3-Hydroxy-6-methoxy-8,8-dimethyl-1-oxo-1,3,4,7,8,9-hexahydro-cyclopenta[h]isochromene-5-carbaldehyde

ID: ALA518277

Chembl Id: CHEMBL518277

PubChem CID: 25147702

Max Phase: Preclinical

Molecular Formula: C16H18O5

Molecular Weight: 290.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C=O)c2c(c3c1CC(C)(C)C3)C(=O)OC(O)C2

Standard InChI:  InChI=1S/C16H18O5/c1-16(2)5-9-10(6-16)14(20-3)11(7-17)8-4-12(18)21-15(19)13(8)9/h7,12,18H,4-6H2,1-3H3

Standard InChI Key:  PMLIQJUDZQZWIQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA518277

   3-Hydroxy-6-methoxy-8,8-dimethyl-1-oxo-1,3,4,7,8,9-hexahydro-cyclopenta[h]isochromene-5-carbaldehyde

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: 290.31

Molecular Weight (Monoisotopic): 290.1154

AlogP: 1.66

#Rotatable Bonds: 2

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.08

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.66

Np Likeness Score: 1.71

References

1. Ling Q, Huang Y, Zhou Y, Cai Z, Xiong B, Zhang Y, Ma L, Wang X, Li X, Li J, Shen J..  (2008)  Illudalic acid as a potential LAR inhibitor: synthesis, SAR, and preliminary studies on the mechanism of action.,  16  (15): [PMID:18579388] [10.1016/j.bmc.2008.06.014]

2. McCullough BS, Batsomboon P, Hutchinson KB, Dudley GB, Barrios AM..  (2019)  Synthesis and PTP Inhibitory Activity of Illudalic Acid and Its Methyl Ether, with Insights into Selectivity for LAR PTP over Other Tyrosine Phosphatases under Physiologically Relevant Conditions.,  82  (12): [PMID:31809044] [10.1021/acs.jnatprod.9b00663]

Source

Source(1):

• Scientific Literature