longikaurin A

ID: ALA3823566

Chembl Id: CHEMBL3823566

PubChem CID: 102117144

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)[C@]23[C@H](O)[C@H]1CC[C@H]2[C@]12CCCC(C)(C)[C@H]1[C@H](O)[C@@]3(O)OC2

Standard InChI:  InChI=1S/C20H28O5/c1-10-11-5-6-12-18-8-4-7-17(2,3)13(18)16(23)20(24,25-9-18)19(12,14(10)21)15(11)22/h11-13,15-16,22-24H,1,4-9H2,2-3H3/t11-,12-,13+,15+,16-,18+,19-,20+/m0/s1

Standard InChI Key:  PSVHVXLCVSKJGM-MHRDNBEJSA-N

Alternative Forms

1. Parent:

   

   ALA3823566

   (1R,2S,5S,8R,9S,10S,11R,18R)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

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: 1.40

#Rotatable Bonds: ┄

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: 3.85

References

1. Xu S, Luo S, Yao H, Cai H, Miao X, Wu F, Yang DH, Wu X, Xie W, Yao H, Chen ZS, Xu J..  (2016)  Probing the Anticancer Action of Oridonin with Fluorescent Analogues: Visualizing Subcellular Localization to Mitochondria.,  59  (10): [PMID:27089099] [10.1021/acs.jmedchem.6b00408]

2. Yao H, Xie S, Ma X, Liu J, Wu H, Lin A, Yao H, Li D, Xu S, Yang DH, Chen ZS, Xu J..  (2020)  Identification of a Potent Oridonin Analogue for Treatment of Triple-Negative Breast Cancer.,  63  (15): [PMID:32610904] [10.1021/acs.jmedchem.0c00408]

3. Liu J, Xie S, Shao X, Xue S, Du P, Wu H, Xu S, Chen ZS, Yang DH, Xu J, Yao H..  (2022)  Identification of new potent anticancer derivatives through simplifying the core structure and modification on their 14- hydroxyl group from oridonin.,  231  [PMID:35121201] [10.1016/j.ejmech.2022.114155]

Source

Source(1):

• Scientific Literature