Paclitaxel IMpurity O

Details

• Internal ID: e48ac159-7867-4c34-be65-7d01d3dfedac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-phenyl-3-[[(E)-3-phenylprop-2-enoyl]amino]propanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• SMILES (Canonical): CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C=CC6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• SMILES (Isomeric): CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)/C=C/C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• InChI: InChI=1S/C49H53NO14/c1-27-33(62-45(58)39(55)38(31-18-12-8-13-19-31)50-36(54)23-22-30-16-10-7-11-17-30)25-49(59)43(63-44(57)32-20-14-9-15-21-32)41-47(6,34(53)24-35-48(41,26-60-35)64-29(3)52)42(56)40(61-28(2)51)37(27)46(49,4)5/h7-23,33-35,38-41,43,53,55,59H,24-26H2,1-6H3,(H,50,54)/b23-22+/t33-,34-,35+,38-,39+,40+,41-,43-,47+,48-,49+/m0/s1
• InChI Key: SESDEFPIFUOEIX-UFWAFWIVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₅₃NO₁₄
• Molecular Weight: 879.90 g/mol
• Exact Mass: 879.34660536 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 4.14
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• 219783-77-4
• CHEMBL500509
• (2R,3S)-2-Hydroxy-3-(styrylcarbonylamino)-3-phenylpropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-5beta,20-epoxy-9-oxotax-11-en-13alpha-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9470	94.70%
Caco-2	-	0.9081	90.81%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6557	65.57%
OATP2B1 inhibitior	+	0.5927	59.27%
OATP1B1 inhibitior	-	0.5549	55.49%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9246	92.46%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9741	97.41%
P-glycoprotein inhibitior	+	0.7793	77.93%
P-glycoprotein substrate	+	0.9286	92.86%
CYP3A4 substrate	+	0.7752	77.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.9647	96.47%
CYP inhibitory promiscuity	-	0.8937	89.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4813	48.13%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9085	90.85%
Skin irritation	-	0.7657	76.57%
Skin corrosion	-	0.9352	93.52%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7568	75.68%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5370	53.70%
skin sensitisation	-	0.8230	82.30%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.5682	56.82%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.8174	81.74%
Androgen receptor binding	+	0.8320	83.20%
Thyroid receptor binding	+	0.7235	72.35%
Glucocorticoid receptor binding	+	0.7586	75.86%
Aromatase binding	+	0.5893	58.93%
PPAR gamma	+	0.8073	80.73%
Honey bee toxicity	-	0.6089	60.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.88%	90.17%
CHEMBL2581	P07339	Cathepsin D	98.18%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.23%	85.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	97.05%	81.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.74%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.90%	96.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	95.59%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.28%	95.56%
CHEMBL4302	P08183	P-glycoprotein 1	93.80%	92.98%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.76%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.53%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.53%	91.49%
CHEMBL5028	O14672	ADAM10	92.26%	97.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.43%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.16%	83.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.01%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.27%	99.23%
CHEMBL3524	P56524	Histone deacetylase 4	90.26%	92.97%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	88.21%	89.44%
CHEMBL4267	P37173	TGF-beta receptor type II	87.97%	88.18%
CHEMBL2535	P11166	Glucose transporter	87.76%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	87.69%	91.19%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.20%	89.34%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.96%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.64%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.99%	94.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.52%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.97%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.89%	85.31%
CHEMBL4208	P20618	Proteasome component C5	83.46%	90.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.19%	94.08%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.81%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.53%	97.14%

Plants that contains it

• Taxus baccata

Cross-Links

• PubChem: 10373467
• NPASS: NPC22933