4-Hydroxyphenyl 6-O-[(3R)-3,4-dihydroxy-2-methylenebutanoyl]-beta-D-glucopyranoside

ID: ALA464544

Chembl Id: CHEMBL464544

PubChem CID: 10620152

Max Phase: Preclinical

Molecular Formula: C17H22O10

Molecular Weight: 386.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C(=O)OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O)[C@@H](O)CO

Standard InChI:  InChI=1S/C17H22O10/c1-8(11(20)6-18)16(24)25-7-12-13(21)14(22)15(23)17(27-12)26-10-4-2-9(19)3-5-10/h2-5,11-15,17-23H,1,6-7H2/t11-,12+,13+,14-,15+,17+/m0/s1

Standard InChI Key:  OGPNIAJZUFYDRF-MCDJNTACSA-N

Alternative Forms

1. Parent:

   

   ALA464544

   [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (3R)-3,4-dihydroxy-2-methylidenebutanoate

Molecule Features

Natural Product: Yes

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: 386.35

Molecular Weight (Monoisotopic): 386.1213

AlogP: -1.97

#Rotatable Bonds: 7

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.82

CX Basic pKa: ┄

CX LogP: -0.99

CX LogD: -0.99

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.23

Np Likeness Score: 2.13

References

1. Perry NB, Brennan NJ..  (1997)  Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.,  60  (6): [PMID:9214736] [10.1021/np970013z]

2. MacLeod JK, Rasmussen HB, Willis AC..  (1997)  A new glycoside antimicrobial agent from Persoonia linearis x pinifolia.,  60  (6): [PMID:9296952] [10.1021/np970006a]

Source

Source(1):

• Scientific Literature