8-hydroxy-3-methoxy-iso-seco-tanaparatholide

ID: ALA1085176

PubChem CID: 46881372

Max Phase: Preclinical

Molecular Formula: C16H20O6

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20O6/c1-7(17)5-10(18)14-9(3)16(20)22-15(14)13-8(2)12(21-4)6-11(13)19/h10,12,14-15,18H,3,5-6H2,1-2,4H3/t10-,12?,14-,15+/m0/s1

Standard InChI Key:  KRJJHEXPFIEQEN-UFBLJUAHSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.9886   -5.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8149   -5.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0699   -4.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3997   -4.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360   -4.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538   -4.5001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -5.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8565   -4.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -6.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2969   -6.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0394   -6.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7059   -7.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3741   -6.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2129   -6.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1598   -7.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7044   -8.2987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8341   -5.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5480   -6.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2611   -5.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9750   -6.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2568   -4.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8336   -4.9681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9735   -5.4144    0.0000 H   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  0
  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  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  1
 14 23  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1085176

   (4S,5S)-4-[(1S)-1-hydroxy-3-oxobutyl]-5-(3-methoxy-2-methyl-5-oxocyclopenten-1-yl)-3-methylideneoxolan-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: 308.33

Molecular Weight (Monoisotopic): 308.1260

AlogP: 0.73

#Rotatable Bonds: 5

Polar Surface Area: 89.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: 2.02

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