(1R,2R,4S,5R,6S,13S)-4,5-dihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione

Details

• Internal ID: b1947db5-5166-4d0d-aa3a-a9a00a57c7a0
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: (1R,2R,4S,5R,6S,13S)-4,5-dihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione
• SMILES (Canonical): CC1CC(C2(C13CC(=O)C(C2(COC(=O)C3)C)C)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@]2([C@@]13CC(=O)[C@H]([C@]2(COC(=O)C3)C)C)O)O
• InChI: InChI=1S/C15H22O5/c1-8-4-11(17)15(19)13(3)7-20-12(18)6-14(8,15)5-10(16)9(13)2/h8-9,11,17,19H,4-7H2,1-3H3/t8-,9-,11+,13-,14-,15+/m1/s1
• InChI Key: PZVGVKOLTVKLNQ-SZLRVMPYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9194	91.94%
Caco-2	+	0.6413	64.13%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6790	67.90%
OATP2B1 inhibitior	-	0.8471	84.71%
OATP1B1 inhibitior	+	0.9359	93.59%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8702	87.02%
P-glycoprotein inhibitior	-	0.9304	93.04%
P-glycoprotein substrate	-	0.7464	74.64%
CYP3A4 substrate	+	0.5784	57.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8426	84.26%
CYP3A4 inhibition	-	0.7921	79.21%
CYP2C9 inhibition	-	0.9046	90.46%
CYP2C19 inhibition	-	0.8925	89.25%
CYP2D6 inhibition	-	0.9725	97.25%
CYP1A2 inhibition	-	0.7655	76.55%
CYP2C8 inhibition	-	0.9153	91.53%
CYP inhibitory promiscuity	-	0.9944	99.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6415	64.15%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8684	86.84%
Skin irritation	-	0.6204	62.04%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5797	57.97%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5667	56.67%
skin sensitisation	-	0.8958	89.58%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6874	68.74%
Acute Oral Toxicity (c)	III	0.3520	35.20%
Estrogen receptor binding	-	0.5646	56.46%
Androgen receptor binding	+	0.6560	65.60%
Thyroid receptor binding	-	0.6143	61.43%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5555	55.55%
PPAR gamma	-	0.7838	78.38%
Honey bee toxicity	-	0.8486	84.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9569	95.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.43%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.73%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.36%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.94%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.13%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.76%	85.14%
CHEMBL2581	P07339	Cathepsin D	83.70%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.82%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.32%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.66%	96.95%

Plants that contains it

• Illicium dunnianum

Cross-Links

• PubChem: 14168250
• LOTUS: LTS0180308
• wikiData: Q105217159