(1R,3R,6S,8R,11R)-8-bromo-4,11,12,12-tetramethyl-7-oxatricyclo[6.3.1.01,6]dodeca-4,9-diene-3,11-diol

Details

• Internal ID: 54769d7b-dcb3-42aa-b002-d64158232b58
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Chamigranes
• IUPAC Name: (1R,3R,6S,8R,11R)-8-bromo-4,11,12,12-tetramethyl-7-oxatricyclo[6.3.1.01,6]dodeca-4,9-diene-3,11-diol
• SMILES (Canonical): CC1=CC2C3(CC1O)C(C(O2)(C=CC3(C)O)Br)(C)C
• SMILES (Isomeric): CC1=C[C@H]2[C@]3(C[C@H]1O)[C@](C=C[C@@](C3(C)C)(O2)Br)(C)O
• InChI: InChI=1S/C15H21BrO3/c1-9-7-11-14(8-10(9)17)12(2,3)15(16,19-11)6-5-13(14,4)18/h5-7,10-11,17-18H,8H2,1-4H3/t10-,11+,13-,14+,15+/m1/s1
• InChI Key: AZEHQKRQHNFRMW-VEESAYDSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁BrO₃
• Molecular Weight: 329.23 g/mol
• Exact Mass: 328.06741 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	-	0.5382	53.82%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4812	48.12%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9086	90.86%
OATP1B3 inhibitior	+	0.9542	95.42%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7884	78.84%
P-glycoprotein inhibitior	-	0.9394	93.94%
P-glycoprotein substrate	-	0.8538	85.38%
CYP3A4 substrate	+	0.5826	58.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8110	81.10%
CYP3A4 inhibition	-	0.8966	89.66%
CYP2C9 inhibition	-	0.6631	66.31%
CYP2C19 inhibition	-	0.7356	73.56%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.7974	79.74%
CYP2C8 inhibition	-	0.7527	75.27%
CYP inhibitory promiscuity	+	0.6695	66.95%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8672	86.72%
Carcinogenicity (trinary)	Danger	0.3767	37.67%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.8854	88.54%
Skin irritation	-	0.6604	66.04%
Skin corrosion	-	0.9044	90.44%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6764	67.64%
Micronuclear	-	0.6841	68.41%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.6499	64.99%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6081	60.81%
Acute Oral Toxicity (c)	III	0.3800	38.00%
Estrogen receptor binding	+	0.5705	57.05%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5218	52.18%
Glucocorticoid receptor binding	+	0.6544	65.44%
Aromatase binding	+	0.5828	58.28%
PPAR gamma	-	0.4868	48.68%
Honey bee toxicity	-	0.8808	88.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9652	96.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.14%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.24%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.40%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.37%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.47%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.41%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.35%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.12%	94.00%

Plants that contains it

• Eleutherococcus giraldii
• Lespedeza davidii
• Solanum aethiopicum
• Tectona grandis

Cross-Links

• PubChem: 21637490
• NPASS: NPC212442
• LOTUS: LTS0117542
• wikiData: Q104921634