10-deacetylbaccatin III

Details

• Internal ID: 6fb5ebfa-ea10-4a06-96d9-e580ffe2c065
• 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-1,9,12,15-tetrahydroxy-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)(CC1O)O)OC(=O)C5=CC=CC=C5)(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]1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O
• InChI: InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1
• InChI Key: YWLXLRUDGLRYDR-ZHPRIASZSA-N
• Popularity: 448 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₀
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.23084734 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 32981-86-5
• 10-Deacetylbaccatine III
• UNII-4K6EWW2Z45
• CHEBI:18193
• 10-DB III
• 10-DEACETYL-BACCATIN III
• 10.BETA.-DEACETYLBACCATIN III
• NSC 251677
• NSC-251677
• 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 7,11-METHANO-5H-CYCLODECA(3,4)BENZ(1,2-B)OXET-5-ONE, 12B-(ACETYLOXY)-12-(BENZOYLOXY)-1,2A,3,4,4A,6,9,10,11,12,12A,12B-DODECAHYDRO-4,6,9,11-TETRAHYDROXY-4A,8,13,13-TETRAMETHYL-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)
• ((1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo(11.3.1.03,10.04,7)heptadec-13-en-2-yl) benzoate
• 4-(Acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo(11.3.1.0,.0,)heptadec-13-en-2-yl benzoic acid
• 4-(Acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0,.0,]heptadec-13-en-2-yl benzoic acid
• RefChem:77459
• 10-Deacetyl-baccatine III
• 10BETA-DEACETYLBACCATIN III
• 7,11-Methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR-(2aalpha,4beta,4aalpha,6beta,9alpha,11alpha,12alpha,12aalpha,12balpha))-
• 10-Deacetylbaccatin
• 10-Deacetyl baccatin III
• MFCD09027979
• 4K6EWW2Z45
• 10-O-Deacetylbaccatin III
• 10-DAB (10-Deacetylbaccatin)
• C29H36O10
• Docetaxel EP Impurity E
• 10-DEACETYLBACCATIN-III
• zoate
• 10-DeacetylbaccatinIII
• 10-deactyl baccatin III
• 10-Deacetyl baccatine III
• SCHEMBL33495
• MLS006011993
• Baccatin III, 10-Deacetyl-
• CHEMBL393912
• orb1306138
• DTXSID80865659
• YWLXLRUDGLRYDR-ZHPRIASZSA-N
• (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
• EX-A3597
• 10-Deacetylbaccatin III (Standard)
• HY-16565R
• s2409
• AKOS025401509
• CCG-269977
• FD11737
• 7,11-Methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-
• AC-20218
• HY-16565
• PD012455
• SMR004703546
• D4148
• NS00015516
• F12951
• AB01566852_01
• F787564
• Q163856
• BRD-K96631475-001-02-4
• BRD-K96631475-001-04-0
• 10-Deacetylbaccatin III from Taxus baccata, >=95% (HPLC)
• (2AR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methan
• (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1h-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl ben
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetoxy-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.7330	73.30%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.7666	76.66%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6905	69.05%
P-glycoprotein inhibitior	+	0.7397	73.97%
P-glycoprotein substrate	+	0.7922	79.22%
CYP3A4 substrate	+	0.7239	72.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.7624	76.24%
CYP2C19 inhibition	-	0.8309	83.09%
CYP2D6 inhibition	-	0.8764	87.64%
CYP1A2 inhibition	-	0.7292	72.92%
CYP2C8 inhibition	+	0.8588	85.88%
CYP inhibitory promiscuity	-	0.8651	86.51%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4468	44.68%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.6618	66.18%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7759	77.59%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6453	64.53%
skin sensitisation	-	0.7239	72.39%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6870	68.70%
Acute Oral Toxicity (c)	III	0.6075	60.75%
Estrogen receptor binding	+	0.7746	77.46%
Androgen receptor binding	+	0.7646	76.46%
Thyroid receptor binding	+	0.5395	53.95%
Glucocorticoid receptor binding	+	0.6824	68.24%
Aromatase binding	+	0.6625	66.25%
PPAR gamma	+	0.5945	59.45%
Honey bee toxicity	-	0.7027	70.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.46%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.14%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.67%	81.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.35%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.89%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.40%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.11%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.92%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	90.84%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL5028	O14672	ADAM10	90.03%	97.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.82%	83.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.67%	89.44%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.55%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.31%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.75%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.60%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.19%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.91%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.73%	89.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.34%	94.08%

Plants that contains it

• Corylus avellana
• Taxus baccata
• Taxus brevifolia
• Taxus canadensis
• Taxus chinensis
• Taxus cuspidata
• Taxus floridana
• Taxus mairei
• Taxus sumatrana
• Taxus wallichiana

Cross-Links

• PubChem: 154272
• NPASS: NPC134685
• ChEMBL: CHEMBL393912
• LOTUS: LTS0231236
• wikiData: Q163856