(2R,3'R,6'S)-3'-hydroxy-2',2',6'-trimethylspiro[3H-1-benzofuran-2,1'-cyclohexane]-5-carboxylic acid

Details

• Internal ID: 4441382d-b314-443b-a56e-e3eeb9969ddd
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (2R,3'R,6'S)-3'-hydroxy-2',2',6'-trimethylspiro[3H-1-benzofuran-2,1'-cyclohexane]-5-carboxylic acid
• SMILES (Canonical): CC1CCC(C(C12CC3=C(O2)C=CC(=C3)C(=O)O)(C)C)O
• SMILES (Isomeric): C[C@H]1CC[C@H](C([C@@]12CC3=C(O2)C=CC(=C3)C(=O)O)(C)C)O
• InChI: InChI=1S/C17H22O4/c1-10-4-7-14(18)16(2,3)17(10)9-12-8-11(15(19)20)5-6-13(12)21-17/h5-6,8,10,14,18H,4,7,9H2,1-3H3,(H,19,20)/t10-,14+,17+/m0/s1
• InChI Key: FKLYGOHUPOWMKU-NCAQKEMTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.6214	62.14%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8071	80.71%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9217	92.17%
OATP1B3 inhibitior	+	0.8623	86.23%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.8760	87.60%
P-glycoprotein inhibitior	-	0.9211	92.11%
P-glycoprotein substrate	-	0.7720	77.20%
CYP3A4 substrate	+	0.5419	54.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8060	80.60%
CYP3A4 inhibition	-	0.6220	62.20%
CYP2C9 inhibition	-	0.7929	79.29%
CYP2C19 inhibition	-	0.7977	79.77%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	+	0.6453	64.53%
CYP2C8 inhibition	-	0.6285	62.85%
CYP inhibitory promiscuity	-	0.9034	90.34%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5474	54.74%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8904	89.04%
Skin irritation	-	0.5853	58.53%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5980	59.80%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8665	86.65%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5879	58.79%
Acute Oral Toxicity (c)	I	0.3900	39.00%
Estrogen receptor binding	+	0.8922	89.22%
Androgen receptor binding	+	0.5430	54.30%
Thyroid receptor binding	+	0.5426	54.26%
Glucocorticoid receptor binding	+	0.6539	65.39%
Aromatase binding	+	0.7054	70.54%
PPAR gamma	+	0.8271	82.71%
Honey bee toxicity	-	0.9575	95.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7552	75.52%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.45%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.31%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.68%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.40%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.84%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.77%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.54%	95.56%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.33%	90.24%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	83.25%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.67%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.08%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.21%	99.23%

Plants that contains it

• Heliotropium filifolium

Cross-Links

• PubChem: 44416729
• LOTUS: LTS0010306
• wikiData: Q104996686