7-(4,4-Dimethyl-thiochroman-6-yl)-3-methyl-octa-2,4,6-trienoic acid

ID: ALA34292

Cas Number: 108695-20-1

PubChem CID: 6447986

Max Phase: Preclinical

Molecular Formula: C20H24O2S

Molecular Weight: 328.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(/C=C/C=C(\C)c1ccc2c(c1)C(C)(C)CCS2)=C\C(=O)O

Standard InChI:  InChI=1S/C20H24O2S/c1-14(12-19(21)22)6-5-7-15(2)16-8-9-18-17(13-16)20(3,4)10-11-23-18/h5-9,12-13H,10-11H2,1-4H3,(H,21,22)/b6-5+,14-12+,15-7+

Standard InChI Key:  GAFLQIREHJATJD-ZFWGQPRBSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    0.4000   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -2.2667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  1  2  0
  6  3  1  0
  7 11  2  0
  8  7  1  0
  9  5  1  0
 10 12  1  0
 11 13  1  0
 12  6  2  0
 13 10  2  0
 14 16  2  0
 15  8  2  0
 16  5  1  0
 17  8  1  0
 18  9  1  0
 19  4  1  0
 20  4  1  0
 21  4  1  0
 22  6  1  0
 23 11  1  0
 18 19  1  0
 14  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA34292

   (2E,4E,6E)-3,7-Dimethyl-7-(tetrahydro-4,4-dimethylthiochroman-6-yl)-2,4,6-heptatrienoic acid

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: 328.48

Molecular Weight (Monoisotopic): 328.1497

AlogP: 5.45

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.47

CX Basic pKa: ┄

CX LogP: 5.33

CX LogD: 2.50

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 0.99

References

1. Spruce LW, Rajadhyaksha SN, Berlin KD, Gale JB, Miranda ET, Ford WT, Blossey EC, Verma AK, Hossain MB, van der Helm D..  (1987)  Heteroarotinoids. Synthesis, characterization, and biological activity in terms of an assessment of these systems to inhibit the induction of ornithine decarboxylase activity and to induce terminal differentiation of HL-60 cells.,  30  (8): [PMID:3612691] [10.1021/jm00391a033]

2. 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]

3. Benbrook DM, Subramanian S, Gale JB, Liu S, Brown CW, Boehm MF, Berlin KD..  (1998)  Synthesis and characterization of heteroarotinoids demonstrate structure specificity relationships.,  41  (19): [PMID:9733501] [10.1021/jm980308p]

4. Spruce LW, Gale JB, Berlin KD, Verma AK, Breitman TR, Ji XH, van der Helm D..  (1991)  Novel heteroarotinoids: synthesis and biological activity.,  34  (1): [PMID:1992144] [10.1021/jm00105a065]

5. 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