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

Details

• Internal ID: 27f9c7bc-537a-4206-b8d0-7f55a3c189a6
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: (1R,2S,5R,6R,13R)-2,5,13-trihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione
• SMILES (Canonical): CC1(CCC2(C13CC(=O)C(C2(COC(=O)C3)C)(C)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@]2([C@@]13CC(=O)[C@]([C@@]2(COC(=O)C3)C)(C)O)O)O
• InChI: InChI=1S/C15H22O6/c1-11-8-21-10(17)7-14(6-9(16)13(11,3)19)12(2,18)4-5-15(11,14)20/h18-20H,4-8H2,1-3H3/t11-,12-,13-,14+,15-/m0/s1
• InChI Key: FZTKPYZYPMEOEN-LXFSFDBISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.33 g/mol
• Exact Mass: 298.14163842 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8825	88.25%
Caco-2	+	0.6964	69.64%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6731	67.31%
OATP2B1 inhibitior	-	0.8484	84.84%
OATP1B1 inhibitior	+	0.9279	92.79%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7759	77.59%
BSEP inhibitior	-	0.7892	78.92%
P-glycoprotein inhibitior	-	0.9292	92.92%
P-glycoprotein substrate	-	0.8421	84.21%
CYP3A4 substrate	+	0.5678	56.78%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.8411	84.11%
CYP3A4 inhibition	-	0.8471	84.71%
CYP2C9 inhibition	-	0.8412	84.12%
CYP2C19 inhibition	-	0.8905	89.05%
CYP2D6 inhibition	-	0.9710	97.10%
CYP1A2 inhibition	-	0.7698	76.98%
CYP2C8 inhibition	-	0.9495	94.95%
CYP inhibitory promiscuity	-	0.9894	98.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6872	68.72%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.5409	54.09%
Skin irritation	-	0.5494	54.94%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5455	54.55%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	-	0.9194	91.94%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7633	76.33%
Acute Oral Toxicity (c)	III	0.3901	39.01%
Estrogen receptor binding	-	0.6131	61.31%
Androgen receptor binding	+	0.6403	64.03%
Thyroid receptor binding	-	0.6652	66.52%
Glucocorticoid receptor binding	-	0.6842	68.42%
Aromatase binding	+	0.5405	54.05%
PPAR gamma	-	0.8372	83.72%
Honey bee toxicity	-	0.8992	89.92%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9152	91.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	89.74%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.18%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.39%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.87%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.16%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.59%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	82.59%	83.82%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.46%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.26%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	80.55%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.54%	100.00%

Plants that contains it

• Illicium parvifolium subsp. oligandrum

Cross-Links

• PubChem: 16053028
• LOTUS: LTS0056188
• wikiData: Q105005175