(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-6-((R)-4-(2,4-dihydroxyphenyl)butan-2-yloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3100130

PubChem CID: 71768559

Max Phase: Preclinical

Molecular Formula: C22H34O13

Molecular Weight: 506.50

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  C[C@H](CCc1ccc(O)cc1O)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H34O13/c1-9(2-3-10-4-5-11(25)6-12(10)26)32-21-19(31)17(29)20(14(8-24)34-21)35-22-18(30)16(28)15(27)13(7-23)33-22/h4-6,9,13-31H,2-3,7-8H2,1H3/t9-,13-,14-,15-,16+,17-,18-,19-,20-,21-,22+/m1/s1

Standard InChI Key:  ZRDADUROYMLJRH-DMISBUROSA-N

Molfile:  

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M  END

Associated Targets(Human)

TYR Tclin Tyrosinase (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

PPO2 Tyrosinase (3884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 506.50Molecular Weight (Monoisotopic): 506.1999AlogP: -2.94#Rotatable Bonds: 9
Polar Surface Area: 218.99Molecular Species: NEUTRALHBA: 13HBD: 9
#RO5 Violations: 3HBA (Lipinski): 13HBD (Lipinski): 9#RO5 Violations (Lipinski): 3
CX Acidic pKa: 9.54CX Basic pKa: CX LogP: -1.79CX LogD: -1.80
Aromatic Rings: 1Heavy Atoms: 35QED Weighted: 0.16Np Likeness Score: 1.75

References

1. Iwadate T, Kashiwakura Y, Masuoka N, Yamada Y, Nihei K..  (2014)  Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.,  24  (1): [PMID:24332496] [10.1016/j.bmcl.2013.11.063]
2. Iwadate T, Nihei K..  (2015)  Rhododendrol glycosides as stereospecific tyrosinase inhibitors.,  23  (20): [PMID:26386819] [10.1016/j.bmc.2015.09.014]

Source