Artemyrianolide Q

ID: ALA4743993

PubChem CID: 13817984

Max Phase: Preclinical

Molecular Formula: C15H20O3

Molecular Weight: 248.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11+,12+,13+,15+/m0/s1

Standard InChI Key:  GTYUWNQOOLJZBM-KMCWBVRRSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   39.1963  -11.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2004  -10.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4906  -10.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9433   -9.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6777   -9.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5189  -10.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0149  -10.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2024   -9.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5048   -9.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8860   -9.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8558  -10.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3371  -11.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7761  -11.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5663  -11.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6154  -10.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9526   -8.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1973  -12.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1951   -8.7373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.4772  -12.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1196  -11.7874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   42.4320   -9.7857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   39.7989  -11.1353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  8  4  1  0
  4  5  1  0
  5 11  1  0
  7  6  1  0
  6 12  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  2  7  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  4 16  2  0
 14 17  2  0
  8 18  1  6
 13 19  2  0
 12 20  1  6
 11 21  1  6
  7 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4743993

   (3aR,5aR,8R,8aR,9aR)-8-hydroxy-8-methyl-1,5-dimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

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: 248.32

Molecular Weight (Monoisotopic): 248.1412

AlogP: 2.21

#Rotatable Bonds: ┄

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.03

CX LogD: 2.03

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.41

Np Likeness Score: 3.64

References

1. Tang S,Zhang XT,Ma YB,Huang XY,Geng CA,Li TZ,Zhang XM,Shen C,Su LH,Gao Z,Chen JJ.  (2020)  Artemyrianolides A-S, Cytotoxic Sesquiterpenoids from Artemisia myriantha.,  83  (9.0): [PMID:32842729] [10.1021/acs.jnatprod.0c00396]

Source

Source(1):

• Scientific Literature