Clusianone

Details

• Internal ID: 9a5b4531-9403-4981-8e04-048d186159c3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1S,3E,5R,7R)-3-[hydroxy(phenyl)methylidene]-6,6-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]nonane-2,4,9-trione
• SMILES (Canonical): CC(=CCC1CC2(C(=O)C(=C(C3=CC=CC=C3)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC=C(C)C)C
• SMILES (Isomeric): CC(=CC[C@@H]1C[C@@]2(C(=O)/C(=C(/C3=CC=CC=C3)\O)/C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)CC=C(C)C)C
• InChI: InChI=1S/C33H42O4/c1-21(2)14-15-25-20-32(18-16-22(3)4)28(35)26(27(34)24-12-10-9-11-13-24)29(36)33(30(32)37,31(25,7)8)19-17-23(5)6/h9-14,16-17,25,34H,15,18-20H2,1-8H3/b27-26+/t25-,32-,33+/m1/s1
• InChI Key: KLFBRRJTELLZLW-SPNPYKNRSA-N
• Popularity: 43 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₄
• Molecular Weight: 502.70 g/mol
• Exact Mass: 502.30830982 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 9.10
• Atomic LogP (AlogP): 7.76
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• epi-Cusianone
• 6-epi-clusianone, (rel)-
• Clusianone
• CHEMBL459015

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6036	60.36%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8019	80.19%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9046	90.46%
OATP1B3 inhibitior	+	0.9070	90.70%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9849	98.49%
P-glycoprotein inhibitior	+	0.6962	69.62%
P-glycoprotein substrate	-	0.6283	62.83%
CYP3A4 substrate	+	0.5620	56.20%
CYP2C9 substrate	-	0.7931	79.31%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.8612	86.12%
CYP2C9 inhibition	-	0.6380	63.80%
CYP2C19 inhibition	-	0.6482	64.82%
CYP2D6 inhibition	-	0.8735	87.35%
CYP1A2 inhibition	-	0.7162	71.62%
CYP2C8 inhibition	-	0.5966	59.66%
CYP inhibitory promiscuity	-	0.5492	54.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8242	82.42%
Carcinogenicity (trinary)	Non-required	0.6510	65.10%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8556	85.56%
Skin irritation	-	0.5750	57.50%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7730	77.30%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7177	71.77%
skin sensitisation	+	0.5500	55.00%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6499	64.99%
Acute Oral Toxicity (c)	III	0.6612	66.12%
Estrogen receptor binding	+	0.7499	74.99%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	+	0.6522	65.22%
Glucocorticoid receptor binding	+	0.7034	70.34%
Aromatase binding	+	0.6989	69.89%
PPAR gamma	+	0.7301	73.01%
Honey bee toxicity	-	0.8579	85.79%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.05%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.49%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.09%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	86.32%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.98%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	81.51%	83.82%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.36%	94.62%

Plants that contains it

• Clusia fluminensis
• Clusia sandiensis
• Clusia spiritu-sanctensis

Cross-Links

• PubChem: 44593352
• LOTUS: LTS0054608
• wikiData: Q104397467