4-isopropenyl-12-methyl-7-methyloxycarbonyl-17-oxo-(2S,4S,12R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-2-yl acetate (Lopholide)

ID: ALA54145

PubChem CID: 44296331

Max Phase: Preclinical

Molecular Formula: C23H26O9

Molecular Weight: 446.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1Cc2oc(cc2C(=O)OC)[C@@H]2O[C@@]2(C)C[C@H]2OC(=O)[C@@]3(O[C@H]23)[C@@H](OC(C)=O)C1

Standard InChI:  InChI=1S/C23H26O9/c1-10(2)12-6-14-13(20(25)27-5)8-15(29-14)18-22(4,31-18)9-16-19-23(32-19,21(26)30-16)17(7-12)28-11(3)24/h8,12,16-19H,1,6-7,9H2,2-5H3/t12-,16-,17+,18+,19-,22+,23-/m1/s1

Standard InChI Key:  QFVLPFJFNHETFU-PODBDYCPSA-N

Molfile:  

     RDKit          2D

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    5.6625   -5.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3625   -7.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2625   -8.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8875   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8875   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0417   -3.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3917   -8.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -8.0087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685   -6.4886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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  1  4  1  1
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 20 14  1  0
 14 21  1  6
 18 22  1  1
 23  8  2  0
 24 21  1  0
 25 17  2  0
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 27 22  2  0
  3 28  1  1
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 30 22  1  0
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 32 29  1  0
  2  4  1  0
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  5  6  1  0
  9 13  1  0
  9 11  2  0
 12 33  1  1
  5 34  1  6
  2 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA54145

   methyl (1R,2S,4S,10R,12S,14R,15R)-2-acetyloxy-12-methyl-17-oxo-4-prop-1-en-2-yl-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-diene-7-carboxylate

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: 446.45

Molecular Weight (Monoisotopic): 446.1577

AlogP: 2.42

#Rotatable Bonds: 3

Polar Surface Area: 117.10

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: 2.98

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