10-Substituted artemisinin analogue

ID: ALA331309

Cas Number: 72826-63-2

PubChem CID: 12814879

Product Number: D137019, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H22O4

Molecular Weight: 266.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Deoxyartemisinin | Deoxyartemisinin|72826-63-2|Deoxy Artemisinin|2-deoxyartemisinin|(3R,3AS,3a1R,6R,6aS,9S,10aS)-3,6,9-trimethyldecahydro-2H-3a1,9-epoxyoxepino[4,3,2-ij]isochromen-2-one|J59T2407WZ|(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecan-10-one|Desoxyartemisinin|Hydroarteannuin|UNII-J59T2407WZ|Artemisinin, deoxy|(3R,3AS,3A1R,6R,6AS,9S,10AS)-3,6,9-TRIMETHYLDECAHYDRO-2H-3A1,9-EPOXYOXEPINO(4,3,2-IJ)ISOCHROMEN-2-ONE|Qing Hau Sau III|QINGHAOSU IShow More⌵

Canonical SMILES:  C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32O4

Standard InChI:  InChI=1S/C15H22O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

Standard InChI Key:  ZQGMLVQZBIKKMP-NNWCWBAJSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.1250   -3.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3817   -3.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981   -4.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -4.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8683   -3.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -6.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -6.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -6.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -6.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -6.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -5.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856   -4.0346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2959   -4.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3344   -5.1805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -6.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  5  4  1  0
 11  5  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  4  1  0
 14  8  1  0
 12 13  1  0
 13 14  1  0
 12  3  1  0
  8 15  1  6
 14 16  1  1
 13 17  2  0
  3 18  1  1
  4 19  1  6
 19  1  1  0
  1 20  1  6
  5 21  1  6
 11 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA331309

   DEOXYARTEMISININ

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: 266.34

Molecular Weight (Monoisotopic): 266.1518

AlogP: 2.46

#Rotatable Bonds: ┄

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 3.67

References

1. Avery MA, Alvim-Gaston M, Rodrigues CR, Barreiro EJ, Cohen FE, Sabnis YA, Woolfrey JR..  (2002)  Structure-activity relationships of the antimalarial agent artemisinin. 6. The development of predictive in vitro potency models using CoMFA and HQSAR methodologies.,  45  (2): [PMID:11784134] [10.1021/jm0100234]

2. Oh S, Jeong IH, Shin WS, Lee S..  (2003)  Growth inhibition activity of thioacetal artemisinin derivatives against human umbilical vein endothelial cells.,  13  (21): [PMID:14552753] [10.1016/j.bmcl.2003.08.023]

3. Avery MA, Muraleedharan KM, Desai PV, Bandyopadhyaya AK, Furtado MM, Tekwani BL..  (2003)  Structure-activity relationships of the antimalarial agent artemisinin. 8. design, synthesis, and CoMFA studies toward the development of artemisinin-based drugs against leishmaniasis and malaria.,  46  (20): [PMID:13678403] [10.1021/jm030181q]

4. Avery MA, Gao F, Chong WK, Mehrotra S, Milhous WK..  (1993)  Structure-activity relationships of the antimalarial agent artemisinin. 1. Synthesis and comparative molecular field analysis of C-9 analogs of artemisinin and 10-deoxoartemisinin.,  36  (26): [PMID:8277509] [10.1021/jm00078a017]

5. Brossi A, Venugopalan B, Dominguez Gerpe L, Yeh HJ, Flippen-Anderson JL, Buchs P, Luo XD, Milhous W, Peters W..  (1988)  Arteether, a new antimalarial drug: synthesis and antimalarial properties.,  31  (3): [PMID:3279208] [10.1021/jm00398a026]

6. Beekman AC, Barentsen AR, Woerdenbag HJ, Van Uden W, Pras N, Konings AW, el-Feraly FS, Galal AM, Wikström HV..  (1997)  Stereochemistry-dependent cytotoxicity of some artemisinin derivatives.,  60  (4): [PMID:9134741] [10.1021/np9605495]

7. Kaiser M, Wittlin S, Nehrbass-Stuedli A, Dong Y, Wang X, Hemphill A, Matile H, Brun R, Vennerstrom JL..  (2007)  Peroxide bond-dependent antiplasmodial specificity of artemisinin and OZ277 (RBx11160).,  51  (8): [PMID:17562801] [10.1128/aac.00225-07]

8. Nagamune K, Moreno SN, Sibley LD..  (2007)  Artemisinin-resistant mutants of Toxoplasma gondii have altered calcium homeostasis.,  51  (11): [PMID:17698618] [10.1128/aac.00582-07]

9. Fügi MA, Wittlin S, Dong Y, Vennerstrom JL..  (2010)  Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals.,  54  (3): [PMID:20028825] [10.1128/aac.01305-09]

Source

Source(1):

• Scientific Literature