3-beta-oxy-iso-secotanapartholide

ID: ALA1085174

PubChem CID: 45111066

Max Phase: Preclinical

Molecular Formula: C15H18O5

Molecular Weight: 278.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h10-11,14,17H,2,4-6H2,1,3H3/t10-,11+,14+/m1/s1

Standard InChI Key:  XXYRTFCLQHKIDU-SUNKGSAMSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   11.9182    0.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7444    0.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9994    1.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3293    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6655    1.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8834    1.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7860    1.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4337    0.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2264    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9690   -0.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6354   -1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3037   -0.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0488    0.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0895   -0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6340   -1.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4507    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2749    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6722    1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4966    1.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2464    2.2890    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
  3  7  2  0
  1  8  1  0
  9  2  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 12 14  2  0
 11 15  2  0
 13 16  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085174

   (4R,5S)-5-[(3S)-3-hydroxy-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: 278.30

Molecular Weight (Monoisotopic): 278.1154

AlogP: 1.10

#Rotatable Bonds: 4

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.00

CX LogD: 1.00

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 2.59

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]

2. Boudermine S, Parisi V, Lemoui R, Boudiar T, Chini MG, Franceschelli S, Pecoraro M, Pascale M, Bifulco G, Braca A, De Tommasi N, De Leo M..  (2022)  Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts.,  85  (3.0): [PMID:35196017] [10.1021/acs.jnatprod.1c01211]

Source

Source(1):

• Scientific Literature