(1S,4S,5R,8S,9R,10R,12S,13R)-10-(ethylsulfanyl)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

ID: ALA2368476

PubChem CID: 73346846

Max Phase: Preclinical

Molecular Formula: C17H28O4S

Molecular Weight: 328.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS[C@H]1O[C@@H]2O[C@]3(C)CC[C@H]4[C@H](C)CC[C@@H]([C@H]1C)[C@@]24OO3

Standard InChI:  InChI=1S/C17H28O4S/c1-5-22-14-11(3)13-7-6-10(2)12-8-9-16(4)19-15(18-14)17(12,13)21-20-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,16+,17-/m1/s1

Standard InChI Key:  LSTVIQWGCBMICO-VBGZEHGNSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
   -3.6839  -17.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8776  -17.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0561  -18.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081  -18.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339  -17.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246  -18.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114  -17.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5183  -17.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448  -18.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518  -18.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637  -18.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748  -19.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677  -20.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496  -19.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062  -16.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432  -17.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799  -18.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8516  -18.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369  -20.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774  -20.9168    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9988  -21.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085  -22.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7188  -19.5058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850  -19.3783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458  -16.6276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1  2  1  0
  8 15  1  6
  5  8  1  0
  9  6  1  0
  6  7  1  0
  3 16  1  0
  7  8  1  0
 10 17  1  6
 16 17  1  0
  9 10  1  0
  3 18  1  1
  3  4  1  0
  4 11  1  0
 14 19  1  1
  5 10  1  0
 13 20  1  1
  5  2  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  1
  9 24  1  6
  5 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2368476

   (1S,4S,5R,8S,9R,10R,12S,13R)-10-ethylsulfanyl-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane

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: 328.47

Molecular Weight (Monoisotopic): 328.1708

AlogP: 3.95

#Rotatable Bonds: 2

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: 2.85

References

1. Jung M, Tak J, Chung WY, Park KK..  (2006)  Antiangiogenic activity of deoxoartemisinin derivatives on chorioallantoic membrane.,  16  (5): [PMID:16380253] [10.1016/j.bmcl.2005.11.074]

Source

Source(1):

• Scientific Literature