4-[(E)-2-((R)-2-Ethyl-1-oxo-thiochroman-6-yl)-propenyl]-benzoic acid ethyl ester

ID: ALA334025

PubChem CID: 44345781

Max Phase: Preclinical

Molecular Formula: C23H26O3S

Molecular Weight: 382.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(/C=C(\C)c2ccc3c(c2)CC[C@@H](CC)[S+]3[O-])cc1

Standard InChI:  InChI=1S/C23H26O3S/c1-4-21-12-10-20-15-19(11-13-22(20)27(21)25)16(3)14-17-6-8-18(9-7-17)23(24)26-5-2/h6-9,11,13-15,21H,4-5,10,12H2,1-3H3/b16-14+/t21-,27?/m1/s1

Standard InChI Key:  SLROQSVDLXPWMV-ZKUWKYKQSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.4209   -2.9854    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1325   -3.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3013   -4.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0154   -4.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5812   -4.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8957   -5.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148   -2.1551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8588   -4.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6943   -3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1756   -5.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -3.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -4.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8934   -6.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005   -4.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7355   -4.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4491   -5.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1695   -4.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6098   -5.4610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4494   -4.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7330   -5.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2990   -5.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -2.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3299   -5.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2602   -3.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0480   -5.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  6  1  0
  5  4  2  0
  6 13  1  0
  7 12  1  0
  8  1  1  0
  9  3  1  0
 10  2  1  0
 11  1  1  0
 12 18  1  0
 13 10  2  0
 14 16  1  0
 15  7  2  0
 16 11  1  0
 17  5  1  0
 18 22  2  0
 19 21  1  0
 20  7  1  0
 21 17  2  0
 22 17  1  0
 23  4  1  0
 11 24  1  1
 25 20  1  0
 26 24  1  0
 27 25  1  0
 14  3  1  0
  9  6  2  0
 12 19  2  0
M  CHG  2   1   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA334025

   ethyl 4-[(E)-2-[(2R)-2-ethyl-1-oxo-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: 382.53

Molecular Weight (Monoisotopic): 382.1603

AlogP: 5.26

#Rotatable Bonds: 5

Polar Surface Area: 49.36

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.43

CX LogD: 5.43

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -0.03

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]

Source

Source(1):

• Scientific Literature