2-[(2'S,4R,4aR,8R,8aS)-4-hydroxy-2',4,7,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid

Details

• Internal ID: 057b813c-f0e8-4d8a-b121-0a06dbf2b904
• Taxonomy: Organoheterocyclic compounds > Tetrahydrofurans
• IUPAC Name: 2-[(2'S,4R,4aR,8R,8aS)-4-hydroxy-2',4,7,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CCC2C(C13CCC(O3)(C)CC(=O)O)(CCCC2(C)O)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CC(=O)O)(CCC[C@@]2(C)O)C
• InChI: InChI=1S/C19H30O4/c1-13-6-7-14-17(3,8-5-9-18(14,4)22)19(13)11-10-16(2,23-19)12-15(20)21/h6,14,22H,5,7-12H2,1-4H3,(H,20,21)/t14-,16+,17+,18-,19-/m1/s1
• InChI Key: UNXOXLATZGHFCT-QFACEVIFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.6789	67.89%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6610	66.10%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8507	85.07%
OATP1B3 inhibitior	+	0.9152	91.52%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5502	55.02%
P-glycoprotein inhibitior	-	0.8704	87.04%
P-glycoprotein substrate	-	0.8989	89.89%
CYP3A4 substrate	+	0.5513	55.13%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8615	86.15%
CYP3A4 inhibition	-	0.5671	56.71%
CYP2C9 inhibition	-	0.8855	88.55%
CYP2C19 inhibition	-	0.8405	84.05%
CYP2D6 inhibition	-	0.9484	94.84%
CYP1A2 inhibition	-	0.7886	78.86%
CYP2C8 inhibition	-	0.6642	66.42%
CYP inhibitory promiscuity	-	0.8583	85.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5309	53.09%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8148	81.48%
Skin irritation	+	0.6234	62.34%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.6791	67.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4780	47.80%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7877	78.77%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8352	83.52%
Acute Oral Toxicity (c)	I	0.4890	48.90%
Estrogen receptor binding	+	0.7422	74.22%
Androgen receptor binding	+	0.5960	59.60%
Thyroid receptor binding	+	0.6782	67.82%
Glucocorticoid receptor binding	-	0.4799	47.99%
Aromatase binding	+	0.7845	78.45%
PPAR gamma	+	0.5170	51.70%
Honey bee toxicity	-	0.9705	97.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9840	98.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	92.35%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.43%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.62%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.35%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.60%	86.33%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 163106191
• LOTUS: LTS0031727
• wikiData: Q105276200