4,11-Bis[(2-guanidinoethyl)amino]anthra[2,3-b]furan-5,10-dione

ID: ALA3746814

Chembl Id: CHEMBL3746814

PubChem CID: 127042583

Max Phase: Preclinical

Molecular Formula: C22H24N8O3

Molecular Weight: 448.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCNc1c2c(c(NCCNC(=N)N)c3occc13)C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C22H24N8O3/c23-21(24)29-8-6-27-16-13-5-10-33-20(13)17(28-7-9-30-22(25)26)15-14(16)18(31)11-3-1-2-4-12(11)19(15)32/h1-5,10,27-28H,6-9H2,(H4,23,24,29)(H4,25,26,30)

Standard InChI Key:  DTZIWUDPGVXYEI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3746814

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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: 448.49

Molecular Weight (Monoisotopic): 448.1971

AlogP: 1.00

#Rotatable Bonds: 8

Polar Surface Area: 195.14

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 12.02

CX LogP: 1.06

CX LogD: -3.76

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.08

Np Likeness Score: 0.21

References

1. Tikhomirov AS, Shchekotikhin AE, Lee YH, Chen YA, Yeh CA, Tatarskiy VV, Dezhenkova LG, Glazunova VA, Balzarini J, Shtil AA, Preobrazhenskaya MN, Chueh PJ..  (2015)  Synthesis and Characterization of 4,11-Diaminoanthra[2,3-b]furan-5,10-diones: Tumor Cell Apoptosis through tNOX-Modulated NAD(+)/NADH Ratio and SIRT1.,  58  (24): [PMID:26633734] [10.1021/acs.jmedchem.5b00859]

2. Miglietta G, Cogoi S, Marinello J, Capranico G, Tikhomirov AS, Shchekotikhin A, Xodo LE..  (2017)  RNA G-Quadruplexes in Kirsten Ras (KRAS) Oncogene as Targets for Small Molecules Inhibiting Translation.,  60  (23): [PMID:29140695] [10.1021/acs.jmedchem.7b00622]

Source

Source(1):

• Scientific Literature