Rhodotoxin

Details

• Internal ID: 1ecec994-52ce-4095-b8a9-b36c8297cae4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Grayanoids > Leucothol and grayanotoxane diterpenoids
• IUPAC Name: (3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyl-16-tetracyclo[11.2.1.01,10.04,8]hexadecanyl) acetate
• SMILES (Canonical): CC(=O)OC1C2CCC3C1(CC(C4(C(C3(C)O)CC(C4(C)C)O)O)O)CC2(C)O
• SMILES (Isomeric): CC(=O)OC1C2CCC3C1(CC(C4(C(C3(C)O)CC(C4(C)C)O)O)O)CC2(C)O
• InChI: InChI=1S/C22H36O7/c1-11(23)29-17-12-6-7-13-20(5,27)14-8-15(24)18(2,3)22(14,28)16(25)9-21(13,17)10-19(12,4)26/h12-17,24-28H,6-10H2,1-5H3
• InChI Key: NXCYBYJXCJWMRY-UHFFFAOYSA-N
• Popularity: 113 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₇
• Molecular Weight: 412.50 g/mol
• Exact Mass: 412.24610348 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.74
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• Acetyllandromedol
• Andromedotoxin
• GRAYANOTOXIN I
• Asebotoxin
• Rhodotoxin
• Rhodotoxine
• Acetylandromedol
• NSC26711
• GTX-I
• 4720-09-6
• NSC 26711
• NSC-26711
• Andromedol, acetate
• CHEMBL1971906
• Grayanotoxane-3,5,6,10,14,16-hexol, 14-acetate, (3.beta.,6.beta.,14R)-
• NXCYBYJXCJWMRY-UHFFFAOYSA-N
• G-I
• NCI60_002155
• 3,5,6,10,16-Pentahydroxygrayanotoxan-14-yl acetate #
• Grayanotoxane-3,6,10,14,16-hexol, 14-acetate, (3.beta.,6.beta.,14R)-
• WLN: L E5 B765 A 1B P BXTJ AOV1 DQ EQ F1 F1 GQ JQ J1 OQ O1
• (3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyl-16-tetracyclo[11.2.1.01,10.04,8]hexadecanyl) acetate
• 7,4,8,11,11a,12(1H)-hexol, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate (2S,3aS,4R,4aR,7R,8R,9aS,11R,11aR,12R)-
• 7,4,8,11,11a,12(1H)-hexol, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate, (2S,3aS,4R,4aR,7R,8R,9aS,11R,11aR,12R)-
• 7,9a-Methano-9aH-cyclopenta(b)-heptalene-2,4,8,11,11a,12(1H)-hexol, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate (2S,3aS,4R,4aR,7R,8R,9aS,11R,11aR,12R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9302	93.02%
Caco-2	-	0.6448	64.48%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7290	72.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9029	90.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8821	88.21%
BSEP inhibitior	-	0.7282	72.82%
P-glycoprotein inhibitior	-	0.7845	78.45%
P-glycoprotein substrate	-	0.7266	72.66%
CYP3A4 substrate	+	0.6750	67.50%
CYP2C9 substrate	-	0.8163	81.63%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.8460	84.60%
CYP2C9 inhibition	-	0.6112	61.12%
CYP2C19 inhibition	-	0.6449	64.49%
CYP2D6 inhibition	-	0.9630	96.30%
CYP1A2 inhibition	-	0.6144	61.44%
CYP2C8 inhibition	-	0.6512	65.12%
CYP inhibitory promiscuity	-	0.9835	98.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6888	68.88%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9533	95.33%
Skin irritation	+	0.5630	56.30%
Skin corrosion	-	0.9195	91.95%
Ames mutagenesis	-	0.6237	62.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4667	46.67%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6111	61.11%
skin sensitisation	-	0.7741	77.41%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4815	48.15%
Acute Oral Toxicity (c)	III	0.3676	36.76%
Estrogen receptor binding	+	0.8936	89.36%
Androgen receptor binding	+	0.6264	62.64%
Thyroid receptor binding	+	0.7166	71.66%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	+	0.7605	76.05%
PPAR gamma	-	0.5139	51.39%
Honey bee toxicity	-	0.6685	66.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9699	96.99%

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	95.60%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.24%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.80%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.44%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	90.72%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.32%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.30%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.73%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.24%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.06%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.57%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.36%	82.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.23%	85.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.16%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.85%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.79%	95.89%

Plants that contains it

• Leucothoe grayana
• Pieris japonica
• Rhododendron dauricum
• Rhododendron decorum
• Rhododendron degronianum
• Rhododendron japonoheptamerum

Cross-Links

• PubChem: 231125
• NPASS: NPC2572
• LOTUS: LTS0229731
• wikiData: Q105186950