(1S,4S,5R,8S,9R,10R,12R,13R)-10-(2-bromoethyl)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

ID: ALA2368479

PubChem CID: 58623309

Max Phase: Preclinical

Molecular Formula: C17H27BrO4

Molecular Weight: 375.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H27BrO4/c1-10-4-5-13-11(2)14(7-9-18)19-15-17(13)12(10)6-8-16(3,20-15)21-22-17/h10-15H,4-9H2,1-3H3/t10-,11-,12+,13+,14-,15-,16+,17-/m1/s1

Standard InChI Key:  HKYZQQBQIMALCA-VBGZEHGNSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
   -3.8642    2.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578    2.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2364    1.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883    1.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4140    2.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045    1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9913    2.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    2.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247    1.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318    1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    0.2462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    0.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    3.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    2.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    1.4712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0319    1.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0167   -0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4574   -0.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1790   -1.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1886   -2.2307    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8988    0.4115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649    0.5390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    3.2899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  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
  1  3  1  0
 11 23  1  1
  9 24  1  6
  5 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2368479

   (1S,4S,5R,8S,9R,10R,12R,13R)-10-(2-bromoethyl)-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: 375.30

Molecular Weight (Monoisotopic): 374.1093

AlogP: 4.02

#Rotatable Bonds: 2

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: 3.25

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