papilistatin

ID: ALA1087295

PubChem CID: 46184319

Max Phase: Preclinical

Molecular Formula: C18H12O7

Molecular Weight: 340.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Papilistatin | 8-Methoxyphenanthro[3,4-D][1,3]dioxole-5,6-Dicarboxylic Acid|papilistatin|CHEMBL1087295|Q27451756

Canonical SMILES:  COc1cccc2c1cc(C(=O)O)c1c(C(=O)O)cc3c(c12)OCO3

Standard InChI:  InChI=1S/C18H12O7/c1-23-12-4-2-3-8-9(12)5-10(17(19)20)14-11(18(21)22)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)(H,21,22)

Standard InChI Key:  KTEBZKXXNMHJFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.7853    1.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001    1.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995    0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    0.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -1.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -1.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2165   -1.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -2.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846   -1.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126    0.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2113    1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9986    1.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4866    0.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0006    0.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    1.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    1.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    2.5544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415    0.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736   -0.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -2.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704   -3.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 11 12  2  0
 12  7  1  0
 13 14  2  0
  3  6  1  0
  4  8  1  0
  7  5  1  0
  5  6  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  3  4  2  0
  1 18  1  0
  7  8  2  0
 18 19  2  0
 18 20  1  0
  8  9  1  0
  6 21  1  0
  3  1  1  0
 21 22  1  0
  9 10  2  0
 21 23  2  0
 13  4  1  0
 12 24  1  0
 10 11  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1087295

   PAPILISTATIN

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: 340.29

Molecular Weight (Monoisotopic): 340.0583

AlogP: 3.13

#Rotatable Bonds: 3

Polar Surface Area: 102.29

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: -3.99

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: 0.74

References

1. Pettit GR, Ye Q, Herald DL, Hogan F, Pettit RK..  (2010)  Antineoplastic agents. 573. isolation and structure of papilistatin from the papilionid butterfly Byasa polyeuctes termessa.,  73  (2): [PMID:20085286] [10.1021/np9004689]

Source

Source(1):

• Scientific Literature