1,5-bis(4-(tetrahydro-2H-pyran-3-yloxy)phenyl)penta-1,4-dien-3-one

ID: ALA1091226

PubChem CID: 46886164

Max Phase: Preclinical

Molecular Formula: C27H30O5

Molecular Weight: 434.53

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(OC2CCCOC2)cc1)/C=C/c1ccc(OC2CCCOC2)cc1

Standard InChI:  InChI=1S/C27H30O5/c28-23(11-5-21-7-13-24(14-8-21)31-26-3-1-17-29-19-26)12-6-22-9-15-25(16-10-22)32-27-4-2-18-30-20-27/h5-16,26-27H,1-4,17-20H2/b11-5+,12-6+

Standard InChI Key:  BSHWHFPFQYTGCO-YDWXAUTNSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   13.1469   -8.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4315   -7.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7178   -8.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0028   -7.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2896   -8.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2905   -8.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0107   -9.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7211   -8.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5773   -9.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5799  -10.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8652  -10.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8658  -11.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5797  -11.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947  -11.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2958  -10.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5732   -8.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8574   -7.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2870   -7.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0030   -8.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0039   -8.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7191   -9.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4330   -8.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4271   -8.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7114   -7.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1495   -9.3138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1538  -10.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4388  -10.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4410  -11.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1558  -11.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8699  -11.3686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8694  -10.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8547   -6.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  3  1  0
  1 17  1  0
 16 17  1  0
 16 18  2  0
  6  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
 10 11  1  0
 21 22  2  0
  2  3  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
  1  2  2  0
 22 25  1  0
  6  7  1  0
 25 26  1  0
 26 27  1  0
  3  4  2  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14 15  1  0
 17 32  2  0
M  END

Associated Targets(Human)

HSD17B3 Tchem Estradiol 17-beta-dehydrogenase 3 (821 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Hsd17b3 Testosterone 17-beta-dehydrogenase 3 (232 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: 434.53Molecular Weight (Monoisotopic): 434.2093AlogP: 5.10#Rotatable Bonds: 8
Polar Surface Area: 53.99Molecular Species: NEUTRALHBA: 5HBD:
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 5.35CX LogD: 5.35
Aromatic Rings: 2Heavy Atoms: 32QED Weighted: 0.54Np Likeness Score: 0.19

References

1. Hu GX, Liang G, Chu Y, Li X, Lian QQ, Lin H, He Y, Huang Y, Hardy DO, Ge RS..  (2010)  Curcumin derivatives inhibit testicular 17beta-hydroxysteroid dehydrogenase 3.,  20  (8): [PMID:20346654] [10.1016/j.bmcl.2010.02.089]

Source