15-formyl-12-isopropenyl-4-methyl-8-oxo-(6R,10S)-3,7,17-trioxatetracyclo[12.2.1.16,9.02,4]octadeca-1 (16),9 (18),14-trien-10-yl acetate (deoxylophotoxin)

ID: ALA50134

PubChem CID: 44296241

Max Phase: Preclinical

Molecular Formula: C22H24O7

Molecular Weight: 400.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: deoxylophotoxin | deoxylophotoxin|CHEMBL50134

Canonical SMILES:  C=C(C)[C@@H]1Cc2oc(cc2C=O)[C@@H]2O[C@@]2(C)C[C@@H]2C=C(C(=O)O2)[C@@H](OC(C)=O)C1

Standard InChI:  InChI=1S/C22H24O7/c1-11(2)13-5-17-14(10-23)7-19(28-17)20-22(4,29-20)9-15-8-16(21(25)27-15)18(6-13)26-12(3)24/h7-8,10,13,15,18,20H,1,5-6,9H2,2-4H3/t13-,15+,18+,20+,22+/m1/s1

Standard InChI Key:  NPZNRRDKNMSIDD-HGQVNPMOSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  1  0  0  0  0  0999 V2000
    4.9875   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -6.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -7.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -7.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -5.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -5.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -7.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -6.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -7.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -6.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6667   -7.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -6.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -8.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -8.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000   -8.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -4.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -8.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -7.9962    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677   -6.4770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4 13  2  0
  5  2  1  0
  6 12  1  0
  7  8  1  0
  8  5  1  0
  9 11  1  0
 10  4  1  0
 11  5  2  0
 15 12  1  0
 13 15  1  0
 14  1  1  0
 15 14  1  0
 16 17  1  0
 17  7  1  0
 18 10  1  0
 10 19  1  6
 16 20  1  1
 21 19  1  0
 22  6  2  0
 23  9  1  0
 24 21  2  0
 25 20  2  0
 26 23  2  0
  1 27  1  1
 28 20  1  0
 29 21  1  0
  2  3  1  0
  4  6  1  0
  7  9  2  0
 16 18  1  0
 15 30  1  1
  2 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA50134

   DEOXYLOPHOTOXIN

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: 400.43

Molecular Weight (Monoisotopic): 400.1522

AlogP: 3.23

#Rotatable Bonds: 3

Polar Surface Area: 95.34

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.84

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 3.19

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