(1S,2S,5S,6R,7R,8R,9R,12R)-6,12-bis(acetyloxy)-7-(benzoyloxy)-2-hydroxy-8-(4-methoxybutyl)-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl benzoate

ID: ALA2287538

PubChem CID: 76312939

Max Phase: Preclinical

Molecular Formula: C37H46O11

Molecular Weight: 666.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCCC[C@@H]1[C@@H]2[C@@H](OC(C)=O)[C@@]3(OC2(C)C)[C@@](OC(C)=O)([C@@H](OC(=O)c2ccccc2)CC[C@]3(C)O)[C@@H]1OC(=O)c1ccccc1

Standard InChI:  InChI=1S/C37H46O11/c1-23(38)44-31-29-27(19-13-14-22-43-6)30(46-33(41)26-17-11-8-12-18-26)36(47-24(2)39)28(45-32(40)25-15-9-7-10-16-25)20-21-35(5,42)37(31,36)48-34(29,3)4/h7-12,15-18,27-31,42H,13-14,19-22H2,1-6H3/t27-,28+,29-,30-,31-,35+,36-,37+/m1/s1

Standard InChI Key:  JHTXDDLQJDLFCM-MADCNHOOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2287538

   [(1S,2S,5S,6R,7R,8R,9R,12R)-6,12-diacetyloxy-7-benzoyloxy-2-hydroxy-8-(4-methoxybutyl)-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] benzoate

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: 666.76

Molecular Weight (Monoisotopic): 666.3040

AlogP: 4.83

#Rotatable Bonds: 11

Polar Surface Area: 143.89

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.68

CX Basic pKa: ┄

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.20

Np Likeness Score: 1.60

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