aromatic Rings: 5Heavy Atoms: 38QED Weighted: 0.27Np Likeness Score: 0.34

References

1. Yang X, Wang ZP, Xiang S, Wang D, Zhao Y, Luo D, Qiu Y, Huang C, Guo J, Dai Y, Zhang SL, He Y..  (2022)  Optimization of the Natural Product Calothrixin A to Discover Novel Dual Topoisomerase I and II Inhibitors with Improved Anticancer Activity.,  65  (11.0): [PMID:35612499] [10.1021/acs.jmedchem.2c00615]

Source