5-hydroxy-4-(1-hydroxymethylvinyl)-7,12-dimethyl-17-oxo-(2S,4R,5R,12R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-2-yl acetate

ID: ALA430757

PubChem CID: 44296236

Max Phase: Preclinical

Molecular Formula: C22H26O9

Molecular Weight: 434.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CO)[C@H]1C[C@H](OC(C)=O)[C@@]23O[C@@H]2[C@@H](C[C@]2(C)O[C@H]2c2cc(C)c(o2)[C@@H]1O)OC3=O

Standard InChI:  InChI=1S/C22H26O9/c1-9-5-13-18-21(4,30-18)7-14-19-22(31-19,20(26)29-14)15(27-11(3)24)6-12(10(2)8-23)16(25)17(9)28-13/h5,12,14-16,18-19,23,25H,2,6-8H2,1,3-4H3/t12-,14-,15+,16-,18+,19-,21+,22-/m1/s1

Standard InChI Key:  VYEIAQHPZWBDHX-NAXQBTESSA-N

Molfile:  

     RDKit          2D

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    5.6500   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2042   -6.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3500   -7.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5667   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -7.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -8.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -6.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -8.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428   -7.6110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -6.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1170   -7.4635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 17  1  0
  1  4  1  1
  5  3  1  0
  3  6  1  0
  7  1  1  0
  8  5  1  0
  9 16  1  0
 10  9  1  0
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 12 20  1  6
 18 21  1  1
 22  7  2  0
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  3 26  1  1
 16 27  1  6
 28 14  1  0
 29 21  1  0
 30 29  1  0
 31 23  1  0
  2  4  1  0
 11 13  1  0
  5  6  1  0
  8 10  1  0
  8 15  2  0
 11 32  1  1
  5 33  1  6
  2 34  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA430757

   [(1R,2S,4R,5R,10R,12S,14R,15R)-5-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-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: 434.44

Molecular Weight (Monoisotopic): 434.1577

AlogP: 1.40

#Rotatable Bonds: 3

Polar Surface Area: 131.26

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: ┄

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 3.32

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