buddledin A

ID: ALA485981

Cas Number: 62346-20-7

PubChem CID: 5281514

Max Phase: Preclinical

Molecular Formula: C17H24O3

Molecular Weight: 276.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC/C=C(\C)C(=O)[C@H](OC(C)=O)[C@@H]2[C@@H]1CC2(C)C

Standard InChI:  InChI=1S/C17H24O3/c1-10-7-6-8-11(2)15(19)16(20-12(3)18)14-13(10)9-17(14,4)5/h8,13-14,16H,1,6-7,9H2,2-5H3/b11-8+/t13-,14+,16-/m1/s1

Standard InChI Key:  SXWKLEULMBLXJM-PCRFWOPQSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.2588   -0.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685    0.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4455   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -0.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415   -0.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477   -1.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -0.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786    1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -1.9751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648    0.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304    0.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7227    0.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620   -0.5405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4838   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2438   -1.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6814    0.5553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -0.6756    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  1  2  1  0
  1  4  1  0
 11  6  1  0
 12 13  1  0
 13 14  1  0
 14 11  1  0
  6  7  1  0
  6 15  1  6
  7  5  1  0
 15 16  1  0
  2  3  1  0
 16 17  1  0
  5  8  1  0
 16 18  2  0
  3 12  1  0
 14 19  1  0
  3  9  2  0
 14 20  1  0
  5  4  2  0
 11 21  1  6
  7 10  2  0
 12 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA485981

   BUDDLEDIN A

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: 276.38

Molecular Weight (Monoisotopic): 276.1725

AlogP: 3.45

#Rotatable Bonds: 1

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: 3.10

References

1. Mensah AY, Houghton PJ, Bloomfield S, Vlietinck A, Vanden Berghe D..  (2000)  Known and novel terpenes from Buddleja globosa displaying selective antifungal activity against dermatophytes.,  63  (9): [PMID:11000021] [10.1021/np0001023]

2. Liao YH, Houghton PJ, Hoult JR..  (1999)  Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation.,  62  (9): [PMID:10514305] [10.1021/np990092+]

3. Larsson J, Gottfries J, Bohlin L, Backlund A..  (2005)  Expanding the ChemGPS chemical space with natural products.,  68  (7): [PMID:16038536] [10.1021/np049655u]

Source

Source(1):

• Scientific Literature