3-(4-hydroxy-3-methoxyphenethyl)-5-methoxyphenol

ID: ALA219553

Chembl Id: CHEMBL219553

Cas Number: 83088-28-2

PubChem CID: 10221179

Max Phase: Preclinical

Molecular Formula: C16H18O4

Molecular Weight: 274.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Gigantol | 83088-28-2|3',4-dihydroxy-3,5'-dimethoxybibenzyl|Phenol, 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-|CHEMBL219553|DTXSID101287414|BDBM50346823|HY-N10549|CS-0610782|NS00097428|E88569|4-(3-Hydroxy-5-methoxyphenethyl)-2-methoxyphenol|4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol|NCGC00386002-01!4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

Canonical SMILES:  COc1cc(O)cc(CCc2ccc(O)c(OC)c2)c1

Standard InChI:  InChI=1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-15(18)16(9-11)20-2/h5-10,17-18H,3-4H2,1-2H3

Standard InChI Key:  BMSPEISBKGSBTR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA219553

   GIGANTOL

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: 274.32

Molecular Weight (Monoisotopic): 274.1205

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.50

CX Basic pKa:

CX LogP: 3.59

CX LogD: 3.58

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.88

Np Likeness Score: 0.81

References

1. Zhang X, Xu JK, Wang J, Wang NL, Kurihara H, Kitanaka S, Yao XS..  (2007)  Bioactive bibenzyl derivatives and fluorenones from Dendrobium nobile.,  70  (1): [PMID:17253844] [10.1021/np060449r]

2. Hernández-Romero Y, Rojas JI, Castillo R, Rojas A, Mata R..  (2004)  Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii.,  67  (2): [PMID:14987052] [10.1021/np030303h]

3. Hwang JS, Lee SA, Hong SS, Han XH, Lee C, Kang SJ, Lee D, Kim Y, Hong JT, Lee MK, Hwang BY..  (2010)  Phenanthrenes from Dendrobium nobile and their inhibition of the LPS-induced production of nitric oxide in macrophage RAW 264.7 cells.,  20  (12): [PMID:20483604] [10.1016/j.bmcl.2010.04.054]

4. Reyes-Ramírez A, Leyte-Lugo M, Figueroa M, Serrano-Alba T, González-Andrade M, Mata R..  (2011)  Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors.,  46  (7): [PMID:21514702] [10.1016/j.ejmech.2011.03.057]

5. Xu FQ, Xu FC, Hou B, Fan WW, Zi CT, Li Y, Dong FW, Liu YQ, Sheng J, Zuo ZL, Hu JM..  (2014)  Cytotoxic bibenzyl dimers from the stems of Dendrobium fimbriatum Hook.,  24  (22): [PMID:25316316] [10.1016/j.bmcl.2014.09.052]

6. Charoenrungruang S, Chanvorachote P, Sritularak B, Pongrakhananon V..  (2014)  Gigantol, a bibenzyl from Dendrobium draconis, inhibits the migratory behavior of non-small cell lung cancer cells.,  77  (6): [PMID:24844664] [10.1021/np500015v]

7. Zhou XM, Zheng CJ, Gan LS, Chen GY, Zhang XP, Song XP, Li GN, Sun CG..  (2016)  Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile.,  79  (7): [PMID:27310249] [10.1021/acs.jnatprod.6b00252]

8. Lin CW, Hwang TL, Chen FA, Huang CH, Hung HY, Wu TS..  (2016)  Chemical Constituents of the Rhizomes of Bletilla formosana and Their Potential Anti-inflammatory Activity.,  79  (8): [PMID:27525452] [10.1021/acs.jnatprod.6b00118]

9. Sheng Y, Chen Y, Zeng Z, Wu W, Wang J, Ma Y, Lin Y, Zhang J, Huang Y, Li W, Zhu Q, Wei X, Li S, Wisanwattana W, Li F, Liu W, Suksamrarn A, Zhang G, Jiao W, Wang F..  (2022)  Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming.,  65  (1.0): [PMID:34931827] [10.1021/acs.jmedchem.1c01605]

10. He L, Su Q, Bai L, Li M, Liu J, Liu X, Zhang C, Jiang Z, He J, Shi J, Huang S, Guo L..  (2020)  Recent research progress on natural small molecule bibenzyls and its derivatives in Dendrobium species.,  204  [PMID:32711292] [10.1016/j.ejmech.2020.112530]

Source

Source(1):

• Scientific Literature