(1R,3S,6S,10S,11S,12R,13R)-12,13-dihydroxy-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradecan-8-one

Details

• Internal ID: b2f6a581-d972-4269-8070-97dd419ad489
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1R,3S,6S,10S,11S,12R,13R)-12,13-dihydroxy-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradecan-8-one
• SMILES (Canonical): CC12CCC3C(C4C1(O2)CC(C4(C)O)O)OC(=O)C3=C
• SMILES (Isomeric): C[C@]12CC[C@@H]3[C@@H]([C@@H]4[C@]1(O2)C[C@H]([C@]4(C)O)O)OC(=O)C3=C
• InChI: InChI=1S/C15H20O5/c1-7-8-4-5-13(2)15(20-13)6-9(16)14(3,18)11(15)10(8)19-12(7)17/h8-11,16,18H,1,4-6H2,2-3H3/t8-,9+,10-,11-,13-,14-,15+/m0/s1
• InChI Key: QURIQKIOFHIIMV-PETLWJBBSA-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): 79.30 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.54
• 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	+	0.9538	95.38%
Caco-2	-	0.5128	51.28%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6027	60.27%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8462	84.62%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.9726	97.26%
P-glycoprotein inhibitior	-	0.9230	92.30%
P-glycoprotein substrate	-	0.8326	83.26%
CYP3A4 substrate	+	0.6377	63.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8469	84.69%
CYP3A4 inhibition	-	0.7013	70.13%
CYP2C9 inhibition	-	0.7416	74.16%
CYP2C19 inhibition	-	0.7632	76.32%
CYP2D6 inhibition	-	0.9303	93.03%
CYP1A2 inhibition	+	0.5884	58.84%
CYP2C8 inhibition	-	0.6896	68.96%
CYP inhibitory promiscuity	-	0.9720	97.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5095	50.95%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.5173	51.73%
Skin corrosion	-	0.8961	89.61%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6475	64.75%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.7949	79.49%
skin sensitisation	-	0.7969	79.69%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.8001	80.01%
Acute Oral Toxicity (c)	III	0.3365	33.65%
Estrogen receptor binding	+	0.7712	77.12%
Androgen receptor binding	+	0.6947	69.47%
Thyroid receptor binding	+	0.5798	57.98%
Glucocorticoid receptor binding	+	0.7158	71.58%
Aromatase binding	-	0.5117	51.17%
PPAR gamma	-	0.5595	55.95%
Honey bee toxicity	-	0.7662	76.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9811	98.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	93.09%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.59%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.37%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.11%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.84%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.13%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.08%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.35%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.97%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.12%	97.14%

Plants that contains it

• Artemisia filatovae

Cross-Links

• PubChem: 162937860
• LOTUS: LTS0270089
• wikiData: Q105228380