rac-(E)-{2-(Hydroxymethyl)-4-[(4-methoxyphenyl)methylene]-5-oxo-1-2,3-dihydrofuryl}methyl 4-methoxybenzoate

ID: ALA461754

Chembl Id: CHEMBL461754

PubChem CID: 25053469

Max Phase: Preclinical

Molecular Formula: C22H22O7

Molecular Weight: 398.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\CC(CO)(COC(=O)c3ccc(OC)cc3)OC2=O)cc1

Standard InChI:  InChI=1S/C22H22O7/c1-26-18-7-3-15(4-8-18)11-17-12-22(13-23,29-21(17)25)14-28-20(24)16-5-9-19(27-2)10-6-16/h3-11,23H,12-14H2,1-2H3/b17-11+

Standard InChI Key:  PQLKHTRGIRKEMK-GZTJUZNOSA-N

Alternative Forms

1. Parent:

   

   ALA461754

   rac-(E)-{2-(Hydroxymethyl)-4-[(4-methoxyphenyl)methylene]-5-oxo-1-2,3-dihydrofuryl}methyl 4-methoxybenzoate

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: 398.41

Molecular Weight (Monoisotopic): 398.1366

AlogP: 2.62

#Rotatable Bonds: 7

Polar Surface Area: 91.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: 0.62

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]

3. Ann J, Czikora A, Saini AS, Zhou X, Mitchell GA, Lewin NE, Peach ML, Blumberg PM, Lee J..  (2018)  α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands.,  61  (14): [PMID:29860841] [10.1021/acs.jmedchem.8b00661]

Source

Source(1):

• Scientific Literature