Microhelenalin B

ID: ALA4878114

Cas Number: 63569-08-4

PubChem CID: 182376

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(C)C(=O)O[C@H]1[C@@H]2[C@H](C)C(=O)O[C@@H]2C[C@@H](C)[C@@H]2C=CC(=O)[C@]21C

Standard InChI:  InChI=1S/C20H28O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h7-8,10-14,16-17H,6,9H2,1-5H3/t10?,11-,12+,13+,14-,16-,17+,20+/m1/s1

Standard InChI Key:  VSRLMYQKLUPERI-JCQBEPMYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.6443  -24.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450  -22.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252  -22.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064  -24.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138  -23.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949  -23.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814  -24.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066  -24.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5581  -23.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3786  -24.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806  -24.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6940  -24.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709  -23.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737  -25.0399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4912  -24.2841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597  -22.7163    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685  -22.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9002  -25.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494  -25.4047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977  -22.7245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434  -25.4809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3596  -25.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647  -26.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648  -25.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6596  -27.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750  -27.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839  -25.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0801  -27.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0
  1  4  1  0
  9  2  1  0
  5  3  1  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 10 14  1  6
 12 15  2  0
  9 16  1  6
  3 17  1  6
  4 18  1  1
  1 19  1  6
  5 20  1  6
  8 21  2  0
 19 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 23 26  1  0
 11 27  1  1
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878114

   Microhelenin B

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 2.92

#Rotatable Bonds: 3

Polar Surface Area: 69.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: 3.13

References

1. Xue PH, Zhang N, Liu D, Zhang QR, Duan JS, Yu YQ, Li JY, Cao SJ, Zhao F, Kang N, Qiu F..  (2021)  Cytotoxic and Anti-Inflammatory Sesquiterpenes from the Whole Plants of Centipeda minima.,  84  (2.0): [PMID:33533247] [10.1021/acs.jnatprod.0c00884]

Source

Source(1):

• Scientific Literature