Coumanolignan

Details

• Internal ID: 98207712-87be-4993-88f9-c75a2f1187e8
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 8-(2-hydroxy-5-prop-2-enylphenyl)-6-prop-2-enylchromen-2-one
• SMILES (Canonical): C=CCC1=CC(=C(C=C1)O)C2=C3C(=CC(=C2)CC=C)C=CC(=O)O3
• SMILES (Isomeric): C=CCC1=CC(=C(C=C1)O)C2=C3C(=CC(=C2)CC=C)C=CC(=O)O3
• InChI: InChI=1S/C21H18O3/c1-3-5-14-7-9-19(22)17(12-14)18-13-15(6-4-2)11-16-8-10-20(23)24-21(16)18/h3-4,7-13,22H,1-2,5-6H2
• InChI Key: ZVUXKRKDLKXWJI-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• SCHEMBL18838052
• 8-(2-hydroxy-5-prop-2-enylphenyl)-6-prop-2-enylchromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	-	0.7379	73.79%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6509	65.09%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.9142	91.42%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7316	73.16%
P-glycoprotein inhibitior	-	0.5255	52.55%
P-glycoprotein substrate	-	0.9096	90.96%
CYP3A4 substrate	-	0.5935	59.35%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8039	80.39%
CYP3A4 inhibition	-	0.6845	68.45%
CYP2C9 inhibition	+	0.8458	84.58%
CYP2C19 inhibition	-	0.5368	53.68%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.8649	86.49%
CYP2C8 inhibition	+	0.5372	53.72%
CYP inhibitory promiscuity	+	0.5211	52.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.5735	57.35%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.6655	66.55%
Skin irritation	+	0.5725	57.25%
Skin corrosion	-	0.9717	97.17%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5410	54.10%
Micronuclear	+	0.7659	76.59%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.6366	63.66%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7639	76.39%
Acute Oral Toxicity (c)	II	0.5873	58.73%
Estrogen receptor binding	+	0.7184	71.84%
Androgen receptor binding	+	0.8481	84.81%
Thyroid receptor binding	+	0.6326	63.26%
Glucocorticoid receptor binding	+	0.8456	84.56%
Aromatase binding	+	0.8102	81.02%
PPAR gamma	+	0.9520	95.20%
Honey bee toxicity	-	0.8214	82.14%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9926	99.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	95.32%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.67%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.62%	96.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.60%	90.24%
CHEMBL3401	O75469	Pregnane X receptor	86.49%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.20%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.41%	94.00%
CHEMBL4530	P00488	Coagulation factor XIII	83.64%	96.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.53%	80.78%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.37%	85.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.33%	90.71%
CHEMBL3194	P02766	Transthyretin	80.97%	90.71%

Plants that contains it

• Alpinia flabellata
• Angelica japonica
• Baccharis truncata
• Benincasa hispida
• Centaurea benedicta
• Chloranthus fortunei
• Chuquiraga erinacea
• Cuphea hyssopifolia
• Cylindrolobus mucronatus
• Euphorbia palustris
• Euphorbia pithyusa
• Farfugium japonicum
• Fouquieria diguetii
• Fritillaria monantha
• Holarrhena floribunda
• Lathyrus latifolius
• Magnolia obovata
• Ononis viscosa
• Paragynoxys meridana
• Pedicularis rex
• Pinus edulis
• Posidonia oceanica
• Pterocarpus erinaceus
• Pyrus bourgaeana
• Salvia broussonetii
• Sandoricum koetjape
• Sedum sarmentosum
• Sorbus torminalis
• Suaeda maritima
• Triunia erythrocarpa

Cross-Links

• PubChem: 24796112
• NPASS: NPC105004
• LOTUS: LTS0118224
• wikiData: Q105384678