4-Pregnen-21-ol-3,20-dione-21-(4-methylbenzenesufonate)

ID: ALA1093759

PubChem CID: 14282245

Max Phase: Preclinical

Molecular Formula: C28H36O5S

Molecular Weight: 484.66

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)OCC(=O)[C@H]2CC[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC[C@]23C)cc1

Standard InChI:  InChI=1S/C28H36O5S/c1-18-4-7-21(8-5-18)34(31,32)33-17-26(30)25-11-10-23-22-9-6-19-16-20(29)12-14-27(19,2)24(22)13-15-28(23,25)3/h4-5,7-8,16,22-25H,6,9-15,17H2,1-3H3/t22-,23-,24-,25+,27-,28-/m0/s1

Standard InChI Key:  ZQPLMASYQDRTTR-DLIGHSALSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   -4.6188  -10.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6188   -9.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071   -8.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071  -10.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1913  -10.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754  -10.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595  -10.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -9.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -8.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -9.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215   -8.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2635   -7.8894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -7.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -8.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -7.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -7.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -8.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -8.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1913   -9.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1913   -8.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -9.7917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -8.5542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -9.7917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337  -10.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2646   -6.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833   -6.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073   -6.4957    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307   -6.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -7.3205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -5.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484   -7.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2711   -7.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6758   -6.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -5.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -5.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5007   -6.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 12 15  1  0
  9 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 19  1  0
 19 20  1  0
  3 20  1  0
  5 20  1  0
 20 21  1  1
 19 22  1  6
  8 23  1  1
  9 24  1  6
  1 25  2  0
  1  2  1  0
 13 26  2  0
  2  3  1  0
 14 27  1  0
  1  4  1  0
 27 28  1  0
  4  5  2  0
 28 29  1  0
  5  6  1  0
 28 30  2  0
  6  7  1  0
 28 31  2  0
  7  8  1  0
 29 32  2  0
  8  9  1  0
 32 33  1  0
  9 10  1  0
 33 34  2  0
 10 11  1  0
 34 35  1  0
 11 12  1  0
 35 36  2  0
 36 29  1  0
 12 13  1  1
 34 37  1  0
M  END

Associated Targets(Human)

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 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: 484.66Molecular Weight (Monoisotopic): 484.2283AlogP: 5.42#Rotatable Bonds: 5
Polar Surface Area: 77.51Molecular Species: NEUTRALHBA: 5HBD:
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 5.90CX LogD: 5.90
Aromatic Rings: 1Heavy Atoms: 34QED Weighted: 0.52Np Likeness Score: 1.11

References

1. Dexheimer TS, Gediya LK, Stephen AG, Weidlich I, Antony S, Marchand C, Interthal H, Nicklaus M, Fisher RJ, Njar VC, Pommier Y..  (2009)  4-Pregnen-21-ol-3,20-dione-21-(4-bromobenzenesulfonate) (NSC 88915) and related novel steroid derivatives as tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors.,  52  (22): [PMID:19883083] [10.1021/jm901061s]

Source