[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-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: d5b14bed-d50b-4d9d-95a3-d0130a2fec2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]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): CC=C(C)C(=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)O)C)OC(=O)C6=CC=CC=C6)O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)NC(C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)O)C)OC(=O)C6=CC=CC=C6)O)O
• InChI: InChI=1S/C43H51NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31-34,36,46-48,53H,19-21H2,1-7H3,(H,44,50)/b22-8+/t27-,28+,29+,31?,32+,33+,34-,36-,41+,42-,43+/m0/s1
• InChI Key: ADDGUHVEJPNWQZ-VGNPSGPUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₁NO₁₃
• Molecular Weight: 789.90 g/mol
• Exact Mass: 789.33604068 g/mol
• Topological Polar Surface Area (TPSA): 215.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9470	94.70%
Caco-2	-	0.8880	88.80%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6557	65.57%
OATP2B1 inhibitior	+	0.5162	51.62%
OATP1B1 inhibitior	-	0.4573	45.73%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8500	85.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9723	97.23%
P-glycoprotein inhibitior	+	0.7918	79.18%
P-glycoprotein substrate	+	0.9014	90.14%
CYP3A4 substrate	+	0.7652	76.52%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8889	88.89%
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	+	0.9365	93.65%
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	-	0.9149	91.49%
Skin irritation	-	0.7657	76.57%
Skin corrosion	-	0.9352	93.52%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7280	72.80%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.7020	70.20%
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	+	0.4641	46.41%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.8237	82.37%
Androgen receptor binding	+	0.8509	85.09%
Thyroid receptor binding	+	0.7575	75.75%
Glucocorticoid receptor binding	+	0.7821	78.21%
Aromatase binding	+	0.6214	62.14%
PPAR gamma	+	0.7866	78.66%
Honey bee toxicity	-	0.5901	59.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	28.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.85%	90.17%
CHEMBL2581	P07339	Cathepsin D	98.72%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.24%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.67%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	95.93%	87.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.75%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.48%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.52%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.48%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.60%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.39%	94.62%
CHEMBL5028	O14672	ADAM10	91.20%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.68%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.64%	83.00%
CHEMBL340	P08684	Cytochrome P450 3A4	90.24%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.09%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.59%	91.49%
CHEMBL2535	P11166	Glucose transporter	89.28%	98.75%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.58%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.57%	96.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.46%	96.47%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.94%	89.44%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.21%	94.08%
CHEMBL4302	P08183	P-glycoprotein 1	82.67%	92.98%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.49%	97.09%
CHEMBL4208	P20618	Proteasome component C5	81.95%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.86%	97.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.79%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.41%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.35%	100.00%

Plants that contains it

• Taxus baccata
• Taxus wallichiana

Cross-Links

• PubChem: 10197303
• NPASS: NPC49524