Rhytidone A

ID: ALA4096269

PubChem CID: 137655721

Max Phase: Preclinical

Molecular Formula: C20H22O6

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@H]1[C@@H]2[C@H]([C@@H](O)CCC23Oc2cccc4cccc(c24)O3)[C@@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C20H22O6/c21-11-7-8-20(18-17(11)12(22)9-13(23)19(18)24)25-14-5-1-3-10-4-2-6-15(26-20)16(10)14/h1-6,11-13,17-19,21-24H,7-9H2/t11-,12-,13-,17+,18-,19+/m0/s1

Standard InChI Key:  JNPNKBNCYQQGCP-HTUUWXQOSA-N

Molfile:  

     RDKit          2D

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   25.8516  -19.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8443  -18.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1287  -18.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1332  -19.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5606  -22.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2822  -22.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2779  -21.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8456  -22.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4171  -21.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4196  -22.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1323  -22.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1331  -21.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8432  -21.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5558  -21.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5635  -20.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1355  -20.3535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5604  -18.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5673  -19.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2780  -19.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2682  -18.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2637  -17.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9858  -18.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9894  -19.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2842  -20.7574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8420  -17.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8471  -19.1134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.2721  -19.1134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.7059  -19.9258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0
  1  4  1  0
 17  2  1  0
  2  3  1  0
  3  4  1  0
  8  5  1  0
  5  6  2  0
  6  7  1  0
  7 14  2  0
  8 13  1  0
 12  9  1  0
  9 10  2  0
 10 11  1  0
 11  8  2  0
 12 13  2  0
 12 16  1  0
 13 14  1  0
 14 15  1  0
  1 15  1  0
  1 16  1  0
 17 18  1  0
 17 20  1  0
 18 19  1  0
 19 23  1  0
 22 20  1  0
 20 21  1  1
 23 22  1  0
 19 24  1  1
  2 25  1  6
 18 26  1  6
 17 27  1  1
 23 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4096269

   ---

Molecule Features

Natural Product: Yes

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: 358.39

Molecular Weight (Monoisotopic): 358.1416

AlogP: 1.18

#Rotatable Bonds: ┄

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.55

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: 1.76

References

1. Siridechakorn I, Yue Z, Mittraphab Y, Lei X, Pudhom K..  (2017)  Identification of spirobisnaphthalene derivatives with anti-tumor activities from the endophytic fungus Rhytidhysteron rufulum AS21B.,  25  (11): [PMID:28274675] [10.1016/j.bmc.2017.02.054]

Source

Source(1):

• Scientific Literature