ID: ALA477544

Max Phase: Preclinical

Molecular Formula: C20H30O4

Molecular Weight: 334.46

Molecule Type: Small molecule

Representations

Synonyms (1): 7-Beta-Hydroxyisosteviol
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@@]12CC[C@H]3[C@]4(C)CCC[C@@](C)(C(=O)O)[C@H]4C[C@H](O)[C@]3(CC1=O)C2

Standard InChI:  InChI=1S/C20H30O4/c1-17-8-5-12-18(2)6-4-7-19(3,16(23)24)13(18)9-14(21)20(12,11-17)10-15(17)22/h12-14,21H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,17-,18-,19+,20+/m0/s1

Standard InChI Key:  RARHTOIMTZCWKS-SWTLLTDLSA-N

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

Properties

Molecular Weight: 334.46

Molecular Weight (Monoisotopic): 334.2144

AlogP: 3.41

#Rotatable Bonds: 1

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.53

CX Basic pKa:

CX LogP: 3.27

CX LogD: 0.49

Aromatic Rings: 0

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: 3.21

References

1. Akihisa T, Hamasaki Y, Tokuda H, Ukiya M, Kimura Y, Nishino H..  (2004)  Microbial transformation of isosteviol and inhibitory effects on Epstein-Barr virus activation of the transformation products.,  67  (3): [PMID:15043419] [10.1021/np030393q]

2. Wonganan O, Tocharus C, Puedsing C, Homvisasevongsa S, Sukcharoen O, Suksamrarn A..  (2013)  Potent vasorelaxant analogs from chemical modification and biotransformation of isosteviol.,  62  [PMID:23466565] [10.1016/j.ejmech.2013.01.022]

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]

Source

Source(1):

• Scientific Literature