8-Geranylumbelliferone

Details

• Internal ID: a81bf09d-9cec-460b-b4f2-705cbc94e213
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 8-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxychromen-2-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C=CC2=C1OC(=O)C=C2)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C=CC2=C1OC(=O)C=C2)O)/C)C
• InChI: InChI=1S/C19H22O3/c1-13(2)5-4-6-14(3)7-10-16-17(20)11-8-15-9-12-18(21)22-19(15)16/h5,7-9,11-12,20H,4,6,10H2,1-3H3/b14-7+
• InChI Key: QPMKRRUDQIKGNH-VGOFMYFVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 8-geranyl-7-hydroxycoumarin
• 23660-05-1
• 8-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxychromen-2-one
• 2H-1-Benzopyran-2-one, 8-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-7-hydroxy-
• SCHEMBL24075636
• CHEBI:134358
• DTXSID201151248
• AKOS040735253
• C21495
• EN300-21995970
• 7-Hydroxy-8-(3,7-dimethyl-2,6-octadienyl)-2H-1-benzopyran-2-one
• 8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-2H-chromen-2-one
• 8-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-7-hydroxy-2H-1-benzopyran-2-one
• 8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-2H-1-benzopyran-2-one
• NCGC00384605-01!8-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxychromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.5165	51.65%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6499	64.99%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8919	89.19%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8691	86.91%
P-glycoprotein inhibitior	-	0.6277	62.77%
P-glycoprotein substrate	-	0.9295	92.95%
CYP3A4 substrate	-	0.5758	57.58%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.8258	82.58%
CYP3A4 inhibition	-	0.7481	74.81%
CYP2C9 inhibition	+	0.5297	52.97%
CYP2C19 inhibition	+	0.7361	73.61%
CYP2D6 inhibition	-	0.8344	83.44%
CYP1A2 inhibition	+	0.8376	83.76%
CYP2C8 inhibition	-	0.8277	82.77%
CYP inhibitory promiscuity	-	0.5915	59.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7298	72.98%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.6275	62.75%
Skin irritation	-	0.7432	74.32%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7220	72.20%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6938	69.38%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6398	63.98%
Acute Oral Toxicity (c)	III	0.4824	48.24%
Estrogen receptor binding	+	0.8374	83.74%
Androgen receptor binding	+	0.7283	72.83%
Thyroid receptor binding	+	0.6206	62.06%
Glucocorticoid receptor binding	+	0.8683	86.83%
Aromatase binding	+	0.5889	58.89%
PPAR gamma	+	0.9090	90.90%
Honey bee toxicity	-	0.9144	91.44%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	97.04%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.29%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.88%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	92.64%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	91.00%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.89%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.83%	95.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.04%	92.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.83%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.30%	96.95%

Plants that contains it

• Atalantia buxifolia
• Boronia inornata
• Boronia lanceolata
• Luvunga sarmentosa
• Pamburus missionis
• Philotheca tomentella

Cross-Links

• PubChem: 71694409
• NPASS: NPC246694
• LOTUS: LTS0085632
• wikiData: Q74417338