3-O-benzoylswietenolide

ID: ALA2271730

PubChem CID: 76308828

Max Phase: Preclinical

Molecular Formula: C34H38O9

Molecular Weight: 590.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](C(=O)Oc2ccccc2)[C@@H]2CC3=C4CC(=O)O[C@@H](c5ccoc5)[C@]4(C)CC[C@@H]3[C@@]1(C)C2=O

Standard InChI:  InChI=1S/C34H38O9/c1-32(2)25(30(38)42-19-9-7-6-8-10-19)21-15-20-22(34(4,28(21)37)27(32)26(36)31(39)40-5)11-13-33(3)23(20)16-24(35)43-29(33)18-12-14-41-17-18/h6-10,12,14,17,21-22,25-27,29,36H,11,13,15-16H2,1-5H3/t21-,22-,25-,26+,27-,29-,33+,34+/m0/s1

Standard InChI Key:  MZKUHDIDXQWBSU-ZGIPAOCXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2271730

   3-O-BENZOYLSWIETENOLIDE

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: 590.67

Molecular Weight (Monoisotopic): 590.2516

AlogP: 4.99

#Rotatable Bonds: 5

Polar Surface Area: 129.34

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: ┄

CX LogP: 4.35

CX LogD: 4.35

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.29

Np Likeness Score: 2.05

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