5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one

ID: ALA476121

Chembl Id: CHEMBL476121

Cas Number: 16545-23-6

PubChem CID: 73207

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(OC)c(O)c2c(=O)cc(-c3ccc(O)cc3)oc2c1OC

Standard InChI:  InChI=1S/C18H16O7/c1-22-16-14(21)13-11(20)8-12(9-4-6-10(19)7-5-9)25-15(13)17(23-2)18(16)24-3/h4-8,19,21H,1-3H3

Standard InChI Key:  SAMBWAJRKKEEOR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA476121

   XANTHOMICROL

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: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 98.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.27

CX Basic pKa:

CX LogP: 2.54

CX LogD: 2.48

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.35

References

1. Mercader AG, Duchowicz PR, Fernández FM, Castro EA, Bennardi DO, Autino JC, Romanelli GP..  (2008)  QSAR prediction of inhibition of aldose reductase for flavonoids.,  16  (15): [PMID:18585047] [10.1016/j.bmc.2008.06.004]

2. Oshitari T, Okuyama Y, Miyata Y, Kosano H, Takahashi H, Natsugari H..  (2011)  B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.,  19  (23): [PMID:22047798] [10.1016/j.bmc.2011.10.001]

3. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O.  (2012)  Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO,  21  (9): [10.1007/s00044-011-9767-1]

4. Miyata Y, Oshitari T, Okuyama Y, Shimada A, Takahashi H, Natsugari H, Kosano H..  (2013)  Polymethoxyflavones as agents that prevent formation of cataract: nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells.,  23  (1): [PMID:23199882] [10.1016/j.bmcl.2012.10.133]

5. Ruiu S, Anzani N, Orrù A, Floris C, Caboni P, Alcaro S, Maccioni E, Distinto S, Cottiglia F..  (2015)  Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.,  78  (1): [PMID:25562563] [10.1021/np500671v]

6. Almahmoud S, Elix CC, Jones JO, Hopkins CR, Vennerstrom JL, Zhong HA..  (2021)  Virtual screening and biological evaluation of PPARγ antagonists as potential anti-prostate cancer agents.,  46  [PMID:34433102] [10.1016/j.bmc.2021.116368]

7. Donadio G, Chini MG, Parisi V, Mensitieri F, Malafronte N, Bifulco G, Bisio A, De Tommasi N, Bader A..  (2022)  Diterpenoid Constituents of Psiadia punctulata and Evaluation of Their Antimicrobial Activity.,  85  (7.0): [PMID:35748331] [10.1021/acs.jnatprod.1c01093]

Source

Source(1):

• Scientific Literature