Dysidenin

Details

• Internal ID: fbdfbd1d-9390-4c1a-ad61-cadbb6bcdda9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: (2S,4S)-5,5,5-trichloro-4-methyl-2-[methyl-[(3S)-4,4,4-trichloro-3-methylbutanoyl]amino]-N-[(1S)-1-(1,3-thiazol-2-yl)ethyl]pentanamide
• SMILES (Canonical): CC(CC(C(=O)NC(C)C1=NC=CS1)N(C)C(=O)CC(C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
• SMILES (Isomeric): C[C@@H](C[C@@H](C(=O)N[C@@H](C)C1=NC=CS1)N(C)C(=O)C[C@H](C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
• InChI: InChI=1S/C17H23Cl6N3O2S/c1-9(16(18,19)20)7-12(14(28)25-11(3)15-24-5-6-29-15)26(4)13(27)8-10(2)17(21,22)23/h5-6,9-12H,7-8H2,1-4H3,(H,25,28)/t9-,10-,11-,12-/m0/s1
• InChI Key: BFVRAKVNXYQMID-BJDJZHNGSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃Cl₆N₃O₂S
• Molecular Weight: 546.20 g/mol
• Exact Mass: 544.961264 g/mol
• Topological Polar Surface Area (TPSA): 90.50 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.94
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• CHEMBL391079
• D08WDW
• CHEBI:189706
• BDBM50221405
• Q21099603
• (2S,4S)-5,5,5-trichloro-4-methyl-2-[methyl-[(3S)-4,4,4-trichloro-3-methylbutanoyl]amino]-N-[(1S)-1-(1,3-thiazol-2-yl)ethyl]pentanamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9814	98.14%
Caco-2	-	0.7014	70.14%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4337	43.37%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5765	57.65%
P-glycoprotein inhibitior	-	0.6318	63.18%
P-glycoprotein substrate	-	0.5058	50.58%
CYP3A4 substrate	+	0.5826	58.26%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8476	84.76%
CYP3A4 inhibition	+	0.5379	53.79%
CYP2C9 inhibition	-	0.6808	68.08%
CYP2C19 inhibition	+	0.5449	54.49%
CYP2D6 inhibition	-	0.9021	90.21%
CYP1A2 inhibition	-	0.7090	70.90%
CYP2C8 inhibition	-	0.8581	85.81%
CYP inhibitory promiscuity	-	0.5637	56.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7518	75.18%
Carcinogenicity (trinary)	Non-required	0.6205	62.05%
Eye corrosion	-	0.9732	97.32%
Eye irritation	-	0.9726	97.26%
Skin irritation	-	0.7312	73.12%
Skin corrosion	-	0.8766	87.66%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6882	68.82%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5686	56.86%
Acute Oral Toxicity (c)	III	0.5526	55.26%
Estrogen receptor binding	-	0.5075	50.75%
Androgen receptor binding	+	0.6269	62.69%
Thyroid receptor binding	+	0.6722	67.22%
Glucocorticoid receptor binding	+	0.6248	62.48%
Aromatase binding	-	0.5293	52.93%
PPAR gamma	+	0.5231	52.31%
Honey bee toxicity	-	0.8650	86.50%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6052	60.52%
Fish aquatic toxicity	+	0.7115	71.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	9000 nM	Ki	PMID: 17826100
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	8000 nM	Ki	PMID: 17826100

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	97.12%	89.34%
CHEMBL2581	P07339	Cathepsin D	96.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.48%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	96.41%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	92.90%	96.90%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	92.70%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.54%	93.10%
CHEMBL2094135	Q96BI3	Gamma-secretase	92.37%	98.05%
CHEMBL4208	P20618	Proteasome component C5	90.82%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.64%	99.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.44%	100.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.10%	92.29%
CHEMBL3308	P55212	Caspase-6	82.97%	97.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.94%	90.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.85%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.53%	90.71%

Plants that contains it

• Achillea leptophylla
• Aldama cordifolia
• Cordiera macrophylla
• Dioscorea futschauensis
• Dorstenia barnimiana
• Petrosedum forsterianum
• Rubia yunnanensis
• Uvaria mocoli
• Verbascum georgicum
• Zieria chevalieri

Cross-Links

• PubChem: 10007601
• NPASS: NPC137705
• ChEMBL: CHEMBL391079
• LOTUS: LTS0257881
• wikiData: Q21099603