4-[(E)-2-(2-Octyl-thiochroman-6-yl)-propenyl]-benzoic acid ethyl ester

ID: ALA120980

PubChem CID: 10718405

Max Phase: Preclinical

Molecular Formula: C29H38O2S

Molecular Weight: 450.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCC1CCc2cc(/C(C)=C/c3ccc(C(=O)OCC)cc3)ccc2S1

Standard InChI:  InChI=1S/C29H38O2S/c1-4-6-7-8-9-10-11-27-18-16-26-21-25(17-19-28(26)32-27)22(3)20-23-12-14-24(15-13-23)29(30)31-5-2/h12-15,17,19-21,27H,4-11,16,18H2,1-3H3/b22-20+

Standard InChI Key:  AZQBNTMXFDQFCZ-LSDHQDQOSA-N

Molfile:  

     RDKit          2D

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   -2.9250   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  5  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA120980

   ethyl 4-[(E)-2-(2-octyl-3,4-dihydro-2H-thiochromen-6-yl)prop-1-enyl]benzoate

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: 450.69

Molecular Weight (Monoisotopic): 450.2593

AlogP: 8.58

#Rotatable Bonds: 11

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 9.48

CX LogD: 9.48

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: -0.06

References

1. Benbrook DM, Madler MM, Spruce LW, Birckbichler PJ, Nelson EC, Subramanian S, Weerasekare GM, Gale JB, Patterson MK, Wang B, Wang W, Lu S, Rowland TC, DiSivestro P, Lindamood C, Hill DL, Berlin KD..  (1997)  Biologically active heteroarotinoids exhibiting anticancer activity and decreased toxicity.,  40  (22): [PMID:9357524] [10.1021/jm970196m]

2. Zacheis D, Dhar A, Lu S, Madler MM, Klucik J, Brown CW, Liu S, Clement F, Subramanian S, Weerasekare GM, Berlin KD, Gold MA, Houck JR, Fountain KR, Benbrook DM..  (1999)  Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors.,  42  (21): [PMID:10543887] [10.1021/jm990292i]

Source

Source(1):

• Scientific Literature