Oxypseucedanin

Details

• Internal ID: 3c6146bd-b620-4065-be32-8e5865cd24fa
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 4-[[(2S)-3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one
• SMILES (Canonical): CC1(C(O1)COC2=C3C=CC(=O)OC3=CC4=C2C=CO4)C
• SMILES (Isomeric): CC1([C@@H](O1)COC2=C3C=CC(=O)OC3=CC4=C2C=CO4)C
• InChI: InChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3/t13-/m0/s1
• InChI Key: QTAGQHZOLRFCBU-ZDUSSCGKSA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 61.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 26091-73-6
• Oxypseucedanin
• (-)-Oxypeucedanin
• CCRIS 5725
• CHEBI:69830
• 4-[[(2S)-3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one
• S1Y67F37PI
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-, (S-)-
• 7H-FURO(3,2-g)(1)BENZOPYRAN-7-ONE, 4-(2,3-EPOXY-3-METHYLBUTOXY)-, (S)-(-)-
• 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3,3-dimethyloxiranyl)methoxy]-,(S)-
• (?)-Oxypeucedanine
• UNII-S1Y67F37PI
• OXYPEUCEDANIN, (S)-
• OXYPEUCEDANIN, (-)-
• CHEMBL510120
• (S)-(-)-OXYPEUCEDANIN
• DTXSID70948965
• BDBM50361376
• AKOS037515166
• LS-70720
• XO167943
• C09282
• Q27104977
• 4-[(3,3-Dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one
• 4-(((2S)-3,3-DIMETHYL-2-OXIRANYL)METHOXY)-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE
• 4-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g][1]benzopyran-7-one
• 7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 4-(((2S)-3,3-DIMETHYL-2-OXIRANYL)METHOXY)-
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-, (S-)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	+	0.7814	78.14%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7140	71.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	+	0.9063	90.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6840	68.40%
P-glycoprotein inhibitior	-	0.6556	65.56%
P-glycoprotein substrate	-	0.7385	73.85%
CYP3A4 substrate	+	0.5230	52.30%
CYP2C9 substrate	-	0.6882	68.82%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	+	0.5355	53.55%
CYP2C9 inhibition	-	0.6712	67.12%
CYP2C19 inhibition	+	0.5523	55.23%
CYP2D6 inhibition	-	0.8342	83.42%
CYP1A2 inhibition	-	0.6102	61.02%
CYP2C8 inhibition	+	0.4827	48.27%
CYP inhibitory promiscuity	+	0.5202	52.02%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5050	50.50%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.6436	64.36%
Skin irritation	-	0.7510	75.10%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7997	79.97%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.7198	71.98%
skin sensitisation	-	0.6070	60.70%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8098	80.98%
Acute Oral Toxicity (c)	III	0.5694	56.94%
Estrogen receptor binding	+	0.9285	92.85%
Androgen receptor binding	+	0.8720	87.20%
Thyroid receptor binding	+	0.6424	64.24%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	+	0.7806	78.06%
PPAR gamma	+	0.8189	81.89%
Honey bee toxicity	-	0.8110	81.10%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9705	97.05%

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	98.10%	91.11%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	97.31%	94.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.83%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.92%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.17%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.08%	94.00%
CHEMBL2581	P07339	Cathepsin D	86.97%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.56%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.37%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	82.99%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.99%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.46%	99.23%
CHEMBL1871	P10275	Androgen Receptor	81.87%	96.43%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.14%	99.17%

Plants that contains it

• Angelica dahurica
• Atalantia ceylanica
• Citrus maxima
• Citrus medica
• Ferula syreitschikowii
• Glehnia littoralis
• Hansenia forbesii
• Hansenia weberbaueriana
• Peucedanum ostruthium
• Prangos latiloba
• Prangos pabularia

Cross-Links

• PubChem: 33306
• NPASS: NPC295608
• LOTUS: LTS0030512
• wikiData: Q27104977