Erythro-5,6-bis(4-hydroxyphenyl)octyl Ethyl Thioether

ID: ALA2374449

PubChem CID: 44286285

Max Phase: Preclinical

Molecular Formula: C23H32O2S

Molecular Weight: 372.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSCCCCC(c1ccc(O)cc1)C(C)(CC)c1ccc(O)cc1

Standard InChI:  InChI=1S/C23H32O2S/c1-4-23(3,19-11-15-21(25)16-12-19)22(8-6-7-17-26-5-2)18-9-13-20(24)14-10-18/h9-16,22,24-25H,4-8,17H2,1-3H3

Standard InChI Key:  JCDRAYIOBFSNHU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    2.1186   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -3.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -3.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -3.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -4.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248   -0.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -4.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248   -1.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -4.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4054   -1.9248    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7061   -2.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311   -1.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -0.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -5.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1199   -2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910   -2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620   -2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -2.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8344   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  2  0
  6  3  1  0
  7  4  2  0
  8  4  1  0
  9 13  1  0
 10 12  1  0
 11  7  1  0
 12  6  2  0
 13  8  2  0
 14  5  1  0
 15 22  1  0
  1 16  1  0
  1 17  1  0
 18 10  1  0
 19  9  1  0
  2 20  1  0
 21 15  1  0
 22 25  1  0
 23 20  1  0
 24 16  1  0
 25 23  1  0
 26 21  1  0
 14 10  2  0
 11  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2374449

   4-[8-Ethylsulfanyl-3-(4-hydroxyphenyl)-3-methyloctan-4-yl]phenol

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: 372.57

Molecular Weight (Monoisotopic): 372.2123

AlogP: 6.47

#Rotatable Bonds: 10

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.90

CX Basic pKa: ┄

CX LogP: 7.01

CX LogD: 7.01

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -0.26

References

1. Köhle H, Krohn K, Leclercq G..  (1989)  Hexestrol-linked cytotoxic agents: synthesis and binding affinity for estrogen receptors.,  32  (7): [PMID:2544725] [10.1021/jm00127a023]

2. Toogood PL..  (2002)  Inhibition of protein-protein association by small molecules: approaches and progress.,  45  (8): [PMID:11931608] [10.1021/jm010468s]

3. Doshi JM, Tian D, Xing C..  (2006)  Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer.,  49  (26): [PMID:17181155] [10.1021/jm060968r]

4. Xing C, Wang L, Tang X, Sham YY..  (2007)  Development of selective inhibitors for anti-apoptotic Bcl-2 proteins from BHI-1.,  15  (5): [PMID:17227711] [10.1016/j.bmc.2006.12.020]

5. Das SG, Doshi JM, Tian D, Addo SN, Srinivasan B, Hermanson DL, Xing C..  (2009)  Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4h-chromene-3-carboxylate (sha 14-1) and its analogues.,  52  (19): [PMID:19743858] [10.1021/jm9005059]

6. MacDonald ML, Lamerdin J, Owens S, Keon BH, Bilter GK, Shang Z, Huang Z, Yu H, Dias J, Minami T, Michnick SW, Westwick JK..  (2006)  Identifying off-target effects and hidden phenotypes of drugs in human cells.,  2  (6): [PMID:16680159] [10.1038/nchembio790]

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays