3-beta-methoxy-iso-secotanapartholide

ID: ALA1085173

PubChem CID: 46881370

Max Phase: Preclinical

Molecular Formula: C16H20O5

Molecular Weight: 292.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H](C2=C(C)[C@@H](OC)CC2=O)[C@@H]1CCC(C)=O

Standard InChI:  InChI=1S/C16H20O5/c1-8(17)5-6-11-9(2)16(19)21-15(11)14-10(3)13(20-4)7-12(14)18/h11,13,15H,2,5-7H2,1,3-4H3/t11-,13+,15+/m1/s1

Standard InChI Key:  YMBVLYVGHGDKHO-ZLDLUXBVSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -3.1597    1.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334    1.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    2.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4123    2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1944    2.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440    0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090   -0.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426   -0.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743   -0.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293    0.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -0.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -1.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    1.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968    1.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183    2.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    2.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  1
  6  7  1  0
  3  8  2  0
  1  9  1  0
 10  2  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 13 15  2  0
 12 16  2  0
 14 17  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085173

   (4R,5S)-5-[(3S)-3-methoxy-2-methyl-5-oxocyclopenten-1-yl]-3-methylidene-4-(3-oxobutyl)oxolan-2-one

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: 292.33

Molecular Weight (Monoisotopic): 292.1311

AlogP: 1.76

#Rotatable Bonds: 5

Polar Surface Area: 69.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.64

CX LogD: 1.64

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.57

Np Likeness Score: 2.50

References

1. Ghantous A, Nasser N, Saab I, Darwiche N, Saliba NA..  (2009)  Structure-activity relationship of seco-tanapartholides isolated from Achillea falcata for inhibition of HaCaT cell growth.,  44  (9): [PMID:19464086] [10.1016/j.ejmech.2009.04.029]

Source

Source(1):

• Scientific Literature