(3R,4S,7S,8R)-6-((E)-(4R,5R,6R,6aS,9S,10aR)-5-Hydroxy-3-isopropyl-9-methoxymethyl-6,10a-dimethyl-1,2,4,5,6,6a,7,8,9,10a-decahydro-dicyclopenta[a,d]cycloocten-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

ID: ALA4218471

Chembl Id: CHEMBL4218471

PubChem CID: 101410224

Max Phase: Preclinical

Molecular Formula: C30H48O8

Molecular Weight: 536.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@H]1CC[C@@H]2/C1=C\[C@@]1(C)CCC(C(C)C)=C1[C@@H](O[C@H]1O[C@@H]3COC(C)(C)O[C@H]3[C@H](O)[C@H]1O)[C@H](O)[C@@H]2C

Standard InChI:  InChI=1S/C30H48O8/c1-15(2)18-10-11-30(6)12-20-17(13-34-7)8-9-19(20)16(3)23(31)27(22(18)30)37-28-25(33)24(32)26-21(36-28)14-35-29(4,5)38-26/h12,15-17,19,21,23-28,31-33H,8-11,13-14H2,1-7H3/b20-12-/t16-,17-,19+,21-,23-,24-,25-,26-,27-,28-,30-/m1/s1

Standard InChI Key:  LOAPHXVWCJVEPY-XXUMMOLISA-N

Alternative Forms

1. Parent:

   

   ALA4218471

   (4aR,6S,7R,8R,8aS)-6-[[(1E,3R,8R,9R,10R,11S,14S)-9-hydroxy-14-(methoxymethyl)-3,10-dimethyl-6-propan-2-yl-8-tricyclo[9.3.0.03,7]tetradeca-1,6-dienyl]oxy]-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

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: 536.71

Molecular Weight (Monoisotopic): 536.3349

AlogP: 3.33

#Rotatable Bonds: 5

Polar Surface Area: 106.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.26

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.46

Np Likeness Score: 2.07

References

1. Inoue T, Higuchi Y, Yoneyama T, Lin B, Nunomura K, Honma Y, Kato N..  (2018)  Semisynthesis and biological evaluation of a cotylenin A mimic derived from fusicoccin A.,  28  (4): [PMID:29398541] [10.1016/j.bmcl.2018.01.030]

2. Ogino N, Masuda R, Lynn Punzalan L, Yamashita E, Igaue S, Inoue Y, Ohkanda J..  (2022)  Structure-activity-relationship study of semi-synthetically modified fusicoccins on their stabilization effect for 14-3-3-phospholigand interactions.,  73  [PMID:36182801] [10.1016/j.bmc.2022.117020]

Source

Source(1):

• Scientific Literature