Crassalactone C

ID: ALA4127227

PubChem CID: 145962781

Max Phase: Preclinical

Molecular Formula: C22H20O6

Molecular Weight: 380.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)O[C@H](c1ccccc1)[C@@H]1O[C@@H]2CC(=O)O[C@@H]2[C@H]1O

Standard InChI:  InChI=1S/C22H20O6/c23-17(12-11-14-7-3-1-4-8-14)27-20(15-9-5-2-6-10-15)22-19(25)21-16(26-22)13-18(24)28-21/h1-12,16,19-22,25H,13H2/b12-11+/t16-,19-,20-,21+,22-/m1/s1

Standard InChI Key:  GDYNBHXFRSGEGM-CLMFUUGZSA-N

Molfile:  

     RDKit          2D

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   19.0158   -6.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3432   -5.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.6804   -6.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8553   -6.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5945   -7.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2611   -7.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2470   -7.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8040   -6.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.2449   -7.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8556   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.8196   -6.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2034   -6.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9230   -7.9607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0091   -5.5221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7600   -5.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9316   -4.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3723   -5.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7154   -3.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8870   -3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6705   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8422   -2.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4428   -1.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2748   -2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  0
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  1  9  1  6
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 10 12  1  6
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  7 18  2  0
  5 19  1  6
  4 20  1  6
  2 21  1  6
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 25 26  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4127227

   ---

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: 380.40

Molecular Weight (Monoisotopic): 380.1260

AlogP: 2.43

#Rotatable Bonds: 5

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.01

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 1.57

References

1. Markovič M, Koóš P, Čarný T, Sokoliová S, Boháčiková N, Moncol J, Gracza T..  (2017)  Total Synthesis, Configuration Assignment, and Cytotoxic Activity Evaluation of Protulactone A.,  80  (5): [PMID:28418248] [10.1021/acs.jnatprod.7b00212]

Source

Source(1):

• Scientific Literature