(+)-Arteglasin A

ID: ALA4518431

Cas Number: 33204-39-6

PubChem CID: 169494

Max Phase: Preclinical

Molecular Formula: C17H20O5

Molecular Weight: 304.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(C)=O)CC(C)=C1C[C@H]3O[C@@]3(C)[C@@H]12

Standard InChI:  InChI=1S/C17H20O5/c1-7-5-11(20-9(3)18)13-8(2)16(19)21-15(13)14-10(7)6-12-17(14,4)22-12/h11-15H,2,5-6H2,1,3-4H3/t11-,12+,13+,14-,15-,17+/m0/s1

Standard InChI Key:  IJNUSISHBLGZMG-JMZZHWKLSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   27.6260  -11.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3677  -11.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1020  -11.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9892  -10.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9391  -12.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4297  -12.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6630  -12.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7492  -10.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2842  -12.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7614  -12.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2046  -13.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9989  -13.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0480  -12.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7369  -12.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6299  -13.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8605  -11.6553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.7449  -10.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4547   -9.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0310   -9.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4846  -13.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6998  -13.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9023  -14.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6937  -14.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1130  -13.9129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.3417  -12.1588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.3458  -13.5827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  6  2  0
  3  9  1  0
  5 10  1  0
  1  4  1  0
  5  6  1  0
  6  7  1  0
  7 21  1  0
 20  5  1  0
  3  8  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 13 14  2  0
 12 15  2  0
  9 16  1  6
  8 17  1  0
 17 18  1  0
 17 19  2  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
 20 23  1  1
 21 24  1  1
  5 25  1  6
 10 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4518431

   Arteglasin A

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: 304.34

Molecular Weight (Monoisotopic): 304.1311

AlogP: 1.91

#Rotatable Bonds: 1

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.15

CX LogD: 1.15

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.32

Np Likeness Score: 3.60

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