Grayanotoxin XVIII

Details

• Internal ID: ce545608-2eea-4db8-877a-11239045790e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Tertiary alcohols
• IUPAC Name: (1R,3R,4R,6S,8S,10R,13R,14R)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,14-tetrol
• SMILES (Canonical): CC1(C(CC2C1(C(CC34CC(CCC3C2=C)C(C4)(C)O)O)O)O)C
• SMILES (Isomeric): C[C@]1(C[C@]23C[C@H]1CC[C@H]2C(=C)[C@@H]4C[C@@H](C([C@]4([C@@H](C3)O)O)(C)C)O)O
• InChI: InChI=1S/C20H32O4/c1-11-13-6-5-12-8-19(13,10-18(12,4)23)9-16(22)20(24)14(11)7-15(21)17(20,2)3/h12-16,21-24H,1,5-10H2,2-4H3/t12-,13+,14+,15+,16-,18-,19-,20+/m1/s1
• InChI Key: AHMSDGIIEDDLQI-IQDQMAIWSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• 70474-76-9
• grayanotoxin-XVIII
• CHEMBL453541
• AKOS040734486
• (1R,3S,4R,6S,8S,10R,13R,14R)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,14-tetrol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9673	96.73%
Caco-2	-	0.5978	59.78%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4628	46.28%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9244	92.44%
OATP1B3 inhibitior	+	0.8608	86.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.8107	81.07%
P-glycoprotein inhibitior	-	0.8825	88.25%
P-glycoprotein substrate	-	0.5597	55.97%
CYP3A4 substrate	+	0.6227	62.27%
CYP2C9 substrate	+	0.5875	58.75%
CYP2D6 substrate	-	0.7710	77.10%
CYP3A4 inhibition	-	0.8768	87.68%
CYP2C9 inhibition	-	0.6451	64.51%
CYP2C19 inhibition	-	0.6716	67.16%
CYP2D6 inhibition	-	0.9377	93.77%
CYP1A2 inhibition	-	0.7479	74.79%
CYP2C8 inhibition	-	0.7562	75.62%
CYP inhibitory promiscuity	-	0.9296	92.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8371	83.71%
Skin irritation	+	0.5448	54.48%
Skin corrosion	-	0.9260	92.60%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3830	38.30%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.6908	69.08%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4837	48.37%
Acute Oral Toxicity (c)	I	0.5019	50.19%
Estrogen receptor binding	+	0.8785	87.85%
Androgen receptor binding	+	0.6248	62.48%
Thyroid receptor binding	+	0.6895	68.95%
Glucocorticoid receptor binding	+	0.8603	86.03%
Aromatase binding	+	0.7182	71.82%
PPAR gamma	-	0.5775	57.75%
Honey bee toxicity	-	0.8296	82.96%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9873	98.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.80%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.11%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.15%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.91%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.56%	97.25%

Plants that contains it

• Pieris japonica

Cross-Links

• PubChem: 44559345
• LOTUS: LTS0266797
• wikiData: Q104912324