Thiarubrine A

Details

• Internal ID: 35a88082-26d3-4a18-b4bd-0ed8173fa6c9
• Taxonomy: Organoheterocyclic compounds > Dithiins
• IUPAC Name: 3-hex-5-en-1,3-diynyl-6-prop-1-ynyldithiine
• SMILES (Canonical): CC#CC1=CC=C(SS1)C#CC#CC=C
• SMILES (Isomeric): CC#CC1=CC=C(SS1)C#CC#CC=C
• InChI: InChI=1S/C13H8S2/c1-3-5-6-7-9-13-11-10-12(8-4-2)14-15-13/h3,10-11H,1H2,2H3
• InChI Key: XZHCLKKXXPKULI-UHFFFAOYSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈S₂
• Molecular Weight: 228.30 g/mol
• Exact Mass: 228.00674260 g/mol
• Topological Polar Surface Area (TPSA): 50.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.37
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• thiarubrin a
• Thiarubrin(e) A
• 63543-09-9
• 3-(5-Hexene-1,3-diynyl)-6-(1-propynyl)-1,2-dithiin
• 1,2-Dithiin, 3-(5-hexene-1,3-diynyl)-6-(1-propynyl)-
• UNII-DVV5W0EG1Z
• DVV5W0EG1Z
• 3-(hexa-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiine
• 3-hex-5-en-1,3-diynyl-6-prop-1-ynyl-dithiine
• 1-(2-Methyleth-1-yn)-4-(hex-1,3-diyn-5-ene)-2,3-dithiacyclohex-1,3-diene
• Thiorubrine A
• 3-hex-5-en-1,3-diynyl-6-prop-1-ynyldithiine
• THIARUBRINE A [MI]
• CHEBI:9538
• SCHEMBL1653142
• C13H8S2
• DTXSID80212947
• C13-H8-S2
• LMFA12000371
• C08461
• Q27108431
• 1,2-DITHIIN, 3-(5-HEXENE-1,3-DIYN-1-YL)-6-(1-PROPYN-1-YL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.5124	51.24%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3971	39.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8917	89.17%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9138	91.38%
P-glycoprotein inhibitior	-	0.9560	95.60%
P-glycoprotein substrate	-	0.9434	94.34%
CYP3A4 substrate	-	0.6266	62.66%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8271	82.71%
CYP3A4 inhibition	-	0.5475	54.75%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.5141	51.41%
CYP2D6 inhibition	-	0.8224	82.24%
CYP1A2 inhibition	+	0.5598	55.98%
CYP2C8 inhibition	-	0.8075	80.75%
CYP inhibitory promiscuity	+	0.7427	74.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5919	59.19%
Carcinogenicity (trinary)	Non-required	0.5633	56.33%
Eye corrosion	-	0.5547	55.47%
Eye irritation	-	0.5631	56.31%
Skin irritation	+	0.6005	60.05%
Skin corrosion	-	0.6599	65.99%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7226	72.26%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.7053	70.53%
skin sensitisation	+	0.6178	61.78%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.4770	47.70%
Acute Oral Toxicity (c)	III	0.4604	46.04%
Estrogen receptor binding	-	0.4863	48.63%
Androgen receptor binding	-	0.6593	65.93%
Thyroid receptor binding	+	0.5889	58.89%
Glucocorticoid receptor binding	+	0.7136	71.36%
Aromatase binding	+	0.7786	77.86%
PPAR gamma	+	0.7363	73.63%
Honey bee toxicity	-	0.8493	84.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9595	95.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.03%	83.57%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.04%	96.09%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	85.95%	96.42%
CHEMBL2487	P05067	Beta amyloid A4 protein	84.36%	96.74%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.45%	80.96%
CHEMBL3401	O75469	Pregnane X receptor	82.74%	94.73%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.56%	85.30%
CHEMBL2581	P07339	Cathepsin D	80.88%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.19%	89.34%

Plants that contains it

• Ambrosia artemisiifolia
• Ambrosia chamissonis
• Ambrosia trifida
• Aspilia pluriseta
• Chaenactis douglasii
• Eriophyllum lanatum
• Phragmites australis
• Picradeniopsis multiflora
• Trigonella foenum-graecum
• Wedelia hookeriana

Cross-Links

• PubChem: 72386
• NPASS: NPC312416
• LOTUS: LTS0123497
• wikiData: Q27108431