5-epi-icetexone

ID: ALA5280087

Max Phase: Preclinical

Molecular Formula: C20H22O5

Molecular Weight: 342.39

Names and Identifiers

Canonical SMILES:  CC(C)C1=C(O)C(=O)C2=C(C=C[C@H]3[C@]4(CCC[C@]3(C)C(=O)O4)C2)C1=O

Standard InChI:  InChI=1S/C20H22O5/c1-10(2)14-15(21)11-5-6-13-19(3)7-4-8-20(13,25-18(19)24)9-12(11)16(22)17(14)23/h5-6,10,13,23H,4,7-9H2,1-3H3/t13-,19+,20+/m1/s1

Standard InChI Key:  NFLLWTNAXDSKKC-CWVNLOTRSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -2.5709    0.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    0.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419    0.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565   -0.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709   -0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039    0.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3176   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880   -0.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659    1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951    1.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9624    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004   -0.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    2.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159   -0.8144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0105    2.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087   -0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212   -1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6415   -1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419    1.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087   -2.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.2923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 10  2  0
  4 11  1  0
  8 12  1  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
  9 15  1  0
 12 16  2  0
 15 17  2  0
 13 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
  5 22  1  0
  5 23  1  6
  3 24  1  1
 24 22  1  0
 22 25  2  0
  4 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5280087

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.39

Molecular Weight (Monoisotopic): 342.1467

AlogP: 2.96

#Rotatable Bonds: 1

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.87

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 1.60

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 2.63

References

1. Troncoso ME, Germanó MJ, Arrieta VJ, García Bustos MF, Cifuente D, Cargnelutti DE, Lozano ES..  (2023)  Antiparasitic Activity of Two Natural Terpenes from Salvia cuspidata against Leishmania amazonensis.,  86  (4): [PMID:36857574] [10.1021/acs.jnatprod.2c00976]

Source

Source(1):

• Scientific Literature