(1S,5S,7S)-9-acetyl-8-hydroxy-4,4-dimethyl-7-(3-methylbut-2-enyl)tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione

Details

• Internal ID: 59dcfc60-f4ce-4968-8abf-1335510f6ba3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids
• IUPAC Name: (1S,5S,7S)-9-acetyl-8-hydroxy-4,4-dimethyl-7-(3-methylbut-2-enyl)tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione
• SMILES (Canonical): CC(=CCC12CC3C(CCC3(C1=O)C(=O)C(=C2O)C(=O)C)(C)C)C
• SMILES (Isomeric): CC(=CC[C@@]12C[C@@H]3[C@](C1=O)(CCC3(C)C)C(=O)C(=C2O)C(=O)C)C
• InChI: InChI=1S/C20H26O4/c1-11(2)6-7-19-10-13-18(4,5)8-9-20(13,17(19)24)16(23)14(12(3)21)15(19)22/h6,13,22H,7-10H2,1-5H3/t13-,19-,20+/m0/s1
• InChI Key: HCSXVHTVHSOETR-QTJFZDIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7573	75.73%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7605	76.05%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.8684	86.84%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6810	68.10%
P-glycoprotein inhibitior	-	0.8571	85.71%
P-glycoprotein substrate	-	0.7634	76.34%
CYP3A4 substrate	+	0.5764	57.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8685	86.85%
CYP3A4 inhibition	-	0.8253	82.53%
CYP2C9 inhibition	-	0.6867	68.67%
CYP2C19 inhibition	-	0.9104	91.04%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.7867	78.67%
CYP2C8 inhibition	-	0.8207	82.07%
CYP inhibitory promiscuity	-	0.8968	89.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6260	62.60%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.6538	65.38%
Skin irritation	+	0.5463	54.63%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5126	51.26%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5872	58.72%
skin sensitisation	-	0.5320	53.20%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4603	46.03%
Acute Oral Toxicity (c)	III	0.3146	31.46%
Estrogen receptor binding	+	0.6872	68.72%
Androgen receptor binding	-	0.5445	54.45%
Thyroid receptor binding	+	0.5948	59.48%
Glucocorticoid receptor binding	+	0.5858	58.58%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8449	84.49%
Honey bee toxicity	-	0.8515	85.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	97.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.39%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	90.10%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.38%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.76%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.71%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.12%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.14%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.21%	97.25%

Plants that contains it

• Harrisonia abyssinica

Cross-Links

• PubChem: 163090115
• LOTUS: LTS0195326
• wikiData: Q105025969