Gardenin A

Details

• Internal ID: 9dcb78d0-f2a2-4600-808e-6c51d729021a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O
• InChI: InChI=1S/C21H22O9/c1-24-13-7-10(8-14(25-2)17(13)26-3)12-9-11(22)15-16(23)19(27-4)21(29-6)20(28-5)18(15)30-12/h7-9,23H,1-6H3
• InChI Key: MQBFFYQCZCKSBX-UHFFFAOYSA-N
• Popularity: 76 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.12638228 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• Gardenin
• 21187-73-5
• 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• 5-Hydroxy-3',4',5',6,7,8-hexamethoxyflavone
• 5OH3'4'5'6,7,8-hexMeO-Flavone
• 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• NSC94889
• NSC-94889
• 24J0W87Z43
• 4H-1-Benzopyran-4-one,5-hydroxy-6,7,8- trimethoxy-2-(3,4,5-trimethoxyphenyl)-
• 5-Hydroxy-6,7,8-trimethoxy-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
• 3',4',5',6,7,8-Hexamethoxy-5-hydroxyflavone
• Gardenin (1)
• gardenin a, AldrichCPR
• GARDENIN A [MI]
• MLS000863619
• BIDD:ER0415
• CHEMBL77705
• SPECTRUM1505146
• MEGxp0_001882
• SCHEMBL1764114
• UNII-24J0W87Z43
• ACon1_000048
• DTXSID30175417
• MQBFFYQCZCKSBX-UHFFFAOYSA-N
• BDBM153263
• HMS2269F21
• HY-N8303
• LMPK12111493
• MFCD00017419
• NSC 94889
• AKOS024286925
• Flavone,4',5',6,7,8-hexamethoxy-
• NCGC00096041-01
• NCGC00096041-02
• NCGC00168844-01
• NCI60_042113
• SMR000440777
• CS-0142854
• FT-0630469
• 5-Hydroxy-6,7,8,3',4',5'-Hexamethoxyflaone
• 5-hydroxy-6,7,8,3',4',5'-hexamethoxyflavone
• BRD-K78744675-001-01-7
• Q27253857
• 4H-1-Benzopyran-4-one,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)-
• 4H-1-Benzopyran-4-one, 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.7622	76.22%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	0.8651	86.51%
OATP1B1 inhibitior	+	0.9205	92.05%
OATP1B3 inhibitior	+	0.9817	98.17%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7185	71.85%
P-glycoprotein inhibitior	+	0.8524	85.24%
P-glycoprotein substrate	-	0.8684	86.84%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5748	57.48%
CYP2C9 inhibition	-	0.8861	88.61%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8530	85.30%
CYP2C8 inhibition	+	0.6179	61.79%
CYP inhibitory promiscuity	+	0.6103	61.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.6883	68.83%
Skin irritation	-	0.7150	71.50%
Skin corrosion	-	0.9836	98.36%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5379	53.79%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9504	95.04%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7171	71.71%
Acute Oral Toxicity (c)	II	0.4982	49.82%
Estrogen receptor binding	+	0.8777	87.77%
Androgen receptor binding	+	0.7004	70.04%
Thyroid receptor binding	+	0.7038	70.38%
Glucocorticoid receptor binding	+	0.7394	73.94%
Aromatase binding	+	0.7111	71.11%
PPAR gamma	+	0.7245	72.45%
Honey bee toxicity	-	0.7865	78.65%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.8902	89.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	11220.2 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.81%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.84%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.18%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.47%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.17%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.08%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.36%	98.95%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	86.60%	98.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.30%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.95%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.62%	93.99%
CHEMBL3194	P02766	Transthyretin	81.64%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.49%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.17%	94.45%

Plants that contains it

• Gardenia jasminoides
• Gardenia resinifera
• Murraya paniculata
• Polygala chinensis
• Rhamnus japonica
• Salvia mirzayanii
• Tamarix dioica

Cross-Links

• PubChem: 261859
• NPASS: NPC250822
• ChEMBL: CHEMBL77705
• LOTUS: LTS0151938
• wikiData: Q27253857