Cylindroxanthone A

ID: ALA4461541

PubChem CID: 155528646

Max Phase: Preclinical

Molecular Formula: C22H22O8

Molecular Weight: 414.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(OC)c(OC)c2c(=O)c3c(O)c4c(cc3oc2c1OC)OC(C)(C)C=C4

Standard InChI:  InChI=1S/C22H22O8/c1-22(2)8-7-10-11(30-22)9-12-13(15(10)23)16(24)14-17(25-3)19(26-4)21(28-6)20(27-5)18(14)29-12/h7-9,23H,1-6H3

Standard InChI Key:  HTKCMAWVRUHFSK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.2630  -19.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4458  -19.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8544  -19.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7942  -18.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7931  -19.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5011  -19.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4993  -17.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2079  -18.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2068  -19.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9130  -19.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9153  -17.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6260  -18.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6243  -19.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3299  -19.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3292  -17.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9153  -17.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3273  -17.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0354  -18.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0340  -19.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7370  -19.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4474  -18.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7399  -17.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5028  -20.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7959  -20.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0850  -19.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3776  -19.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0864  -17.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0862  -17.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4969  -17.1731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2034  -16.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 19  2  0
 18 15  2  0
 15 12  1  0
 11 16  2  0
 15 17  1  0
 18 19  1  0
 18 22  1  0
 19 20  1  0
 20  2  1  0
  2 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  1  0
  5 25  1  0
 25 26  1  0
  4 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461541

   ---

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: 414.41

Molecular Weight (Monoisotopic): 414.1315

AlogP: 3.87

#Rotatable Bonds: 4

Polar Surface Area: 96.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.19

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.51

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: 2.25

References

1. Sukandar ER, Kaennakam S, Rassamee K, Ersam T, Siripong P, Tip-Pyang S..  (2019)  Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.,  82  (5): [PMID:30978023] [10.1021/acs.jnatprod.9b00046]

Source

Source(1):

• Scientific Literature