tazopsine

ID: ALA493786

PubChem CID: 11653181

Max Phase: Preclinical

Molecular Formula: C18H23NO6

Molecular Weight: 349.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: tazopsine | tazopsine|CHEMBL493786|DTXSID201045607|Q15427893|(1S,8R,9R,12S,13S)-4,11-dimethoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10-tetraene-3,8,12,13-tetrol

Canonical SMILES:  COC1=C2[C@H]3NCC[C@]2(C[C@H](O)[C@@H]1O)c1c(ccc(OC)c1O)[C@H]3O

Standard InChI:  InChI=1S/C18H23NO6/c1-24-10-4-3-8-11(16(10)23)18-5-6-19-13(14(8)21)12(18)17(25-2)15(22)9(20)7-18/h3-4,9,13-15,19-23H,5-7H2,1-2H3/t9-,13+,14+,15-,18-/m0/s1

Standard InChI Key:  CQFMGBHPLGTYRE-ZERSTCQWSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -3.1348  -11.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359  -11.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075  -11.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4229  -10.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371  -13.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393  -14.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4268  -14.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104  -14.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4226  -13.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065  -13.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963  -13.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959  -12.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119  -11.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284  -12.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125  -12.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875  -13.6333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917  -12.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8554  -14.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301  -15.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8493  -10.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507  -12.4060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -9.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042  -14.0458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974  -14.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004  -15.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818  -11.9867    0.0000 O   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  2  0
  1  2  2  0
  9 15  1  6
  5  6  1  0
 11 16  1  0
  6  7  1  0
 16 17  1  0
 15 17  1  0
  7  8  1  0
  6 18  1  1
  8 10  2  0
  7 19  1  1
  9 10  1  0
  1 20  1  0
  3  4  2  0
  2 21  1  0
  4  1  1  0
 20 22  1  0
  9  5  1  0
 11 23  1  1
  2 14  1  0
  8 24  1  0
 24 25  1  0
 13  3  1  0
 12 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA493786

   TAZOPSINE

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: 349.38

Molecular Weight (Monoisotopic): 349.1525

AlogP: 0.07

#Rotatable Bonds: 2

Polar Surface Area: 111.41

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.57

CX Basic pKa: 8.19

CX LogP: -1.48

CX LogD: -2.18

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: 1.91

References

1. Carraz M, Jossang A, Rasoanaivo P, Mazier D, Frappier F..  (2008)  Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.,  16  (11): [PMID:18456502] [10.1016/j.bmc.2008.04.033]

2. Rodrigues T, Prudêncio M, Moreira R, Mota MM, Lopes F..  (2012)  Targeting the liver stage of malaria parasites: a yet unmet goal.,  55  (3): [PMID:22122518] [10.1021/jm201095h]

Source

Source(1):

• Scientific Literature