3-O-acetoxyacetylswietenolide

ID: ALA2271734

PubChem CID: 76323383

Max Phase: Preclinical

Molecular Formula: C31H38O11

Molecular Weight: 586.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COC(=O)[C@@H]1[C@@H]2CC3=C4CC(=O)O[C@@H](c5ccoc5)[C@]4(C)CC[C@@H]3[C@@](C)(C2=O)[C@@H]([C@@H](O)C(=O)OC)C1(C)C

Standard InChI:  InChI=1S/C31H38O11/c1-29(2)22(27(36)41-14-21(33)38-5)17-11-16-18(31(4,25(17)35)24(29)23(34)28(37)39-6)7-9-30(3)19(16)12-20(32)42-26(30)15-8-10-40-13-15/h8,10,13,17-18,22-24,26,34H,7,9,11-12,14H2,1-6H3/t17-,18-,22-,23+,24-,26-,30+,31+/m0/s1

Standard InChI Key:  VOBOCFHHUZDQJC-KGMWFFOSSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2271734

   3-O-ACETOXYACETYLSWIETENOLIDE

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: 586.63

Molecular Weight (Monoisotopic): 586.2414

AlogP: 3.10

#Rotatable Bonds: 6

Polar Surface Area: 155.64

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.42

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.30

Np Likeness Score: 2.15

References

1. Fowles R, Mootoo B, Ramsewak R, Khan A, Ramsubhag A, Reynolds W, Nair M..  (2010)  Identification of new limonoids from Swietenia and their biological activity against insects.,  66  (12): [PMID:20799251] [10.1002/ps.2013]

Source

Source(1):

• Scientific Literature