4-Geranyl-5-hydroxy-2(3h)-benzofuranone

Details

• Internal ID: 865611df-d51b-465a-83fb-90028b641732
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 4-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-hydroxy-3H-1-benzofuran-2-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C=CC2=C1CC(=O)O2)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C=CC2=C1CC(=O)O2)O)/C)C
• InChI: InChI=1S/C18H22O3/c1-12(2)5-4-6-13(3)7-8-14-15-11-18(20)21-17(15)10-9-16(14)19/h5,7,9-10,19H,4,6,8,11H2,1-3H3/b13-7+
• InChI Key: MYBGKXOIMVEVRQ-NTUHNPAUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.40 g/mol
• Exact Mass: 286.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• InChI=1/C18H22O3/c1-12(2)5-4-6-13(3)7-8-14-15-11-18(20)21-17(15)10-9-16(14)19/h5,7,9-10,19H,4,6,8,11H2,1-3H3/b13-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.5846	58.46%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7883	78.83%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.8943	89.43%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7718	77.18%
P-glycoprotein inhibitior	-	0.7970	79.70%
P-glycoprotein substrate	-	0.9378	93.78%
CYP3A4 substrate	-	0.5304	53.04%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.7855	78.55%
CYP3A4 inhibition	+	0.6425	64.25%
CYP2C9 inhibition	-	0.6375	63.75%
CYP2C19 inhibition	+	0.5744	57.44%
CYP2D6 inhibition	-	0.8696	86.96%
CYP1A2 inhibition	+	0.8499	84.99%
CYP2C8 inhibition	-	0.8576	85.76%
CYP inhibitory promiscuity	+	0.5880	58.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6351	63.51%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.5876	58.76%
Skin irritation	-	0.6852	68.52%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6517	65.17%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.6173	61.73%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5411	54.11%
Acute Oral Toxicity (c)	III	0.3856	38.56%
Estrogen receptor binding	+	0.8010	80.10%
Androgen receptor binding	+	0.6723	67.23%
Thyroid receptor binding	-	0.4880	48.80%
Glucocorticoid receptor binding	+	0.7659	76.59%
Aromatase binding	-	0.5570	55.70%
PPAR gamma	+	0.8464	84.64%
Honey bee toxicity	-	0.9321	93.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

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	99.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.50%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	92.43%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.91%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	91.85%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.57%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.71%	99.23%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.33%	85.30%
CHEMBL4208	P20618	Proteasome component C5	82.69%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.75%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.17%	96.09%

Plants that contains it

• Diplacus clevelandii

Cross-Links

• PubChem: 5324641
• LOTUS: LTS0060430
• wikiData: Q105174764