Thailanstatin C

Details

• Internal ID: 52057ebf-03b0-488c-ab45-9dcf4e5871e6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > C-glycosyl compounds
• IUPAC Name: 2-[(2S,4S,5R,6R)-4-(chloromethyl)-6-[(1E,3E)-5-[(2S,3S,5R,6R)-3,6-dimethyl-5-[[(Z,4S)-4-(2-methylpropanoyloxy)pent-2-enoyl]amino]oxan-2-yl]-3-methylpenta-1,3-dienyl]-4,5-dihydroxyoxan-2-yl]acetic acid
• SMILES (Canonical): CC1CC(C(OC1CC=C(C)C=CC2C(C(CC(O2)CC(=O)O)(CCl)O)O)C)NC(=O)C=CC(C)OC(=O)C(C)C
• SMILES (Isomeric): C[C@H]1C[C@H]([C@H](O[C@H]1C/C=C(\C)/C=C/[C@@H]2[C@H]([C@@](C[C@H](O2)CC(=O)O)(CCl)O)O)C)NC(=O)/C=C\[C@H](C)OC(=O)C(C)C
• InChI: InChI=1S/C30H46ClNO9/c1-17(2)29(37)39-20(5)9-12-26(33)32-23-13-19(4)24(40-21(23)6)10-7-18(3)8-11-25-28(36)30(38,16-31)15-22(41-25)14-27(34)35/h7-9,11-12,17,19-25,28,36,38H,10,13-16H2,1-6H3,(H,32,33)(H,34,35)/b11-8+,12-9-,18-7+/t19-,20-,21+,22+,23+,24-,25+,28+,30+/m0/s1
• InChI Key: IUEAQIHFZAHMMU-WEDQMBCXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆ClNO₉
• Molecular Weight: 600.10 g/mol
• Exact Mass: 599.2861097 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

• 1426953-24-3
• CHEMBL2331577
• EX-A5054
• AKOS040756787
• HY-139103
• CS-0179602

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8170	81.70%
Caco-2	-	0.8246	82.46%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6274	62.74%
OATP2B1 inhibitior	-	0.7219	72.19%
OATP1B1 inhibitior	+	0.8563	85.63%
OATP1B3 inhibitior	+	0.9163	91.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6208	62.08%
P-glycoprotein inhibitior	+	0.6838	68.38%
P-glycoprotein substrate	+	0.6451	64.51%
CYP3A4 substrate	+	0.7110	71.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8892	88.92%
CYP3A4 inhibition	-	0.8244	82.44%
CYP2C9 inhibition	-	0.8533	85.33%
CYP2C19 inhibition	-	0.8073	80.73%
CYP2D6 inhibition	-	0.9224	92.24%
CYP1A2 inhibition	-	0.9036	90.36%
CYP2C8 inhibition	+	0.6562	65.62%
CYP inhibitory promiscuity	-	0.8497	84.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8238	82.38%
Carcinogenicity (trinary)	Non-required	0.5224	52.24%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9360	93.60%
Skin irritation	-	0.7304	73.04%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	+	0.5630	56.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.4766	47.66%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5823	58.23%
skin sensitisation	-	0.8360	83.60%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5441	54.41%
Acute Oral Toxicity (c)	III	0.6039	60.39%
Estrogen receptor binding	+	0.6699	66.99%
Androgen receptor binding	+	0.6347	63.47%
Thyroid receptor binding	+	0.5154	51.54%
Glucocorticoid receptor binding	+	0.6983	69.83%
Aromatase binding	+	0.5924	59.24%
PPAR gamma	+	0.6359	63.59%
Honey bee toxicity	-	0.6792	67.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9764	97.64%

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	98.87%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.77%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	94.33%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.32%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	89.73%	89.50%
CHEMBL3401	O75469	Pregnane X receptor	89.68%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.36%	96.77%
CHEMBL3776	Q14790	Caspase-8	89.20%	97.06%
CHEMBL5028	O14672	ADAM10	88.00%	97.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.36%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	86.90%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.27%	97.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.42%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.72%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.85%	96.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.09%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.69%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.54%	95.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.53%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.26%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.12%	97.09%
CHEMBL5957	P21589	5'-nucleotidase	80.70%	97.78%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.60%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.50%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71665770
• LOTUS: LTS0001026
• wikiData: Q105120509