Prenyletin

Details

• Internal ID: 5b1c901d-8f21-4d57-8781-054940828fe5
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 6-hydroxy-7-(3-methylbut-2-enoxy)chromen-2-one
• SMILES (Canonical): CC(=CCOC1=C(C=C2C=CC(=O)OC2=C1)O)C
• SMILES (Isomeric): CC(=CCOC1=C(C=C2C=CC(=O)OC2=C1)O)C
• InChI: InChI=1S/C14H14O4/c1-9(2)5-6-17-13-8-12-10(7-11(13)15)3-4-14(16)18-12/h3-5,7-8,15H,6H2,1-2H3
• InChI Key: AWEFUQDNSBBNCR-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 15870-91-4
• 6-hydroxy-7-(3-methylbut-2-enoxy)chromen-2-one
• 6-Hydroxy-7-(isopentenyloxy)-2H-1-benzopyran-2-one
• KBio2_003658
• Spectrum_000610
• SpecPlus_000123
• Spectrum2_000250
• Spectrum3_000034
• Spectrum4_001315
• Spectrum5_000129
• BSPBio_001727
• KBioGR_001749
• KBioSS_001090
• SPECTRUM100101
• DivK1c_006219
• SPBio_000040
• CHEMBL607536
• SCHEMBL12062090
• KBio1_001163
• KBio2_001090
• KBio2_006226
• KBio3_000867
• DTXSID101347414
• CCG-39811
• SDCCGMLS-0066355.P001
• NCGC00095380-01
• NCGC00095380-02
• SR-05000002493
• SR-05000002493-1
• BRD-K81750404-001-02-5
• BRD-K81750404-001-03-3
• 6-Hydroxy-7-[(3-methyl-2-buten-1-yl)oxy]-2H-chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	+	0.9336	93.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7924	79.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4751	47.51%
P-glycoprotein inhibitior	-	0.8080	80.80%
P-glycoprotein substrate	-	0.8784	87.84%
CYP3A4 substrate	-	0.5892	58.92%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8336	83.36%
CYP3A4 inhibition	-	0.8028	80.28%
CYP2C9 inhibition	+	0.8747	87.47%
CYP2C19 inhibition	+	0.9169	91.69%
CYP2D6 inhibition	+	0.5495	54.95%
CYP1A2 inhibition	+	0.9117	91.17%
CYP2C8 inhibition	-	0.7561	75.61%
CYP inhibitory promiscuity	+	0.8495	84.95%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7432	74.32%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.7504	75.04%
Skin irritation	-	0.7332	73.32%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5340	53.40%
Micronuclear	-	0.5326	53.26%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7621	76.21%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5234	52.34%
Acute Oral Toxicity (c)	III	0.5504	55.04%
Estrogen receptor binding	+	0.8245	82.45%
Androgen receptor binding	+	0.5452	54.52%
Thyroid receptor binding	-	0.5797	57.97%
Glucocorticoid receptor binding	-	0.4879	48.79%
Aromatase binding	+	0.8597	85.97%
PPAR gamma	+	0.7731	77.31%
Honey bee toxicity	-	0.9211	92.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	25118.9 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	2511.9 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	97.73%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.01%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.71%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.09%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.10%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.74%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	85.96%	91.49%
CHEMBL4208	P20618	Proteasome component C5	84.61%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.71%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.94%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.65%	96.95%
CHEMBL1937	Q92769	Histone deacetylase 2	82.16%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.86%	89.00%

Plants that contains it

• Aldama gardneri
• Aldama robusta
• Angelica gigas
• Angiopteris evecta
• Bupleurum fruticosum
• Byrsonima microphylla
• Cassipourea guianensis
• Crotalaria madurensis
• Flourensia thurifera
• Gymnosporia senegalensis
• Haplopappus multifolius
• Ifloga spicata
• Lomatia silaifolia
• Nidorella hottentotica
• Pterocaulon polystachyum

Cross-Links

• PubChem: 3873459
• NPASS: NPC13067
• ChEMBL: CHEMBL607536
• LOTUS: LTS0029951
• wikiData: Q104397279