Saxitoxin

Details

• Internal ID: bb4fe311-f7e6-4559-a2be-4af908ffc30e
• Taxonomy: Phenylpropanoids and polyketides > Saxitoxins, gonyautoxins, and derivatives
• IUPAC Name: [(3aS,4R,10aS)-2,6-diamino-10,10-dihydroxy-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• SMILES (Canonical): C1CN2C(=NC(C3C2(C1(O)O)NC(=N3)N)COC(=O)N)N
• SMILES (Isomeric): C1CN2C(=N[C@H]([C@H]3[C@]2(C1(O)O)NC(=N3)N)COC(=O)N)N
• InChI: InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4-,5-,10-/m0/s1
• InChI Key: RPQXVSUAYFXFJA-HGRQIUPRSA-N
• Popularity: 1,364 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₇N₇O₄
• Molecular Weight: 299.29 g/mol
• Exact Mass: 299.13420205 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -4.60
• Atomic LogP (AlogP): -3.85
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• 35523-89-8
• Saxitoxin-t
• Gonyaulax catenella poison
• Saxidomus giganteus poison
• Saxitoxin hydrate
• Saxitoxin-3H
• Mytilus californianus poison
• CHEBI:34970
• Q0638E899B
• [(3aS,4R,10aS)-10,10-dihydroxy-2,6-diiminooctahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2,6-diamino-4-(((amino-carbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-, (3aS-(3a-alpha,4-alpha,10aR*))
• 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2,6-diamino-4-(((aminocarbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-, (3aS,4R,10aS)-
• 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2,6-diamino-4-(((aminocarbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-, labeled with tritium, (3aS-(3aalpha,4alpha,10aR*))-
• 73603-72-2
• Saxitoxin (8CI)
• (+)-Saxitoxin
• SAXITOXIN [MI]
• 11017-04-2
• D0P8TL
• SAXITOXIN (HYDRATE)
• SCHEMBL49687
• CHEMBL501134
• GTPL2625
• DTXSID3074313
• SCHEMBL13028580
• SCHEMBL22829661
• UNII-Q0638E899B
• BDBM190233
• US9174999, Table 1, Compound 1
• [(3aS,4R,10aS)-2,6-diamino-10,10-dihydroxy-3a,4,8,9-tetrahydro-3H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2,6-diamino-4-(((aminocarbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-, (3aS-(3aalpha,4alpha,10aR*))-
• LS-139450
• S-1900
• Q412694
• Saxitoxin in acetic acid (determination in mussel), BCR(R) certified Reference Material
• [(3aS,4R,10aS)-2,6-diamino-10,10-dihydroxy-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• [(R,7aS,7bS)-2-amino-7,7-dihydroxy--imino-H,H,H,1H,5H,6H,7H,7bH-pyrrolo[1,2-c]purin--yl]methyl carbamate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6500	65.00%
Caco-2	-	0.7834	78.34%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5414	54.14%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9554	95.54%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7706	77.06%
P-glycoprotein inhibitior	-	0.8882	88.82%
P-glycoprotein substrate	-	0.5329	53.29%
CYP3A4 substrate	+	0.5508	55.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7201	72.01%
CYP3A4 inhibition	-	0.9770	97.70%
CYP2C9 inhibition	-	0.8853	88.53%
CYP2C19 inhibition	-	0.8566	85.66%
CYP2D6 inhibition	-	0.8662	86.62%
CYP1A2 inhibition	-	0.8234	82.34%
CYP2C8 inhibition	-	0.8519	85.19%
CYP inhibitory promiscuity	-	0.9832	98.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9801	98.01%
Skin irritation	-	0.7506	75.06%
Skin corrosion	-	0.9198	91.98%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7040	70.40%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8164	81.64%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6246	62.46%
Acute Oral Toxicity (c)	I	0.7869	78.69%
Estrogen receptor binding	+	0.7801	78.01%
Androgen receptor binding	+	0.6157	61.57%
Thyroid receptor binding	+	0.6633	66.33%
Glucocorticoid receptor binding	+	0.6490	64.90%
Aromatase binding	+	0.6283	62.83%
PPAR gamma	+	0.7449	74.49%
Honey bee toxicity	-	0.8869	88.69%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.9360	93.60%

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	98.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.92%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.92%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.93%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.89%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.62%	97.25%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	82.45%	92.32%
CHEMBL5028	O14672	ADAM10	82.00%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.23%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.75%	93.04%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.70%	97.53%

Plants that contains it

• Aucklandia costus
• Eleutherococcus sessiliflorus
• Ruta graveolens
• Ruta microcarpa
• Taiwania cryptomerioides

Cross-Links

• PubChem: 56947150
• NPASS: NPC305648