Pretazettine

ID: ALA518912

Cas Number: 17322-85-9

PubChem CID: 73360

Max Phase: Preclinical

Molecular Formula: C18H21NO5

Molecular Weight: 331.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1C=C[C@@]23c4cc5c(cc4[C@H](O)O[C@H]2CN(C)[C@H]3C1)OCO5

Standard InChI:  InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17-,18+/m1/s1

Standard InChI Key:  KLJOYDMUWKSYBP-YNBLHMCPSA-N

Molfile:  

     RDKit          2D

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   -1.4708   -7.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7629   -6.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908   -6.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -7.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -9.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1754   -9.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624   -9.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -9.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426   -8.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026   -9.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -8.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -8.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8799   -8.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899   -9.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1751   -8.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4647  -10.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -7.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -8.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625   -8.9542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515   -6.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818   -5.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7690   -5.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -6.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
 12  7  1  0
  7  8  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 17 18  2  0
 17 13  1  0
 18  8  1  0
 18  1  1  0
  1  2  1  0
  9 19  1  1
  1  6  1  6
  2 20  1  0
  2  3  1  0
 20 21  1  0
 11 21  1  0
  3  4  1  0
 11 22  1  1
  8  9  1  0
 20 23  1  0
  9 10  1  0
  4 24  1  1
 10 11  1  0
 24 25  1  0
 11  1  1  0
  2 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA518912

   Pretazettine

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: 331.37

Molecular Weight (Monoisotopic): 331.1420

AlogP: 1.33

#Rotatable Bonds: 1

Polar Surface Area: 60.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.54

CX Basic pKa: 7.71

CX LogP: 1.10

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 2.50

References

1. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature