(3R,5R,8S,10S,12S)-12-hydroxy-5,10,15-trimethyl-4,9,13-trioxatetracyclo[10.3.0.03,5.08,10]pentadec-1(15)-en-14-one

Details

• Internal ID: 5ef12e0c-5be4-43e5-a791-eeb76b23cbb8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,5R,8S,10S,12S)-12-hydroxy-5,10,15-trimethyl-4,9,13-trioxatetracyclo[10.3.0.03,5.08,10]pentadec-1(15)-en-14-one
• SMILES (Canonical): CC1=C2CC3C(O3)(CCC4C(O4)(CC2(OC1=O)O)C)C
• SMILES (Isomeric): CC1=C2C[C@@H]3[C@](O3)(CC[C@H]4[C@@](O4)(C[C@@]2(OC1=O)O)C)C
• InChI: InChI=1S/C15H20O5/c1-8-9-6-11-13(2,19-11)5-4-10-14(3,18-10)7-15(9,17)20-12(8)16/h10-11,17H,4-7H2,1-3H3/t10-,11+,13+,14-,15-/m0/s1
• InChI Key: HHGREWJPFBZWTH-LWOQNUMLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 71.60 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	+	0.8245	82.45%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6667	66.67%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9411	94.11%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5608	56.08%
P-glycoprotein inhibitior	-	0.8505	85.05%
P-glycoprotein substrate	-	0.8781	87.81%
CYP3A4 substrate	+	0.6083	60.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8671	86.71%
CYP3A4 inhibition	-	0.7667	76.67%
CYP2C9 inhibition	-	0.8190	81.90%
CYP2C19 inhibition	-	0.9064	90.64%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	+	0.5379	53.79%
CYP2C8 inhibition	-	0.8822	88.22%
CYP inhibitory promiscuity	-	0.9734	97.34%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4712	47.12%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.7976	79.76%
Skin irritation	+	0.5477	54.77%
Skin corrosion	-	0.8976	89.76%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5099	50.99%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5951	59.51%
skin sensitisation	-	0.7729	77.29%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6973	69.73%
Acute Oral Toxicity (c)	III	0.3957	39.57%
Estrogen receptor binding	+	0.6804	68.04%
Androgen receptor binding	+	0.6117	61.17%
Thyroid receptor binding	+	0.7506	75.06%
Glucocorticoid receptor binding	+	0.7374	73.74%
Aromatase binding	+	0.5655	56.55%
PPAR gamma	+	0.6891	68.91%
Honey bee toxicity	-	0.9145	91.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9598	95.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.19%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.65%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.78%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.48%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.03%	82.69%
CHEMBL1902	P62942	FK506-binding protein 1A	81.40%	97.05%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.25%	93.00%

Plants that contains it

• Smyrnium olusatrum

Cross-Links

• PubChem: 162887375
• LOTUS: LTS0019908
• wikiData: Q105028279