(3E,5S)-5-(3,4-dihydroxyphenyl)-3-[(3,4-dihydroxyphenyl)methylidene]oxolan-2-one

Details

• Internal ID: 06b9d8ec-3626-43ec-a4fa-3fe5b7c74017
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: (3E,5S)-5-(3,4-dihydroxyphenyl)-3-[(3,4-dihydroxyphenyl)methylidene]oxolan-2-one
• SMILES (Canonical): C1C(OC(=O)C1=CC2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C\1[C@H](OC(=O)/C1=C/C2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C17H14O6/c18-12-3-1-9(6-14(12)20)5-11-8-16(23-17(11)22)10-2-4-13(19)15(21)7-10/h1-7,16,18-21H,8H2/b11-5+/t16-/m0/s1
• InChI Key: UBOOMSUOPIZYEU-WQRDJFRPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.07903816 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	-	0.7458	74.58%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7834	78.34%
OATP2B1 inhibitior	-	0.5762	57.62%
OATP1B1 inhibitior	+	0.9429	94.29%
OATP1B3 inhibitior	+	0.8892	88.92%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5819	58.19%
P-glycoprotein inhibitior	-	0.9168	91.68%
P-glycoprotein substrate	-	0.9784	97.84%
CYP3A4 substrate	-	0.5666	56.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8113	81.13%
CYP3A4 inhibition	-	0.7844	78.44%
CYP2C9 inhibition	+	0.6253	62.53%
CYP2C19 inhibition	+	0.5545	55.45%
CYP2D6 inhibition	-	0.8893	88.93%
CYP1A2 inhibition	+	0.5384	53.84%
CYP2C8 inhibition	-	0.8023	80.23%
CYP inhibitory promiscuity	+	0.7882	78.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4337	43.37%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.8069	80.69%
Skin irritation	-	0.6595	65.95%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	-	0.5598	55.98%
skin sensitisation	-	0.5876	58.76%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5633	56.33%
Acute Oral Toxicity (c)	III	0.4422	44.22%
Estrogen receptor binding	+	0.8234	82.34%
Androgen receptor binding	+	0.7206	72.06%
Thyroid receptor binding	+	0.7280	72.80%
Glucocorticoid receptor binding	+	0.6694	66.94%
Aromatase binding	-	0.4863	48.63%
PPAR gamma	+	0.7318	73.18%
Honey bee toxicity	-	0.8693	86.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9924	99.24%

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	99.82%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.04%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.07%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.90%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.16%	96.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.00%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.96%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.54%	93.40%
CHEMBL2581	P07339	Cathepsin D	83.38%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	82.06%	94.73%
CHEMBL3194	P02766	Transthyretin	81.86%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.45%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.07%	94.45%

Plants that contains it

• Scorzonera psychrophila

Cross-Links

• PubChem: 163194497
• LOTUS: LTS0068326
• wikiData: Q105269550