Artonin O

ID: ALA1096733

Max Phase: Preclinical

Molecular Formula: C30H30O7

Molecular Weight: 502.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Artonin O

Canonical SMILES:  C=C(C)[C@H]1Cc2c(oc3cc(O)c(CC=C(C)C)c(O)c3c2=O)C2=C1C(=O)C(O)=C(CC=C(C)C)C2=O

Standard InChI:  InChI=1S/C30H30O7/c1-13(2)7-9-16-20(31)12-21-23(25(16)32)27(34)19-11-18(15(5)6)22-24(30(19)37-21)26(33)17(10-8-14(3)4)28(35)29(22)36/h7-8,12,18,31-32,35H,5,9-11H2,1-4,6H3/t18-/m1/s1

Standard InChI Key:  RREWBAHJGHVXMY-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    5.4027  -14.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4016  -15.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1164  -16.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146  -14.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8300  -14.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8288  -15.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418  -16.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5441  -14.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616  -14.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2581  -15.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9682  -16.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6863  -15.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9751  -14.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877  -14.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4039  -14.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4088  -13.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6915  -13.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782  -13.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882  -14.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6868  -16.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861  -16.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9713  -17.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707  -18.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2572  -16.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181  -16.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5409  -16.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1159  -14.8834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2648  -13.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1249  -13.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6930  -12.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4082  -11.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4098  -11.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1250  -10.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6960  -10.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3990  -16.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3954  -16.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152  -15.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0
 17 18  1  0
 18 13  1  0
  9  8  1  0
  1 19  1  0
  9 10  2  0
  2 20  1  0
  5  4  2  0
 20 21  1  0
  4  1  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
 22 24  1  0
  9 13  1  0
  3 25  1  0
 10 11  1  0
  7 26  2  0
 11 12  1  0
 15 27  2  0
 12 14  1  0
 18 28  2  0
  2  3  1  0
 16 29  1  0
  3  6  2  0
 17 30  1  0
 13 14  2  0
 30 31  1  0
  1  2  2  0
 31 32  2  0
 14 15  1  0
 32 33  1  0
  5  8  1  0
 32 34  1  0
 15 16  1  0
 12 35  1  1
  6  7  1  0
 35 36  1  0
 16 17  2  0
 35 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096733

   ARTONIN O

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: 502.56

Molecular Weight (Monoisotopic): 502.1992

AlogP: 5.54

#Rotatable Bonds: 5

Polar Surface Area: 125.04

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.16

CX Basic pKa: ┄

CX LogP: 6.03

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.36

Np Likeness Score: 2.21

References

1. Ren Y, Kardono LB, Riswan S, Chai H, Farnsworth NR, Soejarto DD, Carcache de Blanco EJ, Kinghorn AD..  (2010)  Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida.,  73  (5): [PMID:20384315] [10.1021/np1002065]

Source

Source(1):

• Scientific Literature