(-)-Lychnopholide

ID: ALA4476580

Cas Number: 77448-64-7

PubChem CID: 49767028

Max Phase: Preclinical

Molecular Formula: C20H22O6

Molecular Weight: 358.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2/C=C(/C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)/C(C)=C\C)[C@@H]12)O3

Standard InChI:  InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17+,20-/m1/s1

Standard InChI Key:  QATUWZPYBIHFFR-UVXIKMMUSA-N

Molfile:  

 
     RDKit          2D

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   11.8369  -15.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4999  -14.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2455  -13.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4283  -13.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1739  -14.5699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8245  -12.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8245  -13.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8493  -13.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8493  -12.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8823  -12.0804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5453  -11.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2909  -10.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4737  -10.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2193  -11.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1365  -11.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2484  -11.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7710  -10.1603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5291  -13.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2370  -13.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9445  -13.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2376  -12.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9439  -14.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6525  -13.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2767  -14.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369  -15.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6111  -13.7891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -13.7891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6530  -12.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  1  0
  1  2  1  0
  3  4  1  0
  5  1  1  0
  6  7  1  0
  7  3  1  0
  4  8  1  0
  8  9  2  0
 13 14  2  0
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 12 13  1  0
 14 10  1  0
  9 14  1  0
  6 11  1  0
  9 15  1  0
 11 16  1  6
 12 17  2  0
  7 18  1  6
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 20 23  2  0
  2 24  2  0
  1 25  2  0
  4 26  1  1
  3 27  1  6
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476580

   Lychnopholide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.39

Molecular Weight (Monoisotopic): 358.1416

AlogP: 2.55

#Rotatable Bonds: 2

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: 3.37

References

1. Ren Y, de Blanco EJC, Fuchs JR, Soejarto DD, Burdette JE, Swanson SM, Kinghorn AD..  (2019)  Potential Anticancer Agents Characterized from Selected Tropical Plants.,  82  (3): [PMID:30830783] [10.1021/acs.jnatprod.9b00018]

Source

Source(1):

• Scientific Literature