Artorigidin A

ID: ALA1094756

PubChem CID: 46834285

Max Phase: Preclinical

Molecular Formula: C30H32O7

Molecular Weight: 504.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@H]1Cc2c(oc3c(CC=C(C)C)c(O)c(CC=C(C)C)c(O)c3c2=O)-c2c(O)cc(O)c(O)c21

Standard InChI:  InChI=1S/C30H32O7/c1-13(2)7-9-16-25(33)17(10-8-14(3)4)29-24(26(16)34)27(35)19-11-18(15(5)6)22-23(30(19)37-29)20(31)12-21(32)28(22)36/h7-8,12,18,31-34,36H,5,9-11H2,1-4,6H3/t18-/m1/s1

Standard InChI Key:  LAAYVNVIRVOBNR-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.7554    0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -0.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0436    0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283    0.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275   -0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -0.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6179    0.6970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997   -0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167   -0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -0.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -1.7799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399   -1.7859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4700    0.6915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642    2.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4799    3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0510    3.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4714   -0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1854   -0.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6142   -0.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9008   -1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2514   -0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -1.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9655   -0.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    0.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    0.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2522    1.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    1.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105    1.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943    1.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9653    1.9562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  9  8  1  0
 17 18  2  0
  8  5  1  0
 18 19  1  0
  9 10  2  0
 18 20  1  0
  5  4  2  0
  2 21  1  0
  4  1  1  0
 21 22  1  0
 22 23  2  0
  2  3  1  0
 23 24  1  0
  9 29  1  0
 23 25  1  0
 10 11  1  0
 12 26  1  1
 11 12  1  0
 26 27  1  0
 12 30  1  0
 26 28  2  0
  5  6  1  0
  7 13  2  0
 29 30  2  0
  3  6  2  0
 30 31  1  0
  3 14  1  0
 31 32  2  0
  6  7  1  0
 32 33  1  0
  1 15  1  0
 33 34  2  0
 34 29  1  0
  7 10  1  0
 34 35  1  0
  4 16  1  0
 32 36  1  0
  1  2  2  0
 31 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094756

   ARTORIGIDIN A

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: 504.58

Molecular Weight (Monoisotopic): 504.2148

AlogP: 6.22

#Rotatable Bonds: 5

Polar Surface Area: 131.36

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 6.67

CX LogD: 5.35

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: 2.28

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]

2. Toume K, Habu T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M..  (2015)  Prenylated flavonoids and resveratrol derivatives isolated from Artocarpus communis with the ability to overcome TRAIL resistance.,  78  (1): [PMID:25537111] [10.1021/np500734t]

Source

Source(1):

• Scientific Literature