Chrysanolide I

ID: ALA4527273

PubChem CID: 155544260

Max Phase: Preclinical

Molecular Formula: C20H28O6

Molecular Weight: 364.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C(\C)C(=O)O[C@H]1CC(C)=C2C[C@H](O)[C@](C)(O)[C@@H]2[C@H]2OC(=O)[C@@H](C)[C@@H]21

Standard InChI:  InChI=1S/C20H28O6/c1-6-9(2)18(22)25-13-7-10(3)12-8-14(21)20(5,24)16(12)17-15(13)11(4)19(23)26-17/h6,11,13-17,21,24H,7-8H2,1-5H3/b9-6+/t11-,13-,14-,15+,16-,17-,20-/m0/s1

Standard InChI Key:  JUDSHVJBQAIZGM-UMDJFNJOSA-N

Molfile:  

 
     RDKit          2D

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   19.0678  -21.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0761  -20.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3415  -20.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7930  -19.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5162  -19.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6970  -20.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1838  -20.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3802  -20.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1262  -21.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7771  -22.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4300  -21.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9857  -20.9952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7753  -23.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723  -20.2936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.1943  -22.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5388  -20.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9584  -19.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8004  -19.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5361  -18.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2227  -20.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2200  -18.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0661  -18.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8752  -20.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0625  -19.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3756  -19.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7641  -19.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9441  -19.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8012  -18.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8685  -21.1933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
 24  4  2  0
  4  5  1  0
  5  6  1  0
 23  8  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  7 12  1  6
 10 13  2  0
  8 14  1  1
 11 15  1  6
  6 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 18 21  2  0
 21 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26  2  1  0
  2 23  1  0
 26 27  1  1
  4 28  1  0
 23 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4527273

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.44

Molecular Weight (Monoisotopic): 364.1886

AlogP: 1.89

#Rotatable Bonds: 2

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: ┄

CX LogP: 1.62

CX LogD: 1.62

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 3.26

References

1. Luo P, Cheng Y, Yin Z, Li C, Xu J, Gu Q..  (2019)  Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from the Aerial Parts of Chrysanthemum indicum.,  82  (2): [PMID:30726671] [10.1021/acs.jnatprod.8b00863]

Source

Source(1):

• Scientific Literature