(2R,3R)-2-Hydroxymethyl-5-oxo-4-tridec-(E)-ylidene-tetrahydro-furan-3-carboxylic acid methyl ester

ID: ALA13306

Chembl Id: CHEMBL13306

PubChem CID: 44268453

Max Phase: Preclinical

Molecular Formula: C21H36O5

Molecular Weight: 368.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCC/C=C1/C(=O)O[C@@H](CO)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C21H36O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-20(25-17(2)23)19(16-22)26-21(18)24/h15,19-20,22H,3-14,16H2,1-2H3/b18-15+/t19-,20+/m0/s1

Standard InChI Key:  TWUWFRLZDWDJLT-MSLZVHJSSA-N

Alternative Forms

1. Parent:

   

   ALA13306

   (2R,3R)-2-Hydroxymethyl-5-oxo-4-tridec-(E)-ylidene-tetrahydro-furan-3-carboxylic acid methyl 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: 368.51

Molecular Weight (Monoisotopic): 368.2563

AlogP: 4.46

#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: 5.45

CX LogD: 5.45

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 1.70

References

1. Lee J, Marquez VE, Lewin NE, Bahador A, Kazanietz MG, Blumberg PM.  (1993)  Conformationally constrained analogues of diacylglycerol (DAG). 4. Interaction of -alkylidene--lactones with protein kinase C (PK-C),  3  (6): [10.1016/S0960-894X(00)80296-6]

2. 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]

Source

Source(1):

• Scientific Literature