(1R,8R,9R,10S,11S,12S)-9,10-dihydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.04,12.08,12]tetradec-3-en-5-one

Details

• Internal ID: 5a447511-8b39-4e69-a64d-6eaf3cb40323
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1R,8R,9R,10S,11S,12S)-9,10-dihydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.04,12.08,12]tetradec-3-en-5-one
• SMILES (Canonical): CC1(C2CC=C3C(=O)OCC4C3(C2)C1C(C4O)O)C
• SMILES (Isomeric): CC1([C@@H]2CC=C3C(=O)OC[C@H]4[C@]3(C2)[C@H]1[C@@H]([C@@H]4O)O)C
• InChI: InChI=1S/C15H20O4/c1-14(2)7-3-4-8-13(18)19-6-9-10(16)11(17)12(14)15(8,9)5-7/h4,7,9-12,16-17H,3,5-6H2,1-2H3/t7-,9-,10-,11-,12+,15-/m1/s1
• InChI Key: RPENBJGKZCCIDL-PWEOXZDBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 4
• 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	+	0.9624	96.24%
Caco-2	+	0.6785	67.85%
Blood Brain Barrier	-	0.6964	69.64%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8333	83.33%
OATP2B1 inhibitior	-	0.8515	85.15%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9012	90.12%
P-glycoprotein inhibitior	-	0.9295	92.95%
P-glycoprotein substrate	-	0.7643	76.43%
CYP3A4 substrate	+	0.5596	55.96%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8635	86.35%
CYP3A4 inhibition	-	0.9118	91.18%
CYP2C9 inhibition	-	0.7597	75.97%
CYP2C19 inhibition	-	0.7415	74.15%
CYP2D6 inhibition	-	0.8815	88.15%
CYP1A2 inhibition	-	0.6461	64.61%
CYP2C8 inhibition	-	0.8427	84.27%
CYP inhibitory promiscuity	-	0.8859	88.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6477	64.77%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.8506	85.06%
Skin irritation	-	0.6236	62.36%
Skin corrosion	-	0.9341	93.41%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7755	77.55%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6312	63.12%
Acute Oral Toxicity (c)	III	0.3986	39.86%
Estrogen receptor binding	-	0.5678	56.78%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5525	55.25%
Glucocorticoid receptor binding	-	0.5332	53.32%
Aromatase binding	-	0.6308	63.08%
PPAR gamma	-	0.7731	77.31%
Honey bee toxicity	-	0.8314	83.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	96.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.06%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.30%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.66%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.95%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.15%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.59%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.13%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.27%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.14%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.01%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.12%	94.45%

Plants that contains it

• Jungia stuebelii

Cross-Links

• PubChem: 163105851
• LOTUS: LTS0042197
• wikiData: Q105242640