Scyllatoxin

Basic Info

Common NameScyllatoxin(F04708)
2D Structure
Description

Scyllatoxin is a peptide toxin produced by the Yellow scorpion (Leiurus quinquestriatus hebraeus). It blocks small conductance calcium-activated potassium channels. (L1061)

FRCD IDF04708
CAS Number142948-19-4
PubChem CID71311759
FormulaC142H243N45O39S7
IUPAC Name

None

InChI Key

MXWDLLUGULWYIQ-BFRWRHKQSA-N

InChI

InChI=1S/C142H243N45O39S7/c1-17-75(14)112(139(225)159-59-108(194)163-95(55-110(197)198)130(216)164-80(32-22-25-42-144)121(207)180-98(62-227)135(221)168-85(37-39-109(195)196)123(209)183-102(66-231)137(223)186-111(74(12)13)140(226)170-81(33-23-26-43-145)119(205)171-87(113(149)199)53-78-56-154-68-160-78)187-138(224)103(67-232)182-117(203)79(31-21-24-41-143)161-106(192)57-157-115(201)88(47-69(2)3)173-125(211)90(49-71(6)7)162-107(193)58-158-116(202)89(48-70(4)5)174-131(217)96(60-188)178-120(206)83(35-28-45-156-142(152)153)166-133(219)100(64-229)185-132(218)97(61-189)179-127(213)92(51-73(10)11)175-122(208)84(36-38-104(147)190)167-134(220)99(63-228)181-124(210)86(40-46-233-16)169-118(204)82(34-27-44-155-141(150)151)165-126(212)91(50-72(8)9)176-129(215)94(54-105(148)191)177-136(222)101(65-230)184-128(214)93(172-114(200)76(15)146)52-77-29-19-18-20-30-77/h18-20,29-30,56,68-76,79-103,111-112,188-189,227-232H,17,21-28,31-55,57-67,143-146H2,1-16H3,(H2,147,190)(H2,148,191)(H2,149,199)(H,154,160)(H,157,201)(H,158,202)(H,159,225)(H,161,192)(H,162,193)(H,163,194)(H,164,216)(H,165,212)(H,166,219)(H,167,220)(H,168,221)(H,169,204)(H,170,226)(H,171,205)(H,172,200)(H,173,211)(H,174,217)(H,175,208)(H,176,215)(H,177,222)(H,178,206)(H,179,213)(H,180,207)(H,181,210)(H,182,203)(H,183,209)(H,184,214)(H,185,218)(H,186,223)(H,187,224)(H,195,196)(H,197,198)(H4,150,151,155)(H4,152,153,156)/t75-,76-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,111-,112-/m0/s1

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CS)C(=O)NC(CCC(=O)O)C(=O)NC(CS)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC(CC1=CNC=N1)C(=O)N)NC(=O)C(CS)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(CCCNC(=N)N)NC(=O)C(CS)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)N)NC(=O)C(CS)NC(=O)C(CCSC)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)N)NC(=O)C(CS)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(C)N

Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](C)N

Synonyms
        
            Scyllatoxin, recombinant, expressed in E. coli, >=95% (HPLC), lyophilized powder
        
            Scyllatoxin
        
            Leiurotoxin I
        
            LeTx I scorpion toxin
        
            116235-63-3
        
            142948-19-4
        
            Leiurotoxin 1
Classifies
                

                  
                    Animal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic Polymers
ClassPolypeptides
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentPolypeptides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPolypeptide - Alpha peptide - Arginine or derivatives - Phenylalanine or derivatives - Histidine or derivatives - Glutamic acid or derivatives - Glutamine or derivatives - Isoleucine or derivatives - Aspartic acid or derivatives - Asparagine or derivatives - Methionine or derivatives - Leucine or derivatives - Valine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Cysteine or derivatives - Serine or derivatives - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Imidazolyl carboxylic acid derivative - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Fatty amide - N-acyl-amine - Fatty acyl - Benzenoid - Imidazole - Azole - Heteroaromatic compound - Guanidine - Secondary carboxylic acid amide - Primary carboxylic acid amide - Carboxamide group - Amino acid - Amino acid or derivatives - Carboximidamide - Sulfenyl compound - Azacycle - Dialkylthioether - Carboxylic acid derivative - Organoheterocyclic compound - Thioether - Carboxylic acid - Alkylthiol - Primary amine - Organic nitrogen compound - Hydrocarbon derivative - Imine - Carbonyl group - Alcohol - Primary aliphatic amine - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxide - Amine - Primary alcohol - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.

Properties

Property NameProperty Value
Molecular Weight3429.202
Hydrogen Bond Donor Count54
Hydrogen Bond Acceptor Count53
Rotatable Bond Count121
Complexity7500
Monoisotopic Mass3426.646
Exact Mass3427.649
XLogP-12.8
Formal Charge0
Heavy Atom Count233
Defined Atom Stereocenter Count29
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9745
Human Intestinal AbsorptionHIA+0.9375
Caco-2 PermeabilityCaco2-0.7468
P-glycoprotein SubstrateSubstrate0.8465
P-glycoprotein InhibitorNon-inhibitor0.8571
Non-inhibitor0.9927
Renal Organic Cation TransporterNon-inhibitor0.8476
Distribution
Subcellular localizationMitochondria0.4672
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8216
CYP450 2D6 SubstrateNon-substrate0.7717
CYP450 3A4 SubstrateNon-substrate0.5917
CYP450 1A2 InhibitorNon-inhibitor0.8410
CYP450 2C9 InhibitorNon-inhibitor0.8182
CYP450 2D6 InhibitorNon-inhibitor0.8905
CYP450 2C19 InhibitorNon-inhibitor0.8099
CYP450 3A4 InhibitorNon-inhibitor0.8728
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9856
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9825
Non-inhibitor0.7850
AMES ToxicityNon AMES toxic0.7358
CarcinogensNon-carcinogens0.9171
Fish ToxicityHigh FHMT0.9591
Tetrahymena Pyriformis ToxicityHigh TPT0.9908
Honey Bee ToxicityLow HBT0.7494
BiodegradationNot ready biodegradable0.9780
Acute Oral ToxicityIII0.5899
Carcinogenicity (Three-class)Non-required0.6090
Model Value Unit
Absorption
Aqueous solubility-2.8841LogS
Caco-2 Permeability-0.4138LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7446LD50, mol/kg
Fish Toxicity1.7280pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4370pIGC50, ug/L

Targets

Target Details

Small conductance calcium-activated potassium channel protein 2

General Function:
Small conductance calcium-activated potassium channel activity
Specific Function:
Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to the slow component of synaptic afterhyperpolarization. The channel is blocked by apamin.
Gene Name:
KCNN2
Uniprot ID:
Q9H2S1
Molecular Weight:
63759.03 Da
Mechanism of Action:
Scyllatoxin blocks small conductance calcium-activated potassium channels. This inhibits the slow after-hyperpolarisation that follows an action potential in some nerve cells.
References
  1. Wikipedia. Scyllatoxin. Last Updated 5 April 2009. : http://en.wikipedia.org/wiki/Scyllatoxin
Target Details

Small conductance calcium-activated potassium channel protein 3

General Function:
Small conductance calcium-activated potassium channel activity
Specific Function:
Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to the slow component of synaptic afterhyperpolarization. The channel is blocked by apamin.
Gene Name:
KCNN3
Uniprot ID:
Q9UGI6
Molecular Weight:
82025.305 Da
Mechanism of Action:
Scyllatoxin blocks small conductance calcium-activated potassium channels. This inhibits the slow after-hyperpolarisation that follows an action potential in some nerve cells.
References
  1. Wikipedia. Scyllatoxin. Last Updated 5 April 2009. : http://en.wikipedia.org/wiki/Scyllatoxin
Target Details

Small conductance calcium-activated potassium channel protein 1

General Function:
Small conductance calcium-activated potassium channel activity
Specific Function:
Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to the slow component of synaptic afterhyperpolarization. The channel is blocked by apamin (By similarity).
Gene Name:
KCNN1
Uniprot ID:
Q92952
Molecular Weight:
59986.87 Da
Mechanism of Action:
Scyllatoxin blocks small conductance calcium-activated potassium channels. This inhibits the slow after-hyperpolarisation that follows an action potential in some nerve cells.
References
  1. Wikipedia. Scyllatoxin. Last Updated 5 April 2009. : http://en.wikipedia.org/wiki/Scyllatoxin