Obovatal

Details

• Internal ID: c2d04afc-4895-4dcc-8722-52e7b996f5cb
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Diphenylethers
• IUPAC Name: (E)-3-[3,4-dihydroxy-5-(4-prop-2-enylphenoxy)phenyl]prop-2-enal
• SMILES (Canonical): C=CCC1=CC=C(C=C1)OC2=CC(=CC(=C2O)O)C=CC=O
• SMILES (Isomeric): C=CCC1=CC=C(C=C1)OC2=CC(=CC(=C2O)O)/C=C/C=O
• InChI: InChI=1S/C18H16O4/c1-2-4-13-6-8-15(9-7-13)22-17-12-14(5-3-10-19)11-16(20)18(17)21/h2-3,5-12,20-21H,1,4H2/b5-3+
• InChI Key: KGHJODCHEIEYBP-HWKANZROSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.30 g/mol
• Exact Mass: 296.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 83864-77-1
• 3,4-Dihydroxy-5-(4-allylphenoxy)cinnamic aldehyde
• (E)-3-[3,4-dihydroxy-5-(4-prop-2-enylphenoxy)phenyl]prop-2-enal
• (E)-3-(3,4-dihydroxy-5-(4-prop-2-enylphenoxy)phenyl)prop-2-enal
• RefChem:167394
• CHEMBL242530
• SCHEMBL3383286
• BDBM50210455
• 3-(3-(4-allylphenoxy)-4,5-dihydroxyphenyl)acrylaldehyde
• (E)-3-(3-(4-Allylphenoxy)-4,5-dihydroxyphenyl)acrylaldehyde
• 2-Propenal, 3-(3,4-dihydroxy-5-(4-(2-propenyl)phenoxy)phenyl)-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9721	97.21%
Caco-2	-	0.8134	81.34%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7727	77.27%
OATP2B1 inhibitior	-	0.7207	72.07%
OATP1B1 inhibitior	+	0.8730	87.30%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5640	56.40%
P-glycoprotein inhibitior	-	0.7862	78.62%
P-glycoprotein substrate	-	0.9240	92.40%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.7959	79.59%
CYP3A4 inhibition	+	0.5534	55.34%
CYP2C9 inhibition	-	0.5398	53.98%
CYP2C19 inhibition	-	0.5496	54.96%
CYP2D6 inhibition	-	0.8811	88.11%
CYP1A2 inhibition	+	0.8390	83.90%
CYP2C8 inhibition	+	0.7571	75.71%
CYP inhibitory promiscuity	+	0.6619	66.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7666	76.66%
Carcinogenicity (trinary)	Non-required	0.5952	59.52%
Eye corrosion	-	0.9687	96.87%
Eye irritation	+	0.9209	92.09%
Skin irritation	-	0.5875	58.75%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4549	45.49%
Micronuclear	+	0.7359	73.59%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	+	0.7516	75.16%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7144	71.44%
Acute Oral Toxicity (c)	III	0.8650	86.50%
Estrogen receptor binding	+	0.8514	85.14%
Androgen receptor binding	+	0.6989	69.89%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	+	0.6873	68.73%
Aromatase binding	+	0.8862	88.62%
PPAR gamma	+	0.8185	81.85%
Honey bee toxicity	-	0.7563	75.63%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9965	99.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL333	P08253	Matrix metalloproteinase-2	800 nM	IC50	PMID: 17428670

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.51%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	95.99%	91.49%
CHEMBL3194	P02766	Transthyretin	95.63%	90.71%
CHEMBL4208	P20618	Proteasome component C5	91.58%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.26%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.85%	90.24%
CHEMBL3401	O75469	Pregnane X receptor	89.51%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.37%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.30%	80.78%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.17%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.98%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.23%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.08%	95.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.21%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.51%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.77%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.32%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.32%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.59%	91.71%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.07%	92.32%
CHEMBL2581	P07339	Cathepsin D	80.92%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.57%	96.12%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.13%	93.40%

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
• Suaeda maritima
• Torminalis glaberrima
• Triunia erythrocarpa

Cross-Links

• PubChem: 6439677
• NPASS: NPC36490
• ChEMBL: CHEMBL242530
• LOTUS: LTS0078198
• wikiData: Q105140781