(1R,5aS,6R,7R,8R,9aR,9bS)-7-chloro-6-[(3S)-3,4-dimethylpent-4-enyl]-6,9a-dimethyl-1,3,5,5a,7,8,9,9b-octahydrobenzo[g][2]benzofuran-1,8-diol

Details

• Internal ID: e09b5540-0afd-4a6a-b7f3-580508cc1fd7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,5aS,6R,7R,8R,9aR,9bS)-7-chloro-6-[(3S)-3,4-dimethylpent-4-enyl]-6,9a-dimethyl-1,3,5,5a,7,8,9,9b-octahydrobenzo[g][2]benzofuran-1,8-diol
• SMILES (Canonical): CC(CCC1(C2CC=C3COC(C3C2(CC(C1Cl)O)C)O)C)C(=C)C
• SMILES (Isomeric): C[C@@H](CC[C@@]1([C@H]2CC=C3CO[C@H]([C@H]3[C@@]2(C[C@H]([C@@H]1Cl)O)C)O)C)C(=C)C
• InChI: InChI=1S/C21H33ClO3/c1-12(2)13(3)8-9-20(4)16-7-6-14-11-25-19(24)17(14)21(16,5)10-15(23)18(20)22/h6,13,15-19,23-24H,1,7-11H2,2-5H3/t13-,15+,16+,17-,18-,19+,20+,21+/m0/s1
• InChI Key: YIKMJRPKQBPFHJ-HGUFDRQISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₃ClO₃
• Molecular Weight: 368.90 g/mol
• Exact Mass: 368.2118226 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.27
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.5686	56.86%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6626	66.26%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.8689	86.89%
OATP1B3 inhibitior	+	0.9150	91.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.7338	73.38%
P-glycoprotein inhibitior	-	0.7905	79.05%
P-glycoprotein substrate	+	0.5146	51.46%
CYP3A4 substrate	+	0.6510	65.10%
CYP2C9 substrate	-	0.6127	61.27%
CYP2D6 substrate	-	0.7884	78.84%
CYP3A4 inhibition	+	0.5145	51.45%
CYP2C9 inhibition	-	0.7826	78.26%
CYP2C19 inhibition	-	0.7570	75.70%
CYP2D6 inhibition	-	0.8416	84.16%
CYP1A2 inhibition	-	0.7709	77.09%
CYP2C8 inhibition	-	0.6229	62.29%
CYP inhibitory promiscuity	-	0.6485	64.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8913	89.13%
Carcinogenicity (trinary)	Non-required	0.5097	50.97%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9691	96.91%
Skin irritation	-	0.5463	54.63%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.5478	54.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7251	72.51%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5024	50.24%
skin sensitisation	-	0.8258	82.58%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6879	68.79%
Acute Oral Toxicity (c)	III	0.5936	59.36%
Estrogen receptor binding	+	0.6687	66.87%
Androgen receptor binding	+	0.6153	61.53%
Thyroid receptor binding	+	0.7940	79.40%
Glucocorticoid receptor binding	+	0.7102	71.02%
Aromatase binding	+	0.5524	55.24%
PPAR gamma	+	0.5546	55.46%
Honey bee toxicity	-	0.7287	72.87%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	98.87%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.58%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.55%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.81%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.45%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.15%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.76%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.17%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.56%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.81%	100.00%

Plants that contains it

• Decalobanthus mammosus

Cross-Links

• PubChem: 162972655
• LOTUS: LTS0224219
• wikiData: Q105292997