(-)-dehydrodiconiferyl alcohol

ID: ALA1761712

Chembl Id: CHEMBL1761712

Cas Number: 155836-29-6

PubChem CID: 11078843

Max Phase: Preclinical

Molecular Formula: C20H22O6

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Dehydrodiconiferyl Alcohol | (-)-Dehydrodiconiferyl Alcohol|155836-29-6|5-O-Methylhierochin D|(7R,8S)-dehydrodiconiferyl alcohol|CHEBI:70467|(-)-DCA|4-[(2R,3S)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol|CHEMBL1761712|DTXSID701107496|HY-N2682|(2R,3S)-dehydrodiconiferyl alcohol|AKOS040761186|FS-9216|(-)-(2R,3S)-dehydrodiconiferyl alcohol|7-Methoxy-5-[(E)-3-hydroxy-1-propenyl]-2beta-(3-methoxy-4-hydroxyphenyl)-2,3-dihydrobenzofuran-3aShow More⌵

Canonical SMILES:  COc1cc([C@@H]2Oc3c(OC)cc(/C=C/CO)cc3[C@H]2CO)ccc1O

Standard InChI:  InChI=1S/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+/t15-,19+/m1/s1

Standard InChI Key:  KUSXBOZNRPQEON-GWKPYITFSA-N

Alternative Forms

1. Parent:

   

   ALA1761712

   DEHYDROCONIFERYL ALCOHOL

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: 358.39

Molecular Weight (Monoisotopic): 358.1416

AlogP: 2.62

#Rotatable Bonds: 6

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.91

CX Basic pKa:

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: 1.98

References

1. 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]

2. 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]

3. Lou LL, Yao GD, Wang J, Zhao WY, Wang XB, Huang XX, Song SJ..  (2018)  Enantiomeric neolignans from Picrasma quassioides exhibit distinctive cytotoxicity on hepatic carcinoma cells through ROS generation and apoptosis induction.,  28  (8): [PMID:29567344] [10.1016/j.bmcl.2018.03.043]

Source

Source(1):

• Scientific Literature