4-({[bis(2-chloroethyl)amino][(1-methyl-2-nitro-1H-imidazol-5-yl)methoxy]phosphoryl}amino)-N-benzyl-N-ethyl-N-methylbutane-1-aminium iodide

ID: ALA4284207

PubChem CID: 145992157

Max Phase: Preclinical

Molecular Formula: C23H38Cl2IN6O4P

Molecular Weight: 564.48

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC[N+](C)(CCCCNP(=O)(OCc1cnc([N+](=O)[O-])n1C)N(CCCl)CCCl)Cc1ccccc1.[I-]

Standard InChI:  InChI=1S/C23H38Cl2N6O4P.HI/c1-4-31(3,19-21-10-6-5-7-11-21)17-9-8-14-27-36(34,29(15-12-24)16-13-25)35-20-22-18-26-23(28(22)2)30(32)33;/h5-7,10-11,18H,4,8-9,12-17,19-20H2,1-3H3,(H,27,34);1H/q+1;/p-1

Standard InChI Key:  FNXUUEIHAHEZAA-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

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   17.4912  -21.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854  -20.8920    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.3751  -20.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5579  -20.1573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   13.9664  -21.4149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6039  -21.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3965  -20.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7813  -21.7092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0715  -22.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.9066  -21.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6148  -20.8946    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.4902  -22.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1974  -22.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0674  -22.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3577  -23.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1965  -23.3445    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.3535  -24.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6438  -24.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6396  -25.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9381  -24.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8120  -25.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.2290  -25.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0
  4  5  1  0
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  7  9  1  0
  6 10  1  0
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 10 12  2  0
  8 13  1  0
 13 14  1  0
 14  3  1  0
  3 15  2  0
  3 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
  2 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
 22 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
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 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
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M  CHG  4   1  -1  10   1  11  -1  27   1
M  END

Associated Targets(Human)

H-EMC-SS (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ACAN Aggrecan core protein (25 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 564.48Molecular Weight (Monoisotopic): 563.2064AlogP: 4.77#Rotatable Bonds: 18
Polar Surface Area: 102.53Molecular Species: NEUTRALHBA: 6HBD: 1
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 13.88CX Basic pKa: CX LogP: -0.90CX LogD: -0.90
Aromatic Rings: 2Heavy Atoms: 36QED Weighted: 0.07Np Likeness Score: -0.25

References

1. Ghedira D, Voissière A, Peyrode C, Kraiem J, Gerard Y, Maubert E, Vivier M, Miot-Noirault E, Chezal JM, Farhat F, Weber V..  (2018)  Structure-activity relationship study of hypoxia-activated prodrugs for proteoglycan-targeted chemotherapy in chondrosarcoma.,  158  [PMID:30199705] [10.1016/j.ejmech.2018.08.060]

Source