(E)-3'-acetoxyartemidin

ID: ALA505861

PubChem CID: 21580110

Max Phase: Preclinical

Molecular Formula: C15H14O4

Molecular Weight: 258.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (E)-3'-Acetoxyartemidin | (E)-3'-acetoxyartemidin|CHEMBL505861|(e)-3-(3-acetyloxy-1-butenyl)-1h-2-benzopyran-1-one

Canonical SMILES:  CC(=O)OC(C)/C=C/c1cc2ccccc2c(=O)o1

Standard InChI:  InChI=1S/C15H14O4/c1-10(18-11(2)16)7-8-13-9-12-5-3-4-6-14(12)15(17)19-13/h3-10H,1-2H3/b8-7+

Standard InChI Key:  ZEOUYLGCBSJYCV-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -4.6264  -17.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6276  -17.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128  -18.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9146  -16.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1992  -17.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004  -17.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835  -18.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7608  -17.8398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596  -17.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811  -16.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858  -19.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442  -16.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307  -17.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848  -16.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982  -17.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868  -15.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1023  -15.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043  -14.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157  -15.7780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  5  6  1  0
  7 11  2  0
  9 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 14 16  1  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA505861

   (E)-3'-acetoxyartemidin

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: 258.27

Molecular Weight (Monoisotopic): 258.0892

AlogP: 2.76

#Rotatable Bonds: 3

Polar Surface Area: 56.51

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.79

Np Likeness Score: 1.21

References

1. Engelmeier D, Hadacek F, Hofer O, Lutz-Kutschera G, Nagl M, Wurz G, Greger H..  (2004)  Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.,  67  (1): [PMID:14738379] [10.1021/np0301339]

Source

Source(1):

• Scientific Literature