(+)-threo-guaiacylglycerol-beta-O-4'-sinapyl ether

ID: ALA2268766

Chembl Id: CHEMBL2268766

PubChem CID: 76326750

Max Phase: Preclinical

Molecular Formula: C21H26O8

Molecular Weight: 406.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H](O)[C@@H](CO)Oc2c(OC)cc(/C=C/CO)cc2OC)ccc1O

Standard InChI:  InChI=1S/C21H26O8/c1-26-16-11-14(6-7-15(16)24)20(25)19(12-23)29-21-17(27-2)9-13(5-4-8-22)10-18(21)28-3/h4-7,9-11,19-20,22-25H,8,12H2,1-3H3/b5-4+/t19-,20-/m1/s1

Standard InChI Key:  JVQPMSYMHZSFNV-WEPWYQGCSA-N

Alternative Forms

1. Parent:

   

   ALA2268766

   (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]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: 406.43

Molecular Weight (Monoisotopic): 406.1628

AlogP: 1.90

#Rotatable Bonds: 10

Polar Surface Area: 117.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.91

CX Basic pKa:

CX LogP: 1.35

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 1.42

References

1. 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]

2. Woo KW, Suh WS, Subedi L, Kim SY, Kim A, Lee KR..  (2016)  Bioactive lignan derivatives from the stems of Firmiana simplex.,  26  (3): [PMID:26774654] [10.1016/j.bmcl.2016.01.008]

Source

Source(1):

• Scientific Literature