10-Deacetyltaxol

Details

• Internal ID: a3a37371-7992-4e5c-8d1f-2e03722b5936
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-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)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)O
• 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)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)O
• InChI: InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
• InChI Key: TYLVGQKNNUHXIP-MHHARFCSSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₄₉NO₁₃
• Molecular Weight: 811.90 g/mol
• Exact Mass: 811.32039062 g/mol
• Topological Polar Surface Area (TPSA): 215.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• DEACETYLTAXOL
• 78432-77-6
• 10-Desacetyl Paclitaxel
• 10-Deacetylpaclitaxel
• 10-deacetyl-paclitaxel
• UNII-B77R96LJLK
• B77R96LJLK
• Deacetyltaxol10-Deacetyltaxol
• 7-EPI-10-DEACETYL-TAXOL
• 10-Deacetyl-7-epitaxol
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 10-deacetyl taxol
• 10-Deacetyl-7-epi-taxol
• 10-Desacetylpaclitaxel
• 111149-94-1
• 10-Desacetyltaxol
• Deacetyl Paclitaxel
• Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphar*,betas*),11alpha,12alpha,12aalpha,12balpha))-
• Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha]]-
• BKR
• 10-Deacetyltaxol A
• 10-Deacetyl Paclitaxel
• 10-O-deacetylpaclitaxel
• 7-epi-10-deacetyltaxol; 10-Deacetyl-7-epipaclitaxel
• 7-epi-10-deacetyl taxol
• 10-DAT
• CHEMBL302324
• SCHEMBL13043169
• DTXSID00999763
• TYLVGQKNNUHXIP-MHHARFCSSA-N
• HY-N1391
• MFCD01075780
• s3933
• AKOS030242787
• CCG-270505
• AS-57909
• PD088403
• PACLITAXEL IMPURITY G [EP IMPURITY]
• CS-0016811
• Q27274453
• 4-(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1,7beta,10beta-trihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate
• N-(3-{[4-(Acetyloxy)-2-(benzoyloxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy}-2-hydroxy-3-oxo-1-phenylpropyl)benzenecarboximidic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9470	94.70%
Caco-2	-	0.9141	91.41%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6557	65.57%
OATP2B1 inhibitior	+	0.5762	57.62%
OATP1B1 inhibitior	-	0.5983	59.83%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8700	87.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9717	97.17%
P-glycoprotein inhibitior	+	0.7826	78.26%
P-glycoprotein substrate	+	0.9267	92.67%
CYP3A4 substrate	+	0.7807	78.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
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	+	0.9613	96.13%
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	-	0.9122	91.22%
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	+	0.7791	77.91%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.7395	73.95%
skin sensitisation	-	0.8230	82.30%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6086	60.86%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.8521	85.21%
Thyroid receptor binding	+	0.7387	73.87%
Glucocorticoid receptor binding	+	0.7638	76.38%
Aromatase binding	+	0.5964	59.64%
PPAR gamma	+	0.7908	79.08%
Honey bee toxicity	-	0.6304	63.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
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	251.2 nM; 25.1 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.78%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.33%	85.14%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	98.53%	87.67%
CHEMBL2581	P07339	Cathepsin D	98.23%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.20%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.20%	91.49%
CHEMBL5028	O14672	ADAM10	91.34%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.12%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.45%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.22%	96.47%
CHEMBL2535	P11166	Glucose transporter	89.71%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	89.54%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.22%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.02%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.17%	97.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.82%	83.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.97%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.56%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.75%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.85%	94.08%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.06%	89.44%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.87%	97.09%
CHEMBL4208	P20618	Proteasome component C5	81.23%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.77%	100.00%

Plants that contains it

• Corylus avellana
• Taxus baccata
• Taxus brevifolia
• Taxus canadensis
• Taxus cuspidata
• Taxus mairei
• Taxus wallichiana
• Taxus wallichiana var. chinensis

Cross-Links

• PubChem: 155831
• NPASS: NPC242662
• ChEMBL: CHEMBL302324
• LOTUS: LTS0212352
• wikiData: Q27274453