Eudesmaafraglaucolide

ID: ALA4514117

PubChem CID: 14021352

Max Phase: Preclinical

Molecular Formula: C19H24O7

Molecular Weight: 364.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1[C@@H](OC(C)=O)C[C@@H](O)[C@]2(C)CCC3=C(COC(C)=O)C(=O)O[C@@H]3[C@@H]12

Standard InChI:  InChI=1S/C19H24O7/c1-9-14(25-11(3)21)7-15(22)19(4)6-5-12-13(8-24-10(2)20)18(23)26-17(12)16(9)19/h14-17,22H,1,5-8H2,2-4H3/t14-,15+,16+,17-,19-/m0/s1

Standard InChI Key:  RLPORGYBFRWYDX-ATIFRJIPSA-N

Molfile:  

 
     RDKit          2D

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   37.2384   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2384   -4.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9514   -4.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9514   -3.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6645   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6610   -4.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3709   -4.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0888   -4.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3779   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0897   -3.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7003   -2.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3701   -2.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5513   -2.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7836   -1.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9514   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5217   -3.1302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5193   -2.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8025   -1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2335   -1.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9524   -5.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6531   -5.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3708   -3.9536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.5073   -3.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0635   -2.5609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8705   -2.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4266   -2.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1213   -3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6645   -2.7180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  3  2  1  0
  6  3  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  9 13  1  0
 12 14  2  0
  4 15  2  0
  1 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
  3 20  1  6
  6 21  1  6
  9 22  1  6
 11 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  5 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4514117

   [(5aR,6R,8S,9aS,9bR)-8-acetyloxy-6-hydroxy-5a-methyl-9-methylidene-2-oxo-5,6,7,8,9a,9b-hexahydro-4H-benzo[g][1]benzofuran-3-yl]methyl acetate

Molecule Features

Natural Product: Yes

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: 364.39

Molecular Weight (Monoisotopic): 364.1522

AlogP: 1.44

#Rotatable Bonds: 3

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: 3.23

References

1. Reinhardt JK, Klemd AM, Danton O, De Mieri M, Smieško M, Huber R, Bürgi T, Gründemann C, Hamburger M..  (2019)  Sesquiterpene Lactones from Artemisia argyi: Absolute Configuration and Immunosuppressant Activity.,  82  (6): [PMID:31181920] [10.1021/acs.jnatprod.8b00791]

2. Dürr L, Reinhardt JK, Dobrzyński M, Hell T, Smieško M, Pertz O, Hamburger M, Garo E..  (2022)  A Dimerosesquiterpene and Sesquiterpene Lactones from Artemisia argyi Inhibiting Oncogenic PI3K/AKT Signaling in Melanoma Cells.,  85  (11.0): [PMID:36351173] [10.1021/acs.jnatprod.2c00471]

Source

Source(1):

• Scientific Literature