8-ethoxy-7-formyl-3-hydroxy-10-isopropenyl-3-methyl-17-oxo-(1R,10S,12S)-14,16,18-trioxatetracyclo[11.2.2.15,8.013,15]octadeca-4,6-dien-12-yl acetate

ID: ALA296630

PubChem CID: 44296113

Max Phase: Preclinical

Molecular Formula: C24H30O9

Molecular Weight: 462.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@H]1C[C@H](OC(C)=O)[C@@]23O[C@@H]2[C@@H](C[C@](C)(O)/C=C2/C=C(C=O)C(OCC)(C1)O2)OC3=O

Standard InChI:  InChI=1S/C24H30O9/c1-6-29-23-9-15(13(2)3)7-19(30-14(4)26)24-20(33-24)18(31-21(24)27)11-22(5,28)10-17(32-23)8-16(23)12-25/h8,10,12,15,18-20,28H,2,6-7,9,11H2,1,3-5H3/b17-10-/t15-,18+,19-,20+,22+,23?,24+/m0/s1

Standard InChI Key:  JAYRBXGJZSQPST-QXQIGULQSA-N

Molfile:  

     RDKit          2D

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    1.4542   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -4.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7167   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794   -5.4346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  3  1  1
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 16 28  1  1
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  2  3  1  0
  7  9  1  0
 10 11  1  0
 10 12  1  0
  7 34  1  1
  2 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA296630

   [(1R,2S,4S,9Z,11S,13R,14R)-6-ethoxy-7-formyl-11-hydroxy-11-methyl-16-oxo-4-prop-1-en-2-yl-15,17,18-trioxatetracyclo[11.2.2.16,9.01,14]octadeca-7,9-dien-2-yl] acetate

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: 462.50

Molecular Weight (Monoisotopic): 462.1890

AlogP: 1.88

#Rotatable Bonds: 5

Polar Surface Area: 120.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.10

CX LogD: 1.10

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: 2.65

References

1. Abramson SN, Trischman JA, Tapiolas DM, Harold EE, Fenical W, Taylor P..  (1991)  Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists.,  34  (6): [PMID:1676426] [10.1021/jm00110a007]

Source

Source(1):

• Scientific Literature