(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dienyl)phenyl butyrate

ID: ALA1946500

PubChem CID: 57382414

Max Phase: Preclinical

Molecular Formula: C22H30O2

Molecular Weight: 326.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@@](C)(/C=C/c1ccc(OC(=O)CCC)cc1)CCC=C(C)C

Standard InChI:  InChI=1S/C22H30O2/c1-6-9-21(23)24-20-13-11-19(12-14-20)15-17-22(5,7-2)16-8-10-18(3)4/h7,10-15,17H,2,6,8-9,16H2,1,3-5H3/b17-15+/t22-/m1/s1

Standard InChI Key:  AUPFDLBOQGWFJU-XEPMYJLFSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   22.4944    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4932    0.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2081    0.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9245    0.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9216    1.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2063    2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7784    0.3732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6346    2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3506    1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0635    2.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7795    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7826    0.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0697    0.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0728   -0.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3599   -0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7888   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6458    2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4893    2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3142    2.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0643    0.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3495    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0650    1.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6354    0.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9206    0.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  2  7  1  0
 14 15  1  0
  3  4  2  0
 14 16  1  0
  5  8  1  0
 10 17  1  0
 10 18  1  6
  8  9  2  0
 18 19  2  0
  4  5  1  0
  7 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 10 11  1  0
 21 23  1  0
  5  6  2  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946500

   [4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenyl] butanoate

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: 326.48

Molecular Weight (Monoisotopic): 326.2246

AlogP: 6.34

#Rotatable Bonds: 9

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.68

CX LogD: 6.68

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.30

Np Likeness Score: 1.23

References

1. Majeed R, Reddy MV, Chinthakindi PK, Sangwan PL, Hamid A, Chashoo G, Saxena AK, Koul S..  (2012)  Bakuchiol derivatives as novel and potent cytotoxic agents: a report.,  49  [PMID:22245048] [10.1016/j.ejmech.2011.12.018]

Source

Source(1):

• Scientific Literature