Octadec-9-enoic acid 1-hydroxymethyl-2-octadec-9-enoyloxy-ethyl ester (DIOLEIN)

ID: ALA57517

Chembl Id: CHEMBL57517

PubChem CID: 6505653

Max Phase: Preclinical

Molecular Formula: C39H72O5

Molecular Weight: 621.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC/C=C/CCCCCCCC

Standard InChI:  InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17+,20-18+/t37-/m0/s1

Standard InChI Key:  AFSHUZFNMVJNKX-BIJVAZSDSA-N

Alternative Forms

1. Parent:

   

   ALA57517

   DIOLEIN

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: 621.00

Molecular Weight (Monoisotopic): 620.5380

AlogP: 11.51

#Rotatable Bonds: 34

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 13.06

CX LogD: 13.06

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.04

Np Likeness Score: 0.71

References

1. Nacro K, Sigano DM, Yan S, Nicklaus MC, Pearce LL, Lewin NE, Garfield SH, Blumberg PM, Marquez VE..  (2001)  An optimized protein kinase C activating diacylglycerol combining high binding affinity (Ki) with reduced lipophilicity (log P).,  44  (12): [PMID:11384235] [10.1021/jm010052e]

2. Nacro K, Bienfait B, Lewin NE, Blumberg PM, Marquez VE..  (2000)  Diacylglycerols with lipophilically equivalent branched acyl chains display high affinity for protein kinase C (PK-C). A direct measure of the effect of constraining the glycerol backbone in DAG lactones.,  10  (7): [PMID:10762046] [10.1016/s0960-894x(00)00070-6]

Source

Source(1):

• Scientific Literature