Baccatin Iii

Details

• Internal ID: d9d1b263-fe02-4ee0-964d-3a171905463f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• InChI: InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
• InChI Key: OVMSOCFBDVBLFW-VHLOTGQHSA-N
• Popularity: 305 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₁
• Molecular Weight: 586.60 g/mol
• Exact Mass: 586.24141202 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 27548-93-2
• CHEBI:32898
• 40K5PZ0K67
• 7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-
• DTXSID301029474
• NSC-330753
• 7,11-METHANO-5H-CYCLODECA(3,4)BENZ(1,2-B)OXET-5-ONE, 6,12B-BIS(ACETYLOXY)-12-(BENZOYLOXY)-1,2A,3,4,4A,6,9,10,11,12,12A,12B-DODECAHYDRO-4,9,11-TRIHYDROXY-4A,8,13,13-TETRAMETHYL-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-
• ((1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo(11.3.1.03,10.04,7)heptadec-13-en-2-yl) benzoate
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• RefChem:116207
• DTXCID501514724
• 636-675-9
• NSC330753
• BACCATINE III
• MFCD00153921
• C31H38O11
• Paclitaxel EP Impurity N
• [(1~{S},2~{S},3~{R},4~{S},7~{R},9~{S},10~{S},12~{R},15~{S})-4,12-diacetyloxy-10,14,16,16-tetramethyl-1,9,15-tris(oxidanyl)-11-oxidanylidene-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl] benzoate
• NSC 330753
• UNII-40K5PZ0K67
• 13-O-De[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]paclitaxel (Baccatin III)
• Baccatin III?
• Baccatin III (Standard)
• BACCATIN III [WHO-DD]
• CHEMBL288043
• SCHEMBL3118475
• HY-N6985R
• EX-A832
• OVMSOCFBDVBLFW-VHLOTGQHSA-N
• Baccatin III, >=95% (HPLC)
• HY-N6985
• AKOS024462641
• CCG-208344
• FB18122
• (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one
• 7,11-Methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha,11alpha,12alpha,12aalpha,12balpha))-
• AS-35071
• PACLITAXEL IMPURITY N [EP IMPURITY]
• CS-0013149
• NS00093867
• 548B932
• F600860
• Q15410249
• Baccatin III; O-De[(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoyl]paclitaxel
• (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(Benzoyloxy)-4,9,11-trihydroxy-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]oxete-6,12b-diyl diacetate
• (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate
• (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihyd roxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one;NSC 330753
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetoxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• [2aR-(2aalpha,4beta,4abeta,6beta,9alpha,11alpha,12alpha,12aalpha,12balpha)]-6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one
• 4,10beta-bis(acetyloxy)-1,7beta,13alpha-trihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate (13-O-de[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]paclitaxel
• 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate
• R3Q

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.7624	76.24%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.6920	69.20%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8166	81.66%
P-glycoprotein inhibitior	+	0.7974	79.74%
P-glycoprotein substrate	+	0.8348	83.48%
CYP3A4 substrate	+	0.7359	73.59%
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	+	0.8973	89.73%
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	-	0.9006	90.06%
Skin irritation	-	0.6618	66.18%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7040	70.40%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6504	65.04%
skin sensitisation	-	0.7239	72.39%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6890	68.90%
Acute Oral Toxicity (c)	III	0.6075	60.75%
Estrogen receptor binding	+	0.8051	80.51%
Androgen receptor binding	+	0.7665	76.65%
Thyroid receptor binding	+	0.5917	59.17%
Glucocorticoid receptor binding	+	0.7344	73.44%
Aromatase binding	+	0.6558	65.58%
PPAR gamma	+	0.6997	69.97%
Honey bee toxicity	-	0.6985	69.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
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
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.84%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	96.77%	90.17%
CHEMBL2581	P07339	Cathepsin D	96.54%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	94.62%	81.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	94.17%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.40%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.19%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.25%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.49%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.66%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.15%	94.62%
CHEMBL5028	O14672	ADAM10	88.91%	97.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.11%	83.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.42%	99.23%
CHEMBL4208	P20618	Proteasome component C5	85.94%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.51%	91.19%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	85.49%	89.44%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.51%	92.67%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.48%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.28%	97.14%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.24%	90.24%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.22%	94.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.79%	89.00%

Plants that contains it

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

Cross-Links

• PubChem: 65366
• NPASS: NPC114357
• ChEMBL: CHEMBL288043
• LOTUS: LTS0248764
• wikiData: Q15410249