(3R,3aR,6R,6aS,10aS)-3-hydroxy-3,6-dimethyl-2,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-9-carboxylic acid

Details

• Internal ID: 36ff0768-42e4-4914-9052-25d3d6343493
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (3R,3aR,6R,6aS,10aS)-3-hydroxy-3,6-dimethyl-2,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-9-carboxylic acid
• SMILES (Canonical): CC1CCC2C(COC23C1CCC(=C3)C(=O)O)(C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@H]2[C@@](CO[C@]23[C@H]1CCC(=C3)C(=O)O)(C)O
• InChI: InChI=1S/C15H22O4/c1-9-3-6-12-14(2,18)8-19-15(12)7-10(13(16)17)4-5-11(9)15/h7,9,11-12,18H,3-6,8H2,1-2H3,(H,16,17)/t9-,11+,12-,14+,15-/m1/s1
• InChI Key: CUJOWLDRULOIOA-MYDLQGKQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (3R,3aR,6R,6aS,10aS)-3-hydroxy-3,6-dimethyl-2,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzouran-9-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.8605	86.05%
Blood Brain Barrier	+	0.5034	50.34%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7925	79.25%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9643	96.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5493	54.93%
BSEP inhibitior	-	0.9211	92.11%
P-glycoprotein inhibitior	-	0.9395	93.95%
P-glycoprotein substrate	-	0.8510	85.10%
CYP3A4 substrate	+	0.5403	54.03%
CYP2C9 substrate	-	0.6056	60.56%
CYP2D6 substrate	-	0.8888	88.88%
CYP3A4 inhibition	-	0.8136	81.36%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.8990	89.90%
CYP2D6 inhibition	-	0.9146	91.46%
CYP1A2 inhibition	-	0.8088	80.88%
CYP2C8 inhibition	+	0.4527	45.27%
CYP inhibitory promiscuity	-	0.9283	92.83%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5030	50.30%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.7991	79.91%
Skin irritation	+	0.5053	50.53%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7114	71.14%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5768	57.68%
Acute Oral Toxicity (c)	III	0.3969	39.69%
Estrogen receptor binding	-	0.4841	48.41%
Androgen receptor binding	+	0.6726	67.26%
Thyroid receptor binding	+	0.6953	69.53%
Glucocorticoid receptor binding	+	0.5688	56.88%
Aromatase binding	-	0.6608	66.08%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9302	93.02%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9746	97.46%

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	95.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.61%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.93%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.46%	93.56%
CHEMBL5028	O14672	ADAM10	82.92%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.29%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	82.15%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.65%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.42%	93.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 145720930
• LOTUS: LTS0007850
• wikiData: Q104970313