erythro-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol

ID: ALA560169

Chembl Id: CHEMBL560169

Cas Number: 890317-92-7

PubChem CID: 21577856

Max Phase: Preclinical

Molecular Formula: C20H24O7

Molecular Weight: 376.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H](O)[C@@H](CO)Oc2ccc(/C=C/CO)cc2OC)ccc1O

Standard InChI:  InChI=1S/C20H24O7/c1-25-17-11-14(6-7-15(17)23)20(24)19(12-22)27-16-8-5-13(4-3-9-21)10-18(16)26-2/h3-8,10-11,19-24H,9,12H2,1-2H3/b4-3+/t19-,20+/m1/s1

Standard InChI Key:  FYEZJIXULOZDRT-WGLWSTOQSA-N

Alternative Forms

1. Parent:

   

   ALA560169

   (1S,2R)-1-(4-Hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-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: 376.41

Molecular Weight (Monoisotopic): 376.1522

AlogP: 1.89

#Rotatable Bonds: 9

Polar Surface Area: 108.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.91

CX Basic pKa:

CX LogP: 1.50

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 1.34

References

1. Mei RQ, Wang YH, Du GH, Liu GM, Zhang L, Cheng YX..  (2009)  Antioxidant Lignans from the Fruits of Broussonetia papyrifera.,  72  (4): [PMID:19296617] [10.1021/np800488p]

2. Jeong EJ, Cho JH, Sung SH, Kim SY, Kim YC..  (2011)  Inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophage cells by lignans isolated from Euonymus alatus leaves and twigs.,  21  (8): [PMID:21435874] [10.1016/j.bmcl.2011.02.102]

3. Cutillo F, D'Abrosca B, DellaGreca M, Fiorentino A, Zarrelli A..  (2003)  Lignans and neolignans from Brassica fruticulosa: effects on seed germination and plant growth.,  51  (21): [PMID:14518939] [10.1021/jf034644c]

Source

Source(1):

• Scientific Literature