caprariolide A

ID: ALA520566

PubChem CID: 10634166

Max Phase: Preclinical

Molecular Formula: C15H18O3

Molecular Weight: 246.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC(c2ccoc2)=C[C@]2(C1)C[C@H](C)C(=O)O2

Standard InChI:  InChI=1S/C15H18O3/c1-10-5-13(12-3-4-17-9-12)8-15(6-10)7-11(2)14(16)18-15/h3-4,8-11H,5-7H2,1-2H3/t10-,11+,15+/m1/s1

Standard InChI Key:  YDUFVPKWFQXSAZ-ZETOZRRWSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   -2.9562   -1.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312   -1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8762   -0.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437   -0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110   -0.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6427   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6427   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283   -1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281    1.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5175    2.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    2.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5962    1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463   -2.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3573   -1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0916   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  5  1  0
  5  9  1  6
  9 10  2  0
 11 12  2  0
  5  1  1  0
  6  7  1  0
  1  2  1  0
  2  3  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
 10 11  1  0
  3  4  1  0
  2 16  2  0
  4  5  1  0
  7 17  1  6
  6 10  1  0
  3 18  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA520566

   CAPRARIOLIDE A

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: 246.31

Molecular Weight (Monoisotopic): 246.1256

AlogP: 3.41

#Rotatable Bonds: 1

Polar Surface Area: 39.44

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.71

Np Likeness Score: 2.10

References

1. Collins DO, Gallimore WA, Reynolds WF, Williams LA, Reese PB..  (2000)  New skeletal sesquiterpenoids, caprariolides A-D, from Capraria biflora and their insecticidal activity.,  63  (11): [PMID:11087595] [10.1021/np000280w]

Source

Source(1):

• Scientific Literature