methyl 17-((2R,3R,4S,5S,6R)-6-(acetoxymethyl)-3-((2S,3R,4S,5S,6R)-6-(acetoxymethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yloxy)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)octadec-9-enoate

ID: ALA5207323

PubChem CID: 10818633

Max Phase: Preclinical

Molecular Formula: C35H60O15

Molecular Weight: 720.85

Names and Identifiers

Canonical SMILES:  COC(=O)CCCCCCC/C=C\CCCCCCC(C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C35H60O15/c1-22(18-16-14-12-10-8-6-5-7-9-11-13-15-17-19-27(38)44-4)47-35-33(31(42)29(40)26(49-35)21-46-24(3)37)50-34-32(43)30(41)28(39)25(48-34)20-45-23(2)36/h5-6,22,25-26,28-35,39-43H,7-21H2,1-4H3/b6-5-/t22?,25-,26-,28-,29-,30+,31+,32-,33-,34+,35-/m1/s1

Standard InChI Key:  FLECYNVBJPYOEP-HVZMVQHPSA-N

Molfile:  

 
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Alternative Forms

1. Parent:

   

   ALA5207323

   methyl (Z)-17-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyoctadec-9-enoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 720.85

Molecular Weight (Monoisotopic): 720.3932

AlogP: 1.96

#Rotatable Bonds: 23

Polar Surface Area: 216.97

Molecular Species: NEUTRAL

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.09

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: ┄

Heavy Atoms: 50

QED Weighted: 0.04

Np Likeness Score: 1.38

References

1. Miceli RT, Corr DT, Barroso M, Dogra N, Gross RA..  (2022)  Sophorolipids: Anti-cancer activities and mechanisms.,  65  [PMID:35526504] [10.1016/j.bmc.2022.116787]

Source

Source(1):

• Scientific Literature