Eupahyssopin

ID: ALA3276960

Cas Number: 57718-77-1

PubChem CID: 5281454

Max Phase: Preclinical

Molecular Formula: C20H26O7

Molecular Weight: 378.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)/C(C)=C/CO)C/C(C)=C/CC[C@@]1(CO)O[C@H]21

Standard InChI:  InChI=1S/C20H26O7/c1-11-5-4-7-20(10-22)17(27-20)16-15(13(3)19(24)26-16)14(9-11)25-18(23)12(2)6-8-21/h5-6,14-17,21-22H,3-4,7-10H2,1-2H3/b11-5+,12-6+/t14-,15-,16+,17-,20+/m1/s1

Standard InChI Key:  CWNJPEXNWXFLHM-RAMABSIPSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    5.2766   -9.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0180  -10.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1963  -11.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285  -10.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -9.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995  -10.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6741  -11.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502  -11.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939  -12.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2593  -12.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9269  -12.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3391  -11.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191  -11.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9911  -11.7992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2575  -13.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7109  -12.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4962  -11.7091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9989  -11.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5797  -10.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776  -10.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3627   -9.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5946  -11.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9584  -10.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7562  -10.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3372   -9.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2860   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336  -10.8340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6918  -11.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858  -10.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357  -12.1209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0
  1  2  1  0
  2  3  1  0
 12  8  1  0
  3  7  1  0
  4  5  1  0
  5  6  1  0
  6 13  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 13 12  1  0
 14 13  1  0
 12 14  1  0
 10 15  2  0
 11 16  2  0
  7 17  1  6
  3 18  1  1
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 20 23  2  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
 12 27  1  6
 13 28  1  1
 28 29  1  0
  8 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3276960

   CID 5281454

Molecule Features

Natural Product: No

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: 378.42

Molecular Weight (Monoisotopic): 378.1679

AlogP: 1.19

#Rotatable Bonds: 4

Polar Surface Area: 105.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.61

CX LogD: 1.61

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 3.55

References

1. Lee KH, Wu YS, Hall IH..  (1977)  Antitumor agents. 25. Synthesis and antitumor activity of uracil and thymine alpha-methylene-gamma-lactones and related derivatives.,  20  (7): [PMID:874966] [10.1021/jm00217a009]

Source

Source(1):

• Scientific Literature