Cylindroxanthone B

ID: ALA4587875

PubChem CID: 155567594

Max Phase: Preclinical

Molecular Formula: C21H20O8

Molecular Weight: 400.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(O)c(OC)c2oc3cc4c(c(O)c3c(=O)c2c1OC)C=CC(C)(C)O4

Standard InChI:  InChI=1S/C21H20O8/c1-21(2)7-6-9-10(29-21)8-11-12(14(9)22)15(23)13-17(25-3)19(26-4)16(24)20(27-5)18(13)28-11/h6-8,22,24H,1-5H3

Standard InChI Key:  CVILJWHJNNIMDV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.0455  -13.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4540  -14.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -12.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3927  -13.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1008  -14.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0990  -12.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8076  -12.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8064  -13.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5126  -14.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5149  -12.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2257  -12.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2240  -13.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9296  -14.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9289  -12.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5150  -11.6899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9270  -11.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6351  -12.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6336  -13.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3366  -14.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0470  -12.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3395  -12.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1024  -14.9680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3956  -15.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6847  -14.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6861  -12.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9784  -12.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0965  -11.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3876  -11.2898    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
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 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
  4 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4587875

   ---

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: 400.38

Molecular Weight (Monoisotopic): 400.1158

AlogP: 3.57

#Rotatable Bonds: 3

Polar Surface Area: 107.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.43

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.12

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: 2.43

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