8(9)alpha-epoxy-4alpha-hydroxyfusicocc-2,3-en-14-one

ID: ALA4570119

PubChem CID: 155564355

Max Phase: Preclinical

Molecular Formula: C20H30O3

Molecular Weight: 318.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1CC(=O)[C@@]2(C)/C=C3\C(CC[C@@]3(C)O)[C@]3(C)O[C@@H]3CC12

Standard InChI:  InChI=1S/C20H30O3/c1-11(2)12-8-16(21)18(3)10-15-13(6-7-19(15,4)22)20(5)17(23-20)9-14(12)18/h10-14,17,22H,6-9H2,1-5H3/b15-10+/t12-,13?,14?,17+,18-,19+,20-/m0/s1

Standard InChI Key:  VSKUPZOQXCZDAV-RDXCJNTISA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   34.7719   -4.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7760   -3.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7789   -2.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2985   -3.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5599   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5561   -2.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1371   -4.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5208   -2.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8112   -1.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5248   -3.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9528   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3211   -4.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1209   -4.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2467   -3.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5384   -4.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9744   -3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6602   -4.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0164   -2.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1276   -2.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9427   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5347   -1.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9508   -5.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0661   -4.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3432   -1.4982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  6  3  1  0
  3  4  1  0
  4  2  1  0
  2  5  1  0
  5  6  1  0
  6 19  1  0
  5  7  2  0
  7 11  1  0
 10  8  1  0
  8 20  1  0
 19  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 11 15  1  6
 14 16  1  6
 16 17  1  0
 16 18  1  0
 20 19  1  0
 12 22  2  0
  2 23  1  6
 19 21  1  0
 20 21  1  0
 20 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4570119

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 318.46

Molecular Weight (Monoisotopic): 318.2195

AlogP: 3.50

#Rotatable Bonds: 1

Polar Surface Area: 49.83

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 2.60

References

1. D'Ambola M, Fiengo L, Chini MG, Cotugno R, Bader A, Bifulco G, Braca A, De Tommasi N, Dal Piaz F..  (2019)  Fusicoccane Diterpenes from Hypoestes forsskaolii as Heat Shock Protein 90 (Hsp90) Modulators.,  82  (3): [PMID:30839211] [10.1021/acs.jnatprod.8b00924]

Source

Source(1):

• Scientific Literature