(1aR,7aS,10aS,10bS,E)-5-(methoxymethyl)-1a-methyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-9(1aH)-one

ID: ALA4085298

PubChem CID: 137647064

Max Phase: Preclinical

Molecular Formula: C16H22O4

Molecular Weight: 278.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COC)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C16H22O4/c1-10-12-7-6-11(9-18-3)5-4-8-16(2)14(20-16)13(12)19-15(10)17/h5,12-14H,1,4,6-9H2,2-3H3/b11-5+/t12-,13-,14-,16+/m0/s1

Standard InChI Key:  ASKFVGDCSZDZIB-SOKXZRSZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.0683   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -3.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2764   -3.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -4.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5883   -4.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -4.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2391   -5.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5370   -6.1070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3665   -6.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5811   -5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490   -4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7883   -5.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483   -5.6986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -5.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6627   -2.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -2.6710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3439   -4.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811   -6.6982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355   -4.1685    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228   -6.1166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6696   -4.5936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8658   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
 12  8  1  0
  7  6  1  0
  6  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
 13 12  1  0
 14 13  1  0
 12 14  1  0
 13 15  1  1
  4 16  1  0
 16 17  1  0
 11 18  2  0
 10 19  2  0
 12 20  1  1
  8 21  1  1
  7 22  1  6
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085298

   ---

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: 278.35

Molecular Weight (Monoisotopic): 278.1518

AlogP: 2.39

#Rotatable Bonds: 2

Polar Surface Area: 48.06

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.34

Np Likeness Score: 3.17

References

1. Yang Z, Kuang B, Kang N, Ding Y, Ge W, Lian L, Gao Y, Wei Y, Chen Y, Zhang Q..  (2017)  Synthesis and anti-acute myeloid leukemia activity of C-14 modified parthenolide derivatives.,  127  [PMID:28068601] [10.1016/j.ejmech.2016.12.044]

Source

Source(1):

• Scientific Literature