[(3S,4R,6S,11R)-4-bromo-3-hydroxy-5,5,9-trimethyl-1-methylidenespiro[5.5]undec-8-en-11-yl] acetate

Details

• Internal ID: d8d75581-c552-4ef6-86ca-8f494aa7a64f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Chamigranes
• IUPAC Name: [(3S,4R,6S,11R)-4-bromo-3-hydroxy-5,5,9-trimethyl-1-methylidenespiro[5.5]undec-8-en-11-yl] acetate
• SMILES (Canonical): CC1=CCC2(C(C1)OC(=O)C)C(=C)CC(C(C2(C)C)Br)O
• SMILES (Isomeric): CC1=CC[C@]2([C@@H](C1)OC(=O)C)C(=C)C[C@@H]([C@@H](C2(C)C)Br)O
• InChI: InChI=1S/C17H25BrO3/c1-10-6-7-17(14(8-10)21-12(3)19)11(2)9-13(20)15(18)16(17,4)5/h6,13-15,20H,2,7-9H2,1,3-5H3/t13-,14+,15-,17+/m0/s1
• InChI Key: RSUGPKKDHKKQLW-QSJFSLAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₅BrO₃
• Molecular Weight: 357.30 g/mol
• Exact Mass: 356.09871 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.6027	60.27%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7153	71.53%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8967	89.67%
OATP1B3 inhibitior	+	0.9320	93.20%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8213	82.13%
P-glycoprotein inhibitior	-	0.8929	89.29%
P-glycoprotein substrate	-	0.8535	85.35%
CYP3A4 substrate	+	0.6265	62.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8510	85.10%
CYP3A4 inhibition	-	0.6322	63.22%
CYP2C9 inhibition	-	0.6830	68.30%
CYP2C19 inhibition	-	0.8068	80.68%
CYP2D6 inhibition	-	0.9425	94.25%
CYP1A2 inhibition	-	0.9095	90.95%
CYP2C8 inhibition	-	0.7584	75.84%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7449	74.49%
Carcinogenicity (trinary)	Non-required	0.5209	52.09%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.6923	69.23%
Skin irritation	-	0.5443	54.43%
Skin corrosion	-	0.9647	96.47%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7579	75.79%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5784	57.84%
skin sensitisation	+	0.5253	52.53%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5822	58.22%
Acute Oral Toxicity (c)	III	0.7010	70.10%
Estrogen receptor binding	-	0.6189	61.89%
Androgen receptor binding	-	0.5051	50.51%
Thyroid receptor binding	-	0.6491	64.91%
Glucocorticoid receptor binding	+	0.7302	73.02%
Aromatase binding	+	0.5614	56.14%
PPAR gamma	-	0.6699	66.99%
Honey bee toxicity	-	0.7835	78.35%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5705	57.05%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.56%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.25%	97.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.46%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.85%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.91%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.18%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.90%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.31%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.14%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163105869
• LOTUS: LTS0222198
• wikiData: Q105244877