5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene

Details

• Internal ID: 6515d0a3-762c-4e4a-b947-244df28ec4ae
• Taxonomy: Organoheterocyclic compounds > Bi- and oligothiophenes
• IUPAC Name: 1-chloro-4-(5-thiophen-2-ylthiophen-2-yl)but-3-yn-2-ol
• SMILES (Canonical): C1=CSC(=C1)C2=CC=C(S2)C#CC(CCl)O
• SMILES (Isomeric): C1=CSC(=C1)C2=CC=C(S2)C#CC(CCl)O
• InChI: InChI=1S/C12H9ClOS2/c13-8-9(14)3-4-10-5-6-12(16-10)11-2-1-7-15-11/h1-2,5-7,9,14H,8H2
• InChI Key: GFYWABYZRGXGNU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₉ClOS₂
• Molecular Weight: 268.80 g/mol
• Exact Mass: 267.9783349 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• CHEBI:184939
• DTXSID901248824
• 4-[2,2'-Bithiophen]-5-yl-1-chloro-3-butyn-2-ol
• 5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene
• 4-{[2,2'-bithiophene]-5-yl}-1-chlorobut-3-yn-2-ol
• 1-chloro-4-(5-thiophen-2-ylthiophen-2-yl)but-3-yn-2-ol
• 1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol, 8CI
• 1020-03-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	-	0.5557	55.57%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7323	73.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9178	91.78%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8572	85.72%
P-glycoprotein inhibitior	-	0.9639	96.39%
P-glycoprotein substrate	-	0.9389	93.89%
CYP3A4 substrate	-	0.5631	56.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7553	75.53%
CYP3A4 inhibition	-	0.8578	85.78%
CYP2C9 inhibition	-	0.6210	62.10%
CYP2C19 inhibition	+	0.5700	57.00%
CYP2D6 inhibition	-	0.7911	79.11%
CYP1A2 inhibition	+	0.5933	59.33%
CYP2C8 inhibition	-	0.7032	70.32%
CYP inhibitory promiscuity	+	0.6339	63.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6217	62.17%
Carcinogenicity (trinary)	Danger	0.5305	53.05%
Eye corrosion	-	0.7711	77.11%
Eye irritation	-	0.8018	80.18%
Skin irritation	-	0.5400	54.00%
Skin corrosion	-	0.6007	60.07%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6783	67.83%
Micronuclear	-	0.6756	67.56%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.6009	60.09%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7729	77.29%
Acute Oral Toxicity (c)	II	0.6592	65.92%
Estrogen receptor binding	+	0.6652	66.52%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6174	61.74%
Glucocorticoid receptor binding	-	0.5254	52.54%
Aromatase binding	+	0.5208	52.08%
PPAR gamma	+	0.7691	76.91%
Honey bee toxicity	-	0.8643	86.43%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.6508	65.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.55%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.13%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.55%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.21%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.45%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.57%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.51%	95.93%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.23%	93.81%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.21%	94.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.03%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.28%	95.56%

Plants that contains it

• Pterocaulon virgatum

Cross-Links

• PubChem: 85528914
• LOTUS: LTS0000899
• wikiData: Q105007902