Isosteviol oxime

ID: ALA594630

Chembl Id: CHEMBL594630

PubChem CID: 46227077

Max Phase: Preclinical

Molecular Formula: C20H31NO3

Molecular Weight: 333.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isosteviol Oxime | Isosteviol oxime|CHEMBL594630

Canonical SMILES:  C[C@@]12CC[C@@H]3[C@@](CC[C@H]4[C@@]3(C)CCC[C@@]4(C)C(=O)O)(C/C1=N\O)C2

Standard InChI:  InChI=1S/C20H31NO3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21-24/h13-14,24H,4-12H2,1-3H3,(H,22,23)/b21-15+/t13-,14-,17-,18+,19+,20-/m0/s1

Standard InChI Key:  VAPPWLUSZRLUPV-AKWMADHGSA-N

Alternative Forms

1. Parent:

   

   ALA594630

   ISOSTEVIOL OXIME

Molecule Features

Natural Product: No

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: 333.47

Molecular Weight (Monoisotopic): 333.2304

AlogP: 4.70

#Rotatable Bonds: 1

Polar Surface Area: 69.89

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.57

CX Basic pKa: 1.79

CX LogP: 4.51

CX LogD: 1.76

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 2.70

References

1. Chang SF, Chou BH, Yang LM, Hsu FL, Lin WK, Ho Y, Lin SJ..  (2009)  Microbial transformation of isosteviol oxime and the inhibitory effects on NF-kappaB and AP-1 activation in LPS-stimulated macrophages.,  17  (17): [PMID:19648015] [10.1016/j.bmc.2009.07.029]

2. Chou BH, Yang LM, Chang SF, Hsu FL, Wang LH, Lin WK, Liu PC, Lin SJ..  (2011)  Transformation of isosteviol lactam by fungi and the suppressive effects of its transformed products on LPS-induced iNOS expression in macrophages.,  74  (6): [PMID:21598928] [10.1021/np100915q]

3. Ye N, Ding Y, Wild C, Shen Q, Zhou J..  (2014)  Small molecule inhibitors targeting activator protein 1 (AP-1).,  57  (16): [PMID:24831826] [10.1021/jm5004733]

4. Li N, Li X, Deng M, Zhu F, Wang Z, Sheng R, Wu W, Guo R..  (2023)  Isosteviol derivatives as protein tyrosine Phosphatase-1B inhibitors: Synthesis, biological evaluation and molecular docking.,  83  [PMID:36963270] [10.1016/j.bmc.2023.117240]

Source

Source(1):

• Scientific Literature