Artemyrianolide E

ID: ALA4741149

PubChem CID: 162646766

Max Phase: Preclinical

Molecular Formula: C17H22O5

Molecular Weight: 306.36

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H22O5/c1-9-5-13(21-12(4)18)7-10(2)15(19)8-14-11(3)17(20)22-16(14)6-9/h5,13-16,19H,2-3,6-8H2,1,4H3/b9-5+/t13-,14+,15+,16-/m0/s1

Standard InChI Key:  FHHQOBBFSYZUAO-UDWIRWHESA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   11.4470  -12.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2303  -12.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6005  -12.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0416  -11.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3318  -12.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1760   -9.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8645   -9.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4876   -9.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3835  -10.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8154  -11.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3686  -11.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457  -10.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6622   -9.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2575  -10.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9639   -8.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3749  -10.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0222   -9.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3882  -12.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5812  -13.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7516  -12.5482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8283  -11.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4864   -8.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7782   -8.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1936   -8.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 11  5  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
  4 16  1  0
 14 17  1  6
  3 18  2  0
  2 19  2  0
  5 20  1  6
  4 21  1  1
  8 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741149

   ---

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: 306.36

Molecular Weight (Monoisotopic): 306.1467

AlogP: 2.06

#Rotatable Bonds: 1

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.46

Np Likeness Score: 3.38

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