Osthenol

Details

• Internal ID: ac0d412b-30b7-467f-8474-f1be30b4c49c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-8-(3-methylbut-2-enyl)chromen-2-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC(=O)C=C2)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1OC(=O)C=C2)O)C
• InChI: InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3
• InChI Key: RAKJVIPCCGXHHS-UHFFFAOYSA-N
• Popularity: 84 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.26 g/mol
• Exact Mass: 230.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 484-14-0
• 7-hydroxy-8-(3-methylbut-2-enyl)chromen-2-one
• 7-hydroxy-8-prenylcoumarin
• 7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one
• UNII-7X6RF2708X
• CHEMBL350475
• 2H-1-Benzopyran-2-one, 7-hydroxy-8-(3-methyl-2-butenyl)-
• CHEBI:81485
• 7X6RF2708X
• NSC-625328
• 7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
• 7-Hydroxy-8-prenylcoumarin; NSC 625328
• 8-prenylumbelliferone
• SCHEMBL51013
• MEGxp0_000219
• ACon1_000810
• DTXSID80197508
• BCP24741
• HY-N2554
• 7-hydroxy--2H-1-benzopyran-2-one
• BDBM50240868
• MFCD03427690
• NSC625328
• AKOS025402390
• AC-8807
• 8-(3-methylbut-2-en-1-yl)umbelliferone
• MS-23307
• NCI60_007807
• 7-HYDROXY-8-ISOPENT-2-ENYLCOUMARIN
• 7-hydroxy-8-(3-methyl-but-2-enyl)coumarin
• CS-0022826
• FT-0777401
• C18080
• 7-Hydroxy-8-(3-methyl-but-2-enyl)-chromen-2-one
• BRD-K53399718-001-01-8
• COUMARIN, 7-HYDROXY-8-(3-METHYL-2-BUTENYL)-
• Q27155413
• 7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.7083	70.83%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7963	79.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5729	57.29%
P-glycoprotein inhibitior	-	0.8281	82.81%
P-glycoprotein substrate	-	0.9489	94.89%
CYP3A4 substrate	-	0.6598	65.98%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.8258	82.58%
CYP3A4 inhibition	-	0.8789	87.89%
CYP2C9 inhibition	+	0.7537	75.37%
CYP2C19 inhibition	+	0.7529	75.29%
CYP2D6 inhibition	-	0.8050	80.50%
CYP1A2 inhibition	+	0.6859	68.59%
CYP2C8 inhibition	-	0.9144	91.44%
CYP inhibitory promiscuity	+	0.7015	70.15%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6850	68.50%
Eye corrosion	-	0.9877	98.77%
Eye irritation	+	0.8172	81.72%
Skin irritation	-	0.6251	62.51%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6261	62.61%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.6003	60.03%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5732	57.32%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	+	0.8762	87.62%
Androgen receptor binding	+	0.6910	69.10%
Thyroid receptor binding	+	0.6509	65.09%
Glucocorticoid receptor binding	+	0.9028	90.28%
Aromatase binding	+	0.8107	81.07%
PPAR gamma	+	0.8539	85.39%
Honey bee toxicity	-	0.9395	93.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	260 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.87%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.79%	94.73%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.56%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.78%	95.56%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.31%	91.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.00%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.91%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.90%	96.95%

Plants that contains it

• Angelica dahurica
• Angelica dahurica var. formosana
• Angelica keiskei
• Angelica pubescens
• Citrus × aurantium
• Citrus lucida
• Citrus medica
• Ferulago aucherii
• Hansenia weberbaueriana
• Haplophyllum patavinum
• Heracleum candicans
• Juniperus chinensis
• Lysimachia arvensis
• Melicope semecarpifolia
• Ostericum grossiserratum
• Phellodendron amurense
• Prangos ferulacea
• Prangos uloptera
• Rosa transmorrisonensis
• Uncaria perrottetii
• Zanthoxylum beecheyanum

Cross-Links

• PubChem: 5320318
• NPASS: NPC244495
• ChEMBL: CHEMBL350475
• LOTUS: LTS0259150
• wikiData: Q27155413