(2aR-(2aalpha,4beta,4abeta,5alpha,6beta,9alpha,11beta,12alpha,12aalpha,12balpha))-3,4,4a,5,6,9,10,11,12,12a-Decahydro-4a,8,13,13-tetramethyl-7,14-methano-1H-cyclodeca(3,4)benz(1,2-b)oxete-4,5,6,9,12,12b(2aH)-hexol 4,5,6,9,12b-pentaacetate 12-benzoate

Details

• Internal ID: 94635820-366f-4def-b025-cb0641ff41b4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1R,2R,3R,4S,7R,9S,10S,11R,12R,15S)-4,9,11,12,15-pentaacetyloxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• SMILES (Canonical): CC1=C2C(C(C3(C(CC4C(C3C(C(C2(C)C)CC1OC(=O)C)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)OC(=O)C)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC1=C2[C@H]([C@@H]([C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@H](C2(C)C)C[C@@H]1OC(=O)C)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)OC(=O)C)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C37H46O13/c1-18-26(45-19(2)38)15-25-30(49-34(43)24-13-11-10-12-14-24)32-36(9,27(46-20(3)39)16-28-37(32,17-44-28)50-23(6)42)33(48-22(5)41)31(47-21(4)40)29(18)35(25,7)8/h10-14,25-28,30-33H,15-17H2,1-9H3/t25-,26-,27-,28+,30+,31+,32-,33-,36+,37-/m0/s1
• InChI Key: JHPBZGSKESVROC-IGIVFXLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₆O₁₃
• Molecular Weight: 698.80 g/mol
• Exact Mass: 698.29384152 g/mol
• Topological Polar Surface Area (TPSA): 167.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 13
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 1-dehydroxy-baccatin VI
• DTXSID80925000
• (2aR-(2aalpha,4beta,4abeta,5alpha,6beta,9alpha,11beta,12alpha,12aalpha,12balpha))-3,4,4a,5,6,9,10,11,12,12a-Decahydro-4a,8,13,13-tetramethyl-7,14-methano-1H-cyclodeca(3,4)benz(1,2-b)oxete-4,5,6,9,12,12b(2aH)-hexol 4,5,6,9,12b-pentaacetate 12-benzoate
• 4,7,9,10,13-Pentakis(acetyloxy)-5,20-epoxytax-11-en-2-yl benzoate
• [(1R,2R,3R,4S,7R,9S,10S,11R,12R,15S)-4,9,11,12,15-Pentaacetyloxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 7,14-Methano-1H-cyclodeca(3,4)benz(1,2-b)oxete-4,5,6,9,12,12b(2aH)-hexol, 3,4,4a,5,6,9,10,11,12,12a-decahydro-4a,8,13,13-tetramethyl-, 4,5,6,9,12b-pentaacetate 12-benzoate, (2aR-(2aalpha,4beta,4abeta,5alpha,6beta,9alpha,11beta,12alpha,12aalpha,12balpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	-	0.7563	75.63%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7951	79.51%
OATP2B1 inhibitior	-	0.7148	71.48%
OATP1B1 inhibitior	+	0.8067	80.67%
OATP1B3 inhibitior	+	0.9049	90.49%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9842	98.42%
P-glycoprotein inhibitior	+	0.9152	91.52%
P-glycoprotein substrate	+	0.6538	65.38%
CYP3A4 substrate	+	0.6958	69.58%
CYP2C9 substrate	-	0.8123	81.23%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	-	0.6533	65.33%
CYP2C9 inhibition	-	0.7096	70.96%
CYP2C19 inhibition	-	0.6495	64.95%
CYP2D6 inhibition	-	0.8947	89.47%
CYP1A2 inhibition	-	0.5629	56.29%
CYP2C8 inhibition	+	0.8993	89.93%
CYP inhibitory promiscuity	-	0.6976	69.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4558	45.58%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.8852	88.52%
Skin irritation	-	0.7068	70.68%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7358	73.58%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5263	52.63%
skin sensitisation	-	0.6703	67.03%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5655	56.55%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.8156	81.56%
Androgen receptor binding	+	0.7150	71.50%
Thyroid receptor binding	+	0.6148	61.48%
Glucocorticoid receptor binding	+	0.7980	79.80%
Aromatase binding	+	0.6772	67.72%
PPAR gamma	+	0.7653	76.53%
Honey bee toxicity	-	0.6437	64.37%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6245	62.45%
Fish aquatic toxicity	+	0.9958	99.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.17%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.83%	96.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	95.89%	81.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.74%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.92%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	92.05%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.66%	95.50%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	91.00%	87.67%
CHEMBL1951	P21397	Monoamine oxidase A	90.49%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.02%	99.23%
CHEMBL5028	O14672	ADAM10	88.98%	97.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	88.95%	89.44%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	86.46%	83.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.98%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.92%	94.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.78%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.37%	90.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.77%	97.14%
CHEMBL4208	P20618	Proteasome component C5	81.63%	90.00%

Plants that contains it

• Taxus cuspidata
• Taxus mairei
• Taxus wallichiana var. chinensis

Cross-Links

• PubChem: 3081235
• LOTUS: LTS0250732
• wikiData: Q82899232