Pyrethrosin

ID: ALA517337

Cas Number: 28272-18-6

PubChem CID: 5281496

Max Phase: Preclinical

Molecular Formula: C17H22O5

Molecular Weight: 306.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pyrethrosin | Pyrethrosin|CHEBI:8661|Z13OX0769A|28272-18-6|CHEMBL517337|UNII-Z13OX0769A|NSC-22070|NSC 22070|C09536|AI3-31868|PYRETHROSIN [MI]|SCHEMBL5188143|DTXSID701018639|Q27108132|[(1S,3R,5R,8E,10R,11R)-3,8-dimethyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-en-10-yl] acetate|Germacra-4,11(13)-dien-12-oic acid, 1-beta,10-epoxy-6-alpha,8-alpha-dihydroxy-, 12,8-lactone, acetate, (E)-|Germacra-4,11(13)-dien-12-oic acid, 1.beta.,10-epoxy-6.alpha.,8.alpha.-dihydroxy-, 12,8-lactShow More⌵

Canonical SMILES:  C=C1C(=O)O[C@H]2C[C@@]3(C)O[C@@H]3CC/C(C)=C/[C@@H](OC(C)=O)[C@H]12

Standard InChI:  InChI=1S/C17H22O5/c1-9-5-6-14-17(4,22-14)8-13-15(10(2)16(19)21-13)12(7-9)20-11(3)18/h7,12-15H,2,5-6,8H2,1,3-4H3/b9-7+/t12-,13+,14-,15+,17-/m1/s1

Standard InChI Key:  JJMLQAVFDJXJAL-AWZCNKNJSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -4.5850    1.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    1.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727    0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    1.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549    0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479    2.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343    1.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358    1.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517    0.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3597    1.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4599   -0.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -0.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -1.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -0.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423    0.3418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423    2.8177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551    1.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1634    1.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586    2.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933    3.1303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8718   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 12  2  0
  4  5  1  0
  9 13  2  0
  5  8  1  0
  5 14  1  6
  7  6  1  0
 14 15  1  0
  7  8  1  0
  2  3  1  0
 15 16  2  0
 15 17  1  0
  3  4  2  0
  8 18  1  6
  1  2  1  0
  7 19  1  1
 22 20  1  1
 22 21  1  0
 23 22  1  0
 21 23  1  0
  1 21  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 21 24  1  6
 11  7  1  0
  3 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517337

   PYRETHROSIN

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: 306.36

Molecular Weight (Monoisotopic): 306.1467

AlogP: 2.30

#Rotatable Bonds: 1

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: 1.94

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.32

Np Likeness Score: 3.66

References

1. Galal AM..  (2001)  Microbial transformation of pyrethrosin.,  64  (8): [PMID:11520238] [10.1021/np0100082]

Source

Source(1):

• Scientific Literature