Cannabielsoin

Details

• Internal ID: 88f95f8e-dc5c-4747-b905-e0c7e8468e68
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Aromatic monoterpenoids
• IUPAC Name: (5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
• SMILES (Canonical): CCCCCC1=CC(=C2C3C(CCC(C3OC2=C1)(C)O)C(=C)C)O
• SMILES (Isomeric): CCCCCC1=CC(=C2[C@H]3[C@@H](CC[C@]([C@H]3OC2=C1)(C)O)C(=C)C)O
• InChI: InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1
• InChI Key: RBEAVAMWZAJWOI-MTOHEIAKSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Cannabielsoin A
• 52025-76-0
• 2ERD6V6652
• (5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
• CANNABIELSOIN I
• UNII-2ERD6V6652
• SCHEMBL13214152
• DTXSID50966364
• RBEAVAMWZAJWOI-MTOHEIAKSA-N
• C20218
• 1,6-DIBENZOFURANDIOL, 5A,6,7,8,9,9A-HEXAHYDRO-6-METHYL-9-(1-METHYLETHENYL)-3-PENTYL-, (5AS,6S,9R,9AR)-
• 1,6-DIBENZOFURANDIOL, 5A,6,7,8,9,9A-HEXAHYDRO-6-METHYL-9-(1-METHYLETHENYL)-3-PENTYL-, (5AS-(5A.ALPHA.,6.ALPHA.,9.ALPHA.,9A.ALPHA.))-
• 1,6-Dibenzofurandiol, 5a,6,7,8,9,9a-hexahydro-6-methyl-9-(1-methylethenyl)-3-pentyl-, (5aS-(5aalpha,6alpha,9alpha,9aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.6913	69.13%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5131	51.31%
OATP2B1 inhibitior	-	0.7210	72.10%
OATP1B1 inhibitior	+	0.8577	85.77%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7223	72.23%
P-glycoprotein inhibitior	-	0.7054	70.54%
P-glycoprotein substrate	+	0.5922	59.22%
CYP3A4 substrate	+	0.6445	64.45%
CYP2C9 substrate	-	0.5764	57.64%
CYP2D6 substrate	+	0.4156	41.56%
CYP3A4 inhibition	+	0.5660	56.60%
CYP2C9 inhibition	-	0.6129	61.29%
CYP2C19 inhibition	+	0.5856	58.56%
CYP2D6 inhibition	-	0.8462	84.62%
CYP1A2 inhibition	+	0.5906	59.06%
CYP2C8 inhibition	+	0.5624	56.24%
CYP inhibitory promiscuity	+	0.7711	77.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4823	48.23%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.6350	63.50%
Skin corrosion	-	0.9086	90.86%
Ames mutagenesis	-	0.6707	67.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.3951	39.51%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7220	72.20%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4629	46.29%
Acute Oral Toxicity (c)	III	0.4611	46.11%
Estrogen receptor binding	+	0.7538	75.38%
Androgen receptor binding	+	0.7388	73.88%
Thyroid receptor binding	+	0.7553	75.53%
Glucocorticoid receptor binding	+	0.7518	75.18%
Aromatase binding	+	0.7278	72.78%
PPAR gamma	+	0.8908	89.08%
Honey bee toxicity	-	0.9246	92.46%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6542	65.42%
Fish aquatic toxicity	+	0.9922	99.22%

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	98.30%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.95%	97.25%
CHEMBL240	Q12809	HERG	96.20%	89.76%
CHEMBL2581	P07339	Cathepsin D	94.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.14%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.83%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.76%	93.40%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.50%	92.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.66%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.53%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.89%	92.62%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.57%	92.86%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.10%	96.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.94%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.46%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.43%	95.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.82%	94.80%
CHEMBL233	P35372	Mu opioid receptor	83.57%	97.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.36%	100.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.08%	80.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.80%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.15%	95.89%
CHEMBL5203	P33316	dUTP pyrophosphatase	81.12%	99.18%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.89%	96.95%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.79%	90.24%
CHEMBL2996	Q05655	Protein kinase C delta	80.20%	97.79%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 162113
• LOTUS: LTS0199004
• wikiData: Q22668702