(3Z,3aS,7aS)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3a,7a-dihydro-2-benzofuran-1-one

Details

• Internal ID: 6bd1d392-e472-4f80-a3d7-7b1cfa40d463
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: (3Z,3aS,7aS)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3a,7a-dihydro-2-benzofuran-1-one
• SMILES (Canonical): C1=CC2C(C(=C1)O)C(=O)OC2=CC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C1=C[C@H]\2[C@@H](C(=C1)O)C(=O)O/C2=C\C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C15H12O5/c16-10-5-4-8(6-12(10)18)7-13-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,9,14,16-18H/b13-7-/t9-,14+/m1/s1
• InChI Key: GKIXLVBTAVQQEV-IAQOZEMSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	-	0.6779	67.79%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6061	60.61%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	+	0.9198	91.98%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8140	81.40%
P-glycoprotein inhibitior	-	0.8950	89.50%
P-glycoprotein substrate	-	0.9399	93.99%
CYP3A4 substrate	-	0.5205	52.05%
CYP2C9 substrate	-	0.6052	60.52%
CYP2D6 substrate	-	0.8525	85.25%
CYP3A4 inhibition	-	0.7302	73.02%
CYP2C9 inhibition	-	0.6421	64.21%
CYP2C19 inhibition	-	0.5942	59.42%
CYP2D6 inhibition	-	0.9152	91.52%
CYP1A2 inhibition	+	0.7419	74.19%
CYP2C8 inhibition	+	0.5529	55.29%
CYP inhibitory promiscuity	+	0.6349	63.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.3850	38.50%
Eye corrosion	-	0.9661	96.61%
Eye irritation	+	0.8733	87.33%
Skin irritation	+	0.6126	61.26%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8704	87.04%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.6109	61.09%
skin sensitisation	+	0.5343	53.43%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5666	56.66%
Acute Oral Toxicity (c)	IV	0.4245	42.45%
Estrogen receptor binding	+	0.8318	83.18%
Androgen receptor binding	+	0.5810	58.10%
Thyroid receptor binding	-	0.5495	54.95%
Glucocorticoid receptor binding	+	0.6912	69.12%
Aromatase binding	+	0.8218	82.18%
PPAR gamma	+	0.7626	76.26%
Honey bee toxicity	-	0.7416	74.16%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	99.51%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.06%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.06%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.80%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.16%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.45%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.94%	86.33%
CHEMBL3194	P02766	Transthyretin	87.01%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.64%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.29%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.87%	94.73%

Plants that contains it

• Hydrangea macrophylla

Cross-Links

• PubChem: 163186481
• LOTUS: LTS0192239
• wikiData: Q105010047