Limocitrol

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	289317dd-45a3-41d4-8b16-0dd953306db8
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
IUPAC Name	3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxychromen-4-one
SMILES (Canonical)	COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O)O)O
SMILES (Isomeric)	COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O)O)O
InChI	InChI=1S/C18H16O9/c1-24-9-6-7(4-5-8(9)19)15-13(22)11(20)10-12(21)17(25-2)14(23)18(26-3)16(10)27-15/h4-6,19,21-23H,1-3H3
InChI Key	LCKHNFJHVWUHTR-UHFFFAOYSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₁₈H₁₆O₉
Molecular Weight	376.30 g/mol
Exact Mass	376.07943208 g/mol
Topological Polar Surface Area (TPSA)	135.00 Å²
XlogP	2.40
Atomic LogP (AlogP)	2.31
H-Bond Acceptor	9
H-Bond Donor	4
Rotatable Bonds	4

Synonyms

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549-10-0

113VHU3N34

UNII-113VHU3N34

3,5,7,4'-Tetrahydroxy-6,8,3'-trimethoxyflavone

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxychromen-4-one

3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-1-benzopyran-4-one

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one

CHEBI:168259

DTXSID301131225

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	+	0.5798	57.98%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.5546	55.46%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5651	56.51%
P-glycoprotein inhibitior	-	0.4947	49.47%
P-glycoprotein substrate	-	0.8460	84.60%
CYP3A4 substrate	+	0.5176	51.76%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6154	61.54%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5640	56.40%
CYP2D6 inhibition	-	0.7310	73.10%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	+	0.8275	82.75%
CYP inhibitory promiscuity	+	0.8068	80.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6142	61.42%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.6102	61.02%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	+	0.5772	57.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.7662	76.62%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7882	78.82%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.8898	88.98%
Androgen receptor binding	+	0.6960	69.60%
Thyroid receptor binding	+	0.6369	63.69%
Glucocorticoid receptor binding	+	0.8248	82.48%
Aromatase binding	+	0.6896	68.96%
PPAR gamma	+	0.7773	77.73%
Honey bee toxicity	-	0.9024	90.24%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.8724	87.24%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.72%	94.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	96.71%	98.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.69%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.71%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.07%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.77%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	88.29%	95.48%
CHEMBL2581	P07339	Cathepsin D	87.67%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.30%	99.17%
CHEMBL3194	P02766	Transthyretin	84.18%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.01%	99.23%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Baccharis magellanica

Beilschmiedia volckii

Chrysosplenium echinus

Cirsium nipponicum var. incomptum