Tetradecanoic acid (2S,3R)-2-hydroxymethyl-5-oxo-tetrahydro-furan-3-yl ester

ID: ALA276429

Chembl Id: CHEMBL276429

PubChem CID: 11359830

Max Phase: Preclinical

Molecular Formula: C19H34O5

Molecular Weight: 342.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC(=O)O[C@@H]1CC(=O)O[C@H]1CO

Standard InChI:  InChI=1S/C19H34O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-18(21)23-16-14-19(22)24-17(16)15-20/h16-17,20H,2-15H2,1H3/t16-,17+/m1/s1

Standard InChI Key:  ZAAPYHDKFLKBSV-SJORKVTESA-N

Alternative Forms

1. Parent:

   

   ALA276429

   Tetradecanoic acid 2-hydroxymethyl-5-oxo-tetrahydro-furan-3-yl ester

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: 342.48

Molecular Weight (Monoisotopic): 342.2406

AlogP: 3.91

#Rotatable Bonds: 14

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: 4.63

CX LogD: 4.63

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: 1.25

References

1. Lee J, Marquez VE, Lewin NE, Kazanietz MG, Bahador A, Blumberg PM.  (1993)  Conformationally constrained analogues of diacylglycerol (DAG). 3. Interaction of -alkyl--lactones with protein kinase C (PK-C),  3  (6): [10.1016/S0960-894X(00)80295-4]

2. Lee J, Sharma R, Teng K, Lewin NE, Blumberg PM, Marquez VE.  (1994)  Conformationally constrained analogues of dag .8. Changes in PK-C binding affinity produced by isosteric groups of the 3-O-acyl function in 2-deoxy-L-ribonolactones,  4  (11): [10.1016/S0960-894X(01)80364-4]

3. Sharma R, Marquez VE, Milne GW, Lewin NE, Blumberg PM.  (1993)  Conformationally constrained analogues of diacylglycerol. 5. 2,5-Dideoxy-3-O-tetradecanoyl-D-galactono-1,4-lactone: A superior homologue of 3-O-tetradecanoyl-2-deoxy-L-ribonolactone with PK-C binding affinity.,  3  (10): [10.1016/S0960-894X(01)81002-7]

4. Lee J, Lewin NE, Blumberg PM, Marquez VE.  (1994)  Conformationally constrained analogues of diacylglycerol. 9.1 the effect of side-chain orientation on the protein kinase C (PK-C) binding affinity of -lactones,  4  (20): [10.1016/S0960-894X(01)80399-1]

5. Marquez VE, Lee J, Sharma R, Teng K, Wang S, Lewin NE, Bahador A, Kazanietz MG, Blumberg PM.  (1994)  Conformationally constrained analogues of diacylglycerol. 6. Changes in PK-C binding affinity for 3-O-acyl-2-deoxy-L-ribonolactones bearing different acyl chains.,  4  (2): [10.1016/S0960-894X(01)80144-X]

6. Lee J, Marquez VE, Lewin NE, Blumberg PM.  (1994)  Conformationally constrained analogues of DAG.7. Interaction of a medium-size -lactone with protein kinase C (PK-C)_,  4  (4): [10.1016/S0960-894X(01)80151-7]

Source

Source(1):

• Scientific Literature