2-(5-(4-carbamimidoylphenyl)furan-2-yl)benzo[d]oxazole-5-carboximidamide

Names and Identifiers

Synonyms: DB828 | CHEMBL1650566|SCHEMBL14519311|DB828

Canonical SMILES: N=C(N)c1ccc(-c2ccc(-c3nc4cc(C(=N)N)ccc4o3)o2)cc1

Standard InChI: InChI=1S/C19H15N5O2/c20-17(21)11-3-1-10(2-4-11)14-7-8-16(25-14)19-24-13-9-12(18(22)23)5-6-15(13)26-19/h1-9H,(H3,20,21)(H3,22,23)

Standard InChI Key: QGSDZVBDALDXMK-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.3465  -21.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3452  -22.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0587  -22.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7785  -22.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754  -21.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0567  -20.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6296  -22.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9152  -22.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6284  -23.3804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4879  -20.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1566  -21.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8261  -20.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5736  -20.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7479  -20.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5358  -21.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6247  -22.1255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2900  -20.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8380  -21.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4249  -22.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8295  -23.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6468  -23.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0580  -22.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6511  -21.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0576  -23.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6427  -24.4355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8832  -23.7242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  2  7  1  0
 12 15  1  0
 15 16  2  0
  3  4  2  0
  7  8  2  0
 16 19  1  0
 18 17  1  0
 17 15  1  0
  7  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  5 10  1  0
 20 21  2  0
 10 11  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 23 18  1  0
  5  6  2  0
 21 24  1  0
  6  1  1  0
 24 25  1  0
  1  2  2  0
 24 26  2  0
M  END

Alternative Forms

Parent:

ALA1650566
2-[5-(4-Carbamimidoylphenyl)furan-2-yl]-1,3-benzoxazole-5-carboximidamide

Associated Targets(Human)

HOXA9 DNA binding site (122 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

K562 (73714 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Trypanosoma evansi (198 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 345.36	Molecular Weight (Monoisotopic): 345.1226	AlogP: 3.32	#Rotatable Bonds: 4
Polar Surface Area: 138.91	Molecular Species: BASE	HBA: 5	HBD: 4
#RO5 Violations: ┄	HBA (Lipinski): 7	HBD (Lipinski): 6	#RO5 Violations (Lipinski): 1
CX Acidic pKa: ┄	CX Basic pKa: 11.22	CX LogP: 1.81	CX LogD: -2.94
Aromatic Rings: 4	Heavy Atoms: 26	QED Weighted: 0.33	Np Likeness Score: -0.77

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R.. (2009) In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model., 53 (12): [PMID:19786604] [10.1128/aac.00422-09]
2. Depauw S, Lambert M, Jambon S, Paul A, Peixoto P, Nhili R, Marongiu L, Figeac M, Dassi C, Paul-Constant C, Billoré B, Kumar A, Farahat AA, Ismail MA, Mineva E, Sweat DP, Stephens CE, Boykin DW, Wilson WD, David-Cordonnier MH.. (2019) Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model., 62 (3.0): [PMID:30645099] [10.1021/acs.jmedchem.8b01448]

Source

Source(1):

Scientific Literature