[(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Details

• Internal ID: 25d23906-fae2-4ef0-8ffe-526a83192cf9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• SMILES (Canonical): CCCCCC(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• SMILES (Isomeric): CCCCCC(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H](C4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• InChI: InChI=1S/C46H57NO14/c1-8-9-12-21-33(51)47-35(28-17-13-10-14-18-28)36(52)42(55)59-30-23-46(56)40(60-41(54)29-19-15-11-16-20-29)38-44(7,31(50)22-32-45(38,24-57-32)61-27(4)49)39(53)37(58-26(3)48)34(25(30)2)43(46,5)6/h10-11,13-20,30-32,35-38,40,50,52,56H,8-9,12,21-24H2,1-7H3,(H,47,51)/t30-,31-,32+,35-,36+,37+,38?,40-,44+,45-,46+/m0/s1
• InChI Key: BEHTXUBGUDGCNQ-QJUJXNPASA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₇NO₁₄
• Molecular Weight: 847.90 g/mol
• Exact Mass: 847.37790549 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 4.00
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 13

Synonyms

• CHEMBL1479301
• SCHEMBL15850511
• HMS2271F09
• SMR000578110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9566	95.66%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6291	62.91%
OATP2B1 inhibitior	-	0.6160	61.60%
OATP1B1 inhibitior	-	0.5609	56.09%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.8700	87.00%
OCT2 inhibitior	-	0.7776	77.76%
BSEP inhibitior	+	0.9762	97.62%
P-glycoprotein inhibitior	+	0.7864	78.64%
P-glycoprotein substrate	+	0.9439	94.39%
CYP3A4 substrate	+	0.7746	77.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	+	0.6018	60.18%
CYP2C9 inhibition	-	0.8098	80.98%
CYP2C19 inhibition	-	0.7766	77.66%
CYP2D6 inhibition	-	0.9011	90.11%
CYP1A2 inhibition	-	0.8297	82.97%
CYP2C8 inhibition	+	0.9593	95.93%
CYP inhibitory promiscuity	-	0.6155	61.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4776	47.76%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.7378	73.78%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7141	71.41%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.6390	63.90%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4749	47.49%
Acute Oral Toxicity (c)	III	0.6211	62.11%
Estrogen receptor binding	+	0.8526	85.26%
Androgen receptor binding	+	0.8257	82.57%
Thyroid receptor binding	+	0.6836	68.36%
Glucocorticoid receptor binding	+	0.7785	77.85%
Aromatase binding	+	0.6386	63.86%
PPAR gamma	+	0.8099	80.99%
Honey bee toxicity	-	0.6796	67.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9919	99.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	8912.5 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	35.5 nM; 35.5 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.90%	90.17%
CHEMBL2581	P07339	Cathepsin D	99.75%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.55%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.13%	95.17%
CHEMBL2996	Q05655	Protein kinase C delta	95.65%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.55%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.27%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.87%	96.47%
CHEMBL230	P35354	Cyclooxygenase-2	92.50%	89.63%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.77%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.34%	97.09%
CHEMBL2535	P11166	Glucose transporter	89.91%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.87%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.73%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.31%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.81%	94.45%
CHEMBL5028	O14672	ADAM10	88.72%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.66%	96.00%
CHEMBL299	P17252	Protein kinase C alpha	88.56%	98.03%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.49%	83.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.48%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	87.83%	91.49%
CHEMBL240	Q12809	HERG	86.14%	89.76%
CHEMBL4302	P08183	P-glycoprotein 1	85.63%	92.98%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.65%	89.00%
CHEMBL4267	P37173	TGF-beta receptor type II	84.42%	88.18%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.11%	81.11%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.13%	98.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.89%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.12%	94.08%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.80%	96.90%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.23%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.19%	93.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.11%	89.44%
CHEMBL5255	O00206	Toll-like receptor 4	80.31%	92.50%

Plants that contains it

• Taxus baccata
• Taxus cuspidata
• Taxus wallichiana

Cross-Links

• PubChem: 24791028
• NPASS: NPC306001
• ChEMBL: CHEMBL1479301