Ostruthin

Details

• Internal ID: 8255e210-5027-4ca7-99f5-64b5f1a26006
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 6-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxychromen-2-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C=C2C(=C1)C=CC(=O)O2)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C=C2C(=C1)C=CC(=O)O2)O)/C)C
• InChI: InChI=1S/C19H22O3/c1-13(2)5-4-6-14(3)7-8-15-11-16-9-10-19(21)22-18(16)12-17(15)20/h5,7,9-12,20H,4,6,8H2,1-3H3/b14-7+
• InChI Key: INBMTJJPUABOQJ-VGOFMYFVSA-N
• Popularity: 60 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

• 148-83-4
• Ostruthine
• 6-Geranyl-7-hydroxycoumarin
• CHEBI:69833
• UNII-XHK3RR9BOR
• XHK3RR9BOR
• NSC83434
• CCRIS 8087
• NSC 83434
• NSC-83434
• 6-(3,7-Dimethyl-2,6-octadienyl)-7-hydroxycoumarin
• (E)-6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxycoumarin
• 6-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxy-chromen-2-one
• (E)-6-(3,7-Dimethyl-2,6-octadienyl)-7-hydroxy-2H-1-benzopyran-2-one
• 2H-1-Benzopyran-2-one, 6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)- (9CI)
• OSTRUTHIN [MI]
• MEGxp0_001198
• SCHEMBL2936116
• SCHEMBL2936121
• CHEMBL1812645
• ACon1_001218
• DTXSID601318569
• 6-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxychromen-2-one
• AKOS040735765
• 2H-1-BENZOPYRAN-2-ONE,6-[(2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL]-7-HYDROXY-
• C09281
• 6-(3,7-DIMETHYL-2,6-OCTADIENYL)UMBELLIFERONE
• 6-Geranyl-7-hydroxycoumarin, >=95% (LC/MS-ELSD)
• Q21547160
• Coumarin,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)-
• Coumarin, 6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)-
• Coumarin, 6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-,(E)-
• (E)-6-(3,7-dimethylocta-2,6-dien-1-yl)-7-hydroxy-2H-chromen-2-one
• 2H-1-Benzopyran-2-one,6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-,(E)-
• 2H-1-Benzopyran-2-one,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)-
• 2H-1-Benzopyran-2-one, 6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.8032	80.32%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6499	64.99%
OATP2B1 inhibitior	-	0.7178	71.78%
OATP1B1 inhibitior	+	0.9089	90.89%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8185	81.85%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8281	82.81%
CYP3A4 substrate	-	0.5601	56.01%
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	-	0.8227	82.27%
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	-	0.7626	76.26%
Skin irritation	-	0.7432	74.32%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8063	80.63%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.6938	69.38%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6380	63.80%
Acute Oral Toxicity (c)	III	0.4824	48.24%
Estrogen receptor binding	+	0.9077	90.77%
Androgen receptor binding	+	0.6275	62.75%
Thyroid receptor binding	+	0.6332	63.32%
Glucocorticoid receptor binding	+	0.8720	87.20%
Aromatase binding	+	0.7342	73.42%
PPAR gamma	+	0.9032	90.32%
Honey bee toxicity	-	0.9311	93.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
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	98.99%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.94%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.80%	92.08%
CHEMBL3401	O75469	Pregnane X receptor	94.71%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	93.34%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.95%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.18%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.15%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.04%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.45%	86.33%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.80%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.80%	94.00%

Plants that contains it

• Angelica decursiva
• Cirsium canum
• Flacourtia jangomas
• Hansenia weberbaueriana
• Luvunga sarmentosa
• Opuntia humifusa
• Pamburus missionis
• Peucedanum ostruthium
• Philotheca tomentella
• Piper hancei
• Salvia lasiantha

Cross-Links

• PubChem: 5281420
• NPASS: NPC243688
• ChEMBL: CHEMBL1812645
• LOTUS: LTS0125425
• wikiData: Q21547160