Peucedanin

Details

• Internal ID: 1b814049-3922-4322-ac79-839853fc6277
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 3-methoxy-2-propan-2-ylfuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)C1=C(C2=C(O1)C=C3C(=C2)C=CC(=O)O3)OC
• SMILES (Isomeric): CC(C)C1=C(C2=C(O1)C=C3C(=C2)C=CC(=O)O3)OC
• InChI: InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3
• InChI Key: YQBNJPACAUPNLV-UHFFFAOYSA-N
• Popularity: 100 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 48.70 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 133-26-6
• Oreoselone methyl ether
• Peutsedin
• 4-Methoxy-5-isopropylfuro(2,3:6,7)coumarin
• BRN 0234473
• 3-methoxy-2-propan-2-ylfuro[3,2-g]chromen-7-one
• 3-Methoxy-2-(1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one
• UNII-N021633LOB
• CHEBI:8034
• N021633LOB
• 6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid delta-lactone
• 2-isopropyl-3-methoxy-7H-furo[3,2-g]chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 3-methoxy-2-(1-methylethyl)-
• 5-Benzofuranacrylic acid, 6-hydroxy-2-isopropyl-3-methoxy-, delta-lactone
• 5-19-06-00042 (Beilstein Handbook Reference)
• 3-methoxy-2-(propan-2-yl)-7H-furo[3,2-g]chromen-7-one
• 7H-FURO(3,2-g)(1)BENZOPYRAN-7-ONE, 2-ISOPROPYL-3-METHOXY-
• 3-Methoxy-2-(1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• Spectrum_001546
• PEUCEDANIN [MI]
• SpecPlus_000952
• Spectrum2_000729
• Spectrum3_001647
• Spectrum4_001666
• Spectrum5_000571
• Oprea1_190644
• Oprea1_837278
• BSPBio_003373
• KBioGR_002191
• KBioSS_002026
• MLS001049116
• DivK1c_007048
• SPECTRUM1504168
• SPBio_000658
• MEGxp0_001552
• SCHEMBL2249089
• CHEMBL1410943
• KBio1_001992
• KBio2_002026
• KBio2_004594
• KBio2_007162
• KBio3_002593
• YQBNJPACAUPNLV-UHFFFAOYSA-
• DTXSID10157897
• HMS2675C08
• CCG-40070
• STK396320
• AKOS000278122
• SDCCGMLS-0066802.P001
• NCGC00095695-01
• NCGC00095695-02
• LS-70731
• SMR000102964
• CL-381982
• C09283
• AB00053108-02
• 2-isopropyl-3-methoxy-furo[3,2-g]chromen-7-one
• BRD-K72034655-001-02-1
• Q27107645
• 7H-Furo3,2-g1benzopyran-7-one, 3-methoxy-2-(1-methylethyl)-
• 6-HYDROXY-2-ISOPROPYL-3-METHOXY-5-BENZOFURANACRYLIC ACID .GAMMA.-LACTONE
• InChI=1/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	+	0.8749	87.49%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6856	68.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6827	68.27%
P-glycoprotein inhibitior	-	0.5927	59.27%
P-glycoprotein substrate	-	0.7766	77.66%
CYP3A4 substrate	-	0.5833	58.33%
CYP2C9 substrate	-	0.6914	69.14%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.5461	54.61%
CYP2C9 inhibition	-	0.7410	74.10%
CYP2C19 inhibition	+	0.8823	88.23%
CYP2D6 inhibition	-	0.5509	55.09%
CYP1A2 inhibition	+	0.9326	93.26%
CYP2C8 inhibition	-	0.8315	83.15%
CYP inhibitory promiscuity	+	0.7482	74.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.3768	37.68%
Eye corrosion	-	0.9742	97.42%
Eye irritation	-	0.9252	92.52%
Skin irritation	-	0.7961	79.61%
Skin corrosion	-	0.9819	98.19%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7519	75.19%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.5052	50.52%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6712	67.12%
Acute Oral Toxicity (c)	II	0.5448	54.48%
Estrogen receptor binding	+	0.8629	86.29%
Androgen receptor binding	+	0.7689	76.89%
Thyroid receptor binding	+	0.6489	64.89%
Glucocorticoid receptor binding	+	0.5590	55.90%
Aromatase binding	+	0.8172	81.72%
PPAR gamma	+	0.6381	63.81%
Honey bee toxicity	-	0.8481	84.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9630	96.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2818.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.94%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.69%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.02%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.84%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.61%	90.71%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.73%	94.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.37%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.27%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.12%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.89%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.79%	96.00%

Plants that contains it

• Angelica decursiva
• Daucus carota
• Lythrum salicaria
• Myrrhis odorata
• Opopanax hispidus
• Peucedanum officinale
• Peucedanum tauricum
• Phaseolus vulgaris
• Prangos pabularia

Cross-Links

• PubChem: 8616
• NPASS: NPC98028
• ChEMBL: CHEMBL1410943
• LOTUS: LTS0016280
• wikiData: Q27107645