(4R,5S)-5-(3,5-dihydroxy-2-methylcyclopent-1-enyl)-3-methylene-4-(3-oxobutyl)dihydrofuran-2(3H)-one

ID: ALA1085175

PubChem CID: 46881371

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(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-JENJKZFGSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.6702   -5.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439   -5.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -4.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2592   -4.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -4.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7048   -4.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8025   -4.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545   -6.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -6.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6195   -6.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532   -7.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2849   -6.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -6.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4994   -7.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546   -8.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1379   -5.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139   -5.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -4.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9074   -4.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -3.8521    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  0
  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:

   

   ALA1085175

   (4R,5S)-5-(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]

Source

Source(1):

• Scientific Literature