Frutescone O

ID: ALA4217519

PubChem CID: 145973556

Max Phase: Preclinical

Molecular Formula: C24H36O3

Molecular Weight: 372.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(C)C2=C(C(=O)C1(C)C)[C@@H](C(C)C)C[C@]1(CC[C@@]3(C(C)C)C[C@@H]13)O2

Standard InChI:  InChI=1S/C24H36O3/c1-13(2)16-11-24(10-9-23(14(3)4)12-17(23)24)27-19-15(5)21(26-8)22(6,7)20(25)18(16)19/h13-14,16-17H,9-12H2,1-8H3/t16-,17-,23+,24+/m1/s1

Standard InChI Key:  GANQKRZEIAHQPL-PYMOVNHWSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   29.8864  -19.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3031  -18.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4776  -18.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1494  -17.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0115  -17.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3031  -17.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0152  -19.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7273  -17.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7238  -18.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4327  -19.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1495  -18.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4396  -17.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5874  -17.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0161  -19.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4280  -19.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7112  -20.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1401  -20.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8740  -17.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1057  -17.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8729  -16.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0097  -16.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3934  -17.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9466  -18.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7691  -18.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9410  -18.9103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   35.1036  -16.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8218  -17.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0964  -16.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 23  1  0
 22 20  1  0
  4 19  1  1
  6  2  1  0
  6  5  2  0
  2  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11  4  1  0
  4 12  1  0
  6 13  1  0
  7 14  2  0
 10 15  1  6
 15 16  1  0
 15 17  1  0
 13 18  1  0
 20 19  1  0
  5 21  1  0
 23 22  1  0
 24 23  1  0
 22 24  1  0
 23 25  1  6
 22 26  1  6
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217519

   ---

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: 372.55

Molecular Weight (Monoisotopic): 372.2664

AlogP: 5.66

#Rotatable Bonds: 3

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 2.36

References

1. Hou JQ, Guo C, Zhao JJ, Dong YY, Hu XL, He QW, Zhang BB, Yan M, Wang H..  (2017)  Anti-inflammatory Meroterpenoids from Baeckea frutescens.,  80  (8): [PMID:28753309] [10.1021/acs.jnatprod.7b00042]

Source

Source(1):

• Scientific Literature