rac-(E/Z)-(4-(3-(trifluoromethyl)benzylidene)-2-(hydroxymethyl)-5-oxo-tetrahydrofuran-2-yl)methyl 3,5,5-trimethylhexanoate

ID: ALA462377

Chembl Id: CHEMBL462377

PubChem CID: 44593435

Max Phase: Preclinical

Molecular Formula: C23H29F3O5

Molecular Weight: 442.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CC(=O)OCC1(CO)C/C(=C/c2cccc(C(F)(F)F)c2)C(=O)O1)CC(C)(C)C

Standard InChI:  InChI=1S/C23H29F3O5/c1-15(11-21(2,3)4)8-19(28)30-14-22(13-27)12-17(20(29)31-22)9-16-6-5-7-18(10-16)23(24,25)26/h5-7,9-10,15,27H,8,11-14H2,1-4H3/b17-9-

Standard InChI Key:  BXISOVMQIGEZCL-MFOYZWKCSA-N

Alternative Forms

1. Parent:

   

   ALA462377

   [(4Z)-2-(hydroxymethyl)-5-oxo-4-[[3-(trifluoromethyl)phenyl]methylidene]oxolan-2-yl]methyl 3,5,5-trimethylhexanoate

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: 442.47

Molecular Weight (Monoisotopic): 442.1967

AlogP: 4.77

#Rotatable Bonds: 7

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.27

CX LogD: 5.27

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 0.31

References

1. Duan D, Sigano DM, Kelley JA, Lai CC, Lewin NE, Kedei N, Peach ML, Lee J, Abeyweera TP, Rotenberg SA, Kim H, Kim YH, El Kazzouli S, Chung JU, Young HA, Young MR, Baker A, Colburn NH, Haimovitz-Friedman A, Truman JP, Parrish DA, Deschamps JR, Perry NA, Surawski RJ, Blumberg PM, Marquez VE..  (2008)  Conformationally constrained analogues of diacylglycerol. 29. Cells sort diacylglycerol-lactone chemical zip codes to produce diverse and selective biological activities.,  51  (17): [PMID:18698758] [10.1021/jm8001907]

2. Duan D, Sigano DM, Kelley JA, Lai CC, Lewin NE, Kedei N, Peach ML, Lee J, Abeyweera TP, Rotenberg SA, Kim H, Kim YH, El Kazzouli S, Chung JU, Young HA, Young MR, Baker A, Colburn NH, Haimovitz-Friedman A, Truman JP, Parrish DA, Deschamps JR, Perry NA, Surawski RJ, Blumberg PM, Marquez VE..  (2008)  Conformationally constrained analogues of diacylglycerol. 29. Cells sort diacylglycerol-lactone chemical zip codes to produce diverse and selective biological activities.,  51  (17): [PMID:18698758] [10.1021/jm8001907]

Source

Source(1):

• Scientific Literature