(1S,10S,13R,15S)-9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.02,7.013,15]pentadeca-2,4,6-trien-3-ol

Details

• Internal ID: d101d240-daf1-4535-967b-b72e3aff2525
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: (1S,10S,13R,15S)-9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.02,7.013,15]pentadeca-2,4,6-trien-3-ol
• SMILES (Canonical): CCCCCC1=CC(=C2C3C(CCC4(C3O4)C)C(OC2=C1)(C)C)O
• SMILES (Isomeric): CCCCCC1=CC(=C2[C@@H]3[C@H](CC[C@@]4([C@H]3O4)C)C(OC2=C1)(C)C)O
• InChI: InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3/t14-,17-,19-,21+/m0/s1
• InChI Key: VSQGBNUBIDZRPJ-HIUUTZCYSA-N
• Popularity: 0 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): 42.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.95
• H-Bond Acceptor: 3
• 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	+	0.9869	98.69%
Caco-2	+	0.8752	87.52%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6202	62.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7397	73.97%
P-glycoprotein inhibitior	-	0.5294	52.94%
P-glycoprotein substrate	-	0.5397	53.97%
CYP3A4 substrate	+	0.6920	69.20%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	+	0.4392	43.92%
CYP3A4 inhibition	-	0.9426	94.26%
CYP2C9 inhibition	-	0.7036	70.36%
CYP2C19 inhibition	-	0.7006	70.06%
CYP2D6 inhibition	-	0.8745	87.45%
CYP1A2 inhibition	-	0.6969	69.69%
CYP2C8 inhibition	+	0.7681	76.81%
CYP inhibitory promiscuity	-	0.7659	76.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9526	95.26%
Skin irritation	-	0.7397	73.97%
Skin corrosion	-	0.9174	91.74%
Ames mutagenesis	-	0.7837	78.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4211	42.11%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.7257	72.57%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6502	65.02%
Acute Oral Toxicity (c)	III	0.6777	67.77%
Estrogen receptor binding	+	0.7363	73.63%
Androgen receptor binding	+	0.8109	81.09%
Thyroid receptor binding	+	0.6895	68.95%
Glucocorticoid receptor binding	+	0.8260	82.60%
Aromatase binding	+	0.7013	70.13%
PPAR gamma	+	0.7290	72.90%
Honey bee toxicity	-	0.9033	90.33%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7147	71.47%
Fish aquatic toxicity	+	0.9404	94.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	224 nM	Ki	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	335 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL240	Q12809	HERG	98.46%	89.76%
CHEMBL230	P35354	Cyclooxygenase-2	97.68%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.00%	92.86%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.65%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.59%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.16%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.46%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.61%	100.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	86.26%	92.68%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.14%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.61%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.04%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.92%	95.50%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.84%	99.18%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.52%	100.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	83.14%	92.08%
CHEMBL233	P35372	Mu opioid receptor	83.13%	97.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.57%	100.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.57%	96.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.52%	96.25%
CHEMBL2996	Q05655	Protein kinase C delta	81.42%	97.79%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.70%	90.24%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.52%	96.95%

Plants that contains it

• Aragoa cundinamarcensis
• Cannabis sativa
• Plantago maritima

Cross-Links

• PubChem: 163190002
• LOTUS: LTS0011573
• wikiData: Q104394547