(1R,2S,3S,4R,5R,6R,7S,9S)-4-(acetyloxy)-7-(benzoyloxy)-2,3-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl benzoate

ID: ALA2287533

PubChem CID: 15000187

Max Phase: Preclinical

Molecular Formula: C31H36O9

Molecular Weight: 552.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1[C@H](OC(=O)c2ccccc2)[C@@]2(C)[C@@H](OC(=O)c3ccccc3)C[C@H]3C[C@]2(OC3(C)C)[C@@](C)(O)[C@H]1O

Standard InChI:  InChI=1S/C31H36O9/c1-18(32)37-23-24(33)30(5,36)31-17-21(28(2,3)40-31)16-22(38-26(34)19-12-8-6-9-13-19)29(31,4)25(23)39-27(35)20-14-10-7-11-15-20/h6-15,21-25,33,36H,16-17H2,1-5H3/t21?,22-,23+,24-,25-,29+,30-,31+/m0/s1

Standard InChI Key:  RDXSWFVBIRMSGY-ZHBBPFAKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2287533

   [(1R,2S,3S,4R,5R,6R,7S,9S)-4-acetyloxy-5-benzoyloxy-2,3-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate

Molecule Features

Natural Product: Yes

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: 552.62

Molecular Weight (Monoisotopic): 552.2359

AlogP: 3.46

#Rotatable Bonds: 5

Polar Surface Area: 128.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.56

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.42

Np Likeness Score: 2.10

References

1. Gonzalez AG, Jimenez IA, Ravelo AG, Coll J, Gonzalez JA, Lloria J.  (1997)  Antifeedant activity of sesquiterpenes from celastraceae,  25  (6): [10.1016/S0305-1978(97)00035-5]

Source

Source(1):

• Scientific Literature