rac-(E/Z)-(4-(2-ethylhexylidene)-2-(hydroxymethyl)-5-oxo-tetrahydrofuran-2-yl)methyl 4-nitrobenzoate

ID: ALA472526

Chembl Id: CHEMBL472526

PubChem CID: 25052841

Max Phase: Preclinical

Molecular Formula: C21H27NO7

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(/C=C1/CC(CO)(COC(=O)c2ccc([N+](=O)[O-])cc2)OC1=O)CC

Standard InChI:  InChI=1S/C21H27NO7/c1-3-5-6-15(4-2)11-17-12-21(13-23,29-20(17)25)14-28-19(24)16-7-9-18(10-8-16)22(26)27/h7-11,15,23H,3-6,12-14H2,1-2H3/b17-11-

Standard InChI Key:  VVJHXKZXFGSSSC-BOPFTXTBSA-N

Alternative Forms

1. Parent:

   

   ALA472526

   rac-(Z)-[4-(2-Ethylhexylidene)-2-(hydroxymethyl)-5-oxo-2-2,3-dihydrofuryl]methyl4-nitrobenzoate

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: 405.45

Molecular Weight (Monoisotopic): 405.1788

AlogP: 3.57

#Rotatable Bonds: 10

Polar Surface Area: 115.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.27

Np Likeness Score: 0.79

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