(1S,2R,4R)-2-bromo-1-methyl-4-[3-[(1S,2R,3S,5S)-5-methyl-3-prop-1-en-2-yl-6-oxabicyclo[3.1.1]heptan-2-yl]prop-1-en-2-yl]cyclohexan-1-ol

Details

• Internal ID: 7ca6fdea-9dd7-424d-b207-406c70003c9f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,2R,4R)-2-bromo-1-methyl-4-[3-[(1S,2R,3S,5S)-5-methyl-3-prop-1-en-2-yl-6-oxabicyclo[3.1.1]heptan-2-yl]prop-1-en-2-yl]cyclohexan-1-ol
• SMILES (Canonical): CC(=C)C1CC2(CC(C1CC(=C)C3CCC(C(C3)Br)(C)O)O2)C
• SMILES (Isomeric): CC(=C)[C@H]1C[C@]2(C[C@@H]([C@@H]1CC(=C)[C@@H]3CC[C@]([C@@H](C3)Br)(C)O)O2)C
• InChI: InChI=1S/C20H31BrO2/c1-12(2)16-10-19(4)11-17(23-19)15(16)8-13(3)14-6-7-20(5,22)18(21)9-14/h14-18,22H,1,3,6-11H2,2,4-5H3/t14-,15-,16-,17+,18-,19+,20+/m1/s1
• InChI Key: NFNFPHXXILVTBW-VMJIZDNZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₁BrO₂
• Molecular Weight: 383.40 g/mol
• Exact Mass: 382.15074 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.01
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	-	0.5464	54.64%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Lysosomes	0.5056	50.56%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8772	87.72%
OATP1B3 inhibitior	+	0.9338	93.38%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8633	86.33%
P-glycoprotein inhibitior	-	0.7816	78.16%
P-glycoprotein substrate	-	0.6902	69.02%
CYP3A4 substrate	+	0.6155	61.55%
CYP2C9 substrate	-	0.7867	78.67%
CYP2D6 substrate	-	0.7847	78.47%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.6871	68.71%
CYP2C19 inhibition	-	0.7135	71.35%
CYP2D6 inhibition	-	0.8997	89.97%
CYP1A2 inhibition	-	0.8034	80.34%
CYP2C8 inhibition	-	0.5704	57.04%
CYP inhibitory promiscuity	-	0.8870	88.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8672	86.72%
Carcinogenicity (trinary)	Non-required	0.5680	56.80%
Eye corrosion	-	0.9795	97.95%
Eye irritation	-	0.8341	83.41%
Skin irritation	-	0.6642	66.42%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3772	37.72%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5478	54.78%
skin sensitisation	-	0.6561	65.61%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5232	52.32%
Acute Oral Toxicity (c)	III	0.6490	64.90%
Estrogen receptor binding	+	0.7491	74.91%
Androgen receptor binding	+	0.5406	54.06%
Thyroid receptor binding	+	0.5966	59.66%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.5530	55.30%
PPAR gamma	-	0.5064	50.64%
Honey bee toxicity	-	0.8000	80.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9823	98.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.05%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.48%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.80%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.98%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.40%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.58%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.14%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.11%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.02%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.89%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.85%	92.94%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.40%	96.38%
CHEMBL1871	P10275	Androgen Receptor	83.70%	96.43%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.51%	93.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.45%	85.30%
CHEMBL259	P32245	Melanocortin receptor 4	82.45%	95.38%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.34%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.49%	96.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.28%	82.69%
CHEMBL4072	P07858	Cathepsin B	80.98%	93.67%
CHEMBL340	P08684	Cytochrome P450 3A4	80.43%	91.19%

Plants that contains it

• Anethum graveolens
• Cymbidium aloifolium
• Delphinium dictyocarpum
• Ladeania juncea
• Ligularia atroviolacea
• Scutellaria glabra
• Trifolium pannonicum

Cross-Links

• PubChem: 10547984
• NPASS: NPC194314
• LOTUS: LTS0242201
• wikiData: Q105178565