Tournefolic Acid B

Details

• Internal ID: 6a8257ea-128a-40c7-83f1-aa75b19d00d5
• Taxonomy: Organoheterocyclic compounds > Benzoxepines > Dibenzoxepines
• IUPAC Name: (E)-3-(2,3,10-trihydroxybenzo[b][1]benzoxepin-7-yl)prop-2-enoic acid
• SMILES (Canonical): C1=CC2=C(C=CC(=C2OC3=CC(=C(C=C31)O)O)O)C=CC(=O)O
• SMILES (Isomeric): C1=CC2=C(C=CC(=C2OC3=CC(=C(C=C31)O)O)O)/C=C/C(=O)O
• InChI: InChI=1S/C17H12O6/c18-12-5-2-9(3-6-16(21)22)11-4-1-10-7-13(19)14(20)8-15(10)23-17(11)12/h1-8,18-20H,(H,21,22)/b6-3+
• InChI Key: QOUSSKPKMYDXFC-ZZXKWVIFSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₆
• Molecular Weight: 312.27 g/mol
• Exact Mass: 312.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• CHEMBL464650
• (E)-3-(2,3,10-trihydroxybenzo[b][1]benzoxepin-7-yl)prop-2-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9692	96.92%
Caco-2	-	0.7994	79.94%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5324	53.24%
OATP2B1 inhibitior	-	0.5650	56.50%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6770	67.70%
P-glycoprotein inhibitior	-	0.8751	87.51%
P-glycoprotein substrate	-	0.9178	91.78%
CYP3A4 substrate	-	0.5373	53.73%
CYP2C9 substrate	-	0.5915	59.15%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.7608	76.08%
CYP2C9 inhibition	-	0.7594	75.94%
CYP2C19 inhibition	-	0.7626	76.26%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.6809	68.09%
CYP2C8 inhibition	+	0.5526	55.26%
CYP inhibitory promiscuity	-	0.7515	75.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5176	51.76%
Eye corrosion	-	0.9853	98.53%
Eye irritation	+	0.9740	97.40%
Skin irritation	+	0.6407	64.07%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7729	77.29%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.5372	53.72%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6362	63.62%
Acute Oral Toxicity (c)	II	0.4005	40.05%
Estrogen receptor binding	+	0.7999	79.99%
Androgen receptor binding	+	0.8536	85.36%
Thyroid receptor binding	+	0.6467	64.67%
Glucocorticoid receptor binding	+	0.8256	82.56%
Aromatase binding	+	0.5966	59.66%
PPAR gamma	+	0.7830	78.30%
Honey bee toxicity	-	0.9110	91.10%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	99.43%	91.11%
CHEMBL3194	P02766	Transthyretin	94.73%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	93.31%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.26%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.83%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.35%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.29%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.79%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.44%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.38%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.69%	99.17%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%

Plants that contains it

• Heliotropium sarmentosum

Cross-Links

• PubChem: 10018390
• LOTUS: LTS0013305
• wikiData: Q105225135