caprariolide B

ID: ALA488191

PubChem CID: 10610434

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-HFAKWTLXSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    3.8636   -1.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6886   -1.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9436   -0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2761   -0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6088   -0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    0.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771   -0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8915   -1.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    0.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8915    0.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    1.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    2.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    2.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236    1.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735   -2.1753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -1.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -0.4684    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  1
M  END

Alternative Forms

1. Parent:

   

   ALA488191

   CAPRARIOLIDE B

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