Graveoline

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	3154ab7b-e0c8-4ffb-990c-192cde8a37bb
Taxonomy	Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
IUPAC Name	2-(1,3-benzodioxol-5-yl)-1-methylquinolin-4-one
SMILES (Canonical)	CN1C2=CC=CC=C2C(=O)C=C1C3=CC4=C(C=C3)OCO4
SMILES (Isomeric)	CN1C2=CC=CC=C2C(=O)C=C1C3=CC4=C(C=C3)OCO4
InChI	InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3
InChI Key	COBBNRKBTCBWQP-UHFFFAOYSA-N
Popularity	70 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₇H₁₃NO₃
Molecular Weight	279.29 g/mol
Exact Mass	279.08954328 g/mol
Topological Polar Surface Area (TPSA)	38.80 Å²
XlogP	3.10
Atomic LogP (AlogP)	2.93
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	1

Synonyms

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485-61-0

2-(benzo[d][1,3]dioxol-5-yl)-1-methylquinolin-4(1H)-one

Graveolin

Foliosine

Rutamine

2-(1,3-benzodioxol-5-yl)-1-methylquinolin-4-one

CHEBI:5541

Alkaloid from Ruta angustifolia plant

NSC603064

Prestwick_165

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	+	0.9885	98.85%
Caco-2	+	0.8880	88.80%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6939	69.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9595	95.95%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8598	85.98%
BSEP inhibitior	+	0.7143	71.43%
P-glycoprotein inhibitior	-	0.4309	43.09%
P-glycoprotein substrate	-	0.9067	90.67%
CYP3A4 substrate	+	0.5457	54.57%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9485	94.85%
CYP2C8 inhibition	-	0.9179	91.79%
CYP inhibitory promiscuity	+	0.8557	85.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4113	41.13%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.7652	76.52%
Skin irritation	-	0.7863	78.63%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4468	44.68%
Micronuclear	+	0.7874	78.74%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8535	85.35%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5660	56.60%
Acute Oral Toxicity (c)	III	0.7156	71.56%
Estrogen receptor binding	+	0.8960	89.60%
Androgen receptor binding	+	0.8627	86.27%
Thyroid receptor binding	+	0.7475	74.75%
Glucocorticoid receptor binding	+	0.8555	85.55%
Aromatase binding	+	0.6760	67.60%
PPAR gamma	+	0.7272	72.72%
Honey bee toxicity	-	0.9015	90.15%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7317	73.17%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	15848.9 nM 39810.7 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	5011.87 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	1995.26 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	1584.89 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	10000 nM 10000 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	7943.3 nM 7943.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	3162.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.94%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.82%	96.77%
CHEMBL240	Q12809	HERG	95.72%	89.76%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.66%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.14%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.67%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.53%	93.99%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.63%	80.96%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.59%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	86.47%	94.73%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	85.10%	93.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.96%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.91%	93.40%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.04%	93.65%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.39%	96.25%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.51%	85.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.06%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.75%	92.62%

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.

Apium graveolens

Haplophyllum griffithianum