4,15-dimethyl-10-methylcarbonyloxy-12-(2-methyl-2-oxiranyl)-8-oxo-(6R,10S,13R)-3,7,17-trioxatetracyclo[12.2.1.16,9.02,4]octadeca-1 (16),9 (18),14-trien-13-yl acetate (Bipinnatin-H)

ID: ALA300903

PubChem CID: 44296260

Max Phase: Preclinical

Molecular Formula: C24H28O9

Molecular Weight: 460.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatin-H | Bipinnatin-H|CHEMBL300903

Canonical SMILES:  CC(=O)O[C@H]1C[C@H](C2(C)CO2)[C@@H](OC(C)=O)c2oc(cc2C)[C@@H]2O[C@@]2(C)C[C@@H]2C=C1C(=O)O2

Standard InChI:  InChI=1S/C24H28O9/c1-11-6-18-21-23(4,33-21)9-14-7-15(22(27)31-14)17(29-12(2)25)8-16(24(5)10-28-24)20(19(11)32-18)30-13(3)26/h6-7,14,16-17,20-21H,8-10H2,1-5H3/t14-,16-,17-,20+,21-,23-,24?/m0/s1

Standard InChI Key:  ZKPQWDXTJKFKDU-SZTWMKIDSA-N

Molfile:  

     RDKit          2D

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    4.4625   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6667   -8.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -8.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1292   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -8.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -7.8536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -6.3370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4 17  2  0
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  8 22  1  6
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  1 29  1  1
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  2  3  1  0
  4  9  1  0
  6 13  2  0
 10 18  1  0
 14 20  1  0
 21 34  1  1
  2 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA300903

   Bipinnatin-H

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: 460.48

Molecular Weight (Monoisotopic): 460.1733

AlogP: 3.00

#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: 12.84

CX Basic pKa: ┄

CX LogP: 1.59

CX LogD: 1.59

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: 2.76

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