Arcaine

Details

• Internal ID: 76076cb8-1042-4214-8050-7e64eae133d0
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Guanidines
• IUPAC Name: 2-[4-(diaminomethylideneamino)butyl]guanidine
• InChI: InChI=1S/C6H16N6/c7-5(8)11-3-1-2-4-12-6(9)10/h1-4H2,(H4,7,8,11)(H4,9,10,12)
• InChI Key: HGMDNMBBCKDWTQ-UHFFFAOYSA-N
• Popularity: 156 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₆N₆
• Molecular Weight: 172.23 g/mol
• Exact Mass: 172.14364454 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 2
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 1,4-Diguanidinobutane
• Tetramethylenediguanide
• 544-05-8
• N,N'''-1,4-Butanediylbisguanidine
• 2-[4-(diaminomethylideneamino)butyl]guanidine
• 1-(4-guanidinobutyl)guanidine
• CHEMBL102740
• CHEBI:16652
• 1,1'-(butane-1,4-diyl)diguanidine
• Arcain
• 1-(4-carbamimidamidobutyl)guanidine
• Guanidine, N,N'''-1,4-butanediylbis-
• Spectrum_001819
• Tocris-0389
• Prestwick0_000876
• Prestwick1_000876
• Prestwick2_000876
• Prestwick3_000876
• Spectrum2_000601
• Spectrum3_001100
• Spectrum4_001929
• Spectrum5_001638
• Lopac-A-0384
• Biomol-NT_000178
• C03047
• Lopac0_000062
• BSPBio_000951
• BSPBio_002780
• KBioGR_002278
• KBioSS_002321
• DivK1c_000355
• SCHEMBL303546
• SPBio_000502
• SPBio_002872
• BPBio1_001047
• BPBio1_001168
• GTPL4137
• BDBM86165
• KBio1_000355
• KBio2_002319
• KBio2_004887
• KBio2_007455
• KBio3_002000
• DTXSID80110030
• NINDS_000355
• 1,1'-Butane-1,4-diyldiguanidine
• CAS_2227
• NSC_2227
• CCG-204157
• SDCCGMLS-0066569.P001
• SDCCGSBI-0050050.P003
• IDI1_000355
• NCGC00015028-01
• NCGC00015028-02
• NCGC00015028-03
• NCGC00015028-04
• NCGC00015028-05
• NCGC00015028-06
• NCGC00015028-13
• NCGC00024568-01
• NCGC00024568-02
• NCGC00024568-03
• CAS-14923-17-2
• AB00053729
• A-8340
• 2-{4-[(diaminomethylidene)amino]butyl}guanidine
• Q27074499

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8765	87.65%
Caco-2	+	0.5699	56.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Lysosomes	0.4764	47.64%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9602	96.02%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9523	95.23%
P-glycoprotein inhibitior	-	0.9785	97.85%
P-glycoprotein substrate	-	0.9415	94.15%
CYP3A4 substrate	-	0.7921	79.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6925	69.25%
CYP3A4 inhibition	-	0.9649	96.49%
CYP2C9 inhibition	-	0.9470	94.70%
CYP2C19 inhibition	-	0.9421	94.21%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8772	87.72%
CYP2C8 inhibition	-	0.9828	98.28%
CYP inhibitory promiscuity	-	0.9635	96.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5744	57.44%
Eye corrosion	-	0.9081	90.81%
Eye irritation	+	0.9264	92.64%
Skin irritation	+	0.6387	63.87%
Skin corrosion	+	0.7599	75.99%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7337	73.37%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7330	73.30%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.7849	78.49%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6035	60.35%
Acute Oral Toxicity (c)	II	0.7203	72.03%
Estrogen receptor binding	-	0.7003	70.03%
Androgen receptor binding	-	0.8899	88.99%
Thyroid receptor binding	-	0.6583	65.83%
Glucocorticoid receptor binding	-	0.7799	77.99%
Aromatase binding	-	0.6696	66.96%
PPAR gamma	-	0.8290	82.90%
Honey bee toxicity	-	0.9426	94.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.8350	83.50%

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	92.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.41%	91.11%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	85.96%	97.88%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2227
• LOTUS: LTS0074604
• wikiData: Q27074499