Rufuslactone

Details

• Internal ID: 3938cb80-9922-4898-8a2b-043fdcbb0996
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1S,8S,9S,13R)-8,11,11-trimethyl-4,14-dioxatetracyclo[6.5.1.02,6.09,13]tetradec-2(6)-en-5-one
• SMILES (Canonical): CC1(CC2C(C1)C3(CC4=C(C2O3)COC4=O)C)C
• SMILES (Isomeric): C[C@@]12CC3=C(COC3=O)[C@@H](O1)[C@H]4[C@@H]2CC(C4)(C)C
• InChI: InChI=1S/C15H20O3/c1-14(2)4-9-11(6-14)15(3)5-8-10(12(9)18-15)7-17-13(8)16/h9,11-12H,4-7H2,1-3H3/t9-,11+,12+,15+/m1/s1
• InChI Key: IEGUGMUAHGJATF-ZFVXVEAMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (1S,8S,9S,13R)-8,11,11-trimethyl-4,14-dioxatetracyclo[6.5.1.02,6.09,13]tetradec-2(6)-en-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.7085	70.85%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7221	72.21%
OATP2B1 inhibitior	-	0.8500	85.00%
OATP1B1 inhibitior	+	0.9362	93.62%
OATP1B3 inhibitior	+	0.9629	96.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7677	76.77%
P-glycoprotein inhibitior	-	0.7824	78.24%
P-glycoprotein substrate	-	0.8516	85.16%
CYP3A4 substrate	+	0.5507	55.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8820	88.20%
CYP3A4 inhibition	-	0.9291	92.91%
CYP2C9 inhibition	-	0.8277	82.77%
CYP2C19 inhibition	-	0.8100	81.00%
CYP2D6 inhibition	-	0.9173	91.73%
CYP1A2 inhibition	-	0.6796	67.96%
CYP2C8 inhibition	-	0.9124	91.24%
CYP inhibitory promiscuity	-	0.8995	89.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9720	97.20%
Eye irritation	-	0.8188	81.88%
Skin irritation	-	0.6796	67.96%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4140	41.40%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6282	62.82%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.9142	91.42%
Acute Oral Toxicity (c)	III	0.5088	50.88%
Estrogen receptor binding	+	0.5828	58.28%
Androgen receptor binding	+	0.6200	62.00%
Thyroid receptor binding	-	0.5325	53.25%
Glucocorticoid receptor binding	+	0.7382	73.82%
Aromatase binding	-	0.7968	79.68%
PPAR gamma	-	0.6111	61.11%
Honey bee toxicity	-	0.7433	74.33%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9765	97.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.48%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.69%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.82%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.18%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.22%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.65%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.21%	94.45%
CHEMBL2039	P27338	Monoamine oxidase B	83.17%	92.51%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.95%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.70%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	81.37%	97.79%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.56%	96.77%

Plants that contains it

• Stephania delavayi

Cross-Links

• PubChem: 15330797
• NPASS: NPC299344