(1R,2R,5S,7R)-9-Hydroxy-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undec-8-ene-10,11-dione

Details

• Internal ID: 772a4fcf-2679-4264-85f7-e08d3c16aabd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Cedrane and isocedrane sesquiterpenoids
• IUPAC Name: (1R,2R,5S,7R)-9-hydroxy-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undec-8-ene-10,11-dione
• SMILES (Canonical): CC1CCC2C13C(=O)C(C2(C)C)C(=C(C3=O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@H]2[C@@]13C(=O)[C@H](C2(C)C)C(=C(C3=O)O)C
• InChI: InChI=1S/C15H20O3/c1-7-5-6-9-14(3,4)10-8(2)11(16)13(18)15(7,9)12(10)17/h7,9-10,16H,5-6H2,1-4H3/t7-,9+,10-,15-/m1/s1
• InChI Key: JSYQPAIDLVPBDA-RAIZXLCNSA-N
• Popularity: 5 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): 54.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (1R,2R,5S,7R)-9-Hydroxy-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undec-8-ene-10,11-dione
• beta-Pipitzol
• 4H-3a,7-Methanoazulene-4,9-dione, 1,2,3,7,8,8a-hexahydro-5-hydroxy-3,6,8,8-tetramethyl-, (3R-(3alpha,3aalpha,7alpha,8abeta))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.5062	50.62%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6529	65.29%
OATP2B1 inhibitior	-	0.8491	84.91%
OATP1B1 inhibitior	+	0.9135	91.35%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9674	96.74%
P-glycoprotein inhibitior	-	0.8884	88.84%
P-glycoprotein substrate	-	0.8969	89.69%
CYP3A4 substrate	+	0.5433	54.33%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.8995	89.95%
CYP2C9 inhibition	-	0.7297	72.97%
CYP2C19 inhibition	-	0.8588	85.88%
CYP2D6 inhibition	-	0.8984	89.84%
CYP1A2 inhibition	-	0.6107	61.07%
CYP2C8 inhibition	-	0.9262	92.62%
CYP inhibitory promiscuity	-	0.8893	88.93%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5082	50.82%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.7001	70.01%
Skin irritation	+	0.6602	66.02%
Skin corrosion	-	0.8642	86.42%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6500	65.00%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5385	53.85%
skin sensitisation	+	0.6246	62.46%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6126	61.26%
Acute Oral Toxicity (c)	III	0.5869	58.69%
Estrogen receptor binding	+	0.6654	66.54%
Androgen receptor binding	-	0.5292	52.92%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5593	55.93%
Aromatase binding	-	0.7395	73.95%
PPAR gamma	-	0.5793	57.93%
Honey bee toxicity	-	0.9035	90.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9702	97.02%

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	89.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.58%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.87%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.94%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	86.78%	94.75%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.87%	90.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.90%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.58%	92.94%

Plants that contains it

• Acourtia carpholepis
• Acourtia nana
• Acourtia thurberi
• Acourtia turbinata
• Coreocarpus arizonicus

Cross-Links

• PubChem: 12314345
• LOTUS: LTS0093723
• wikiData: Q103813497