Epothilone B

Details

• Internal ID: 665dbd4b-75ca-4767-ba0e-4915448b9f6e
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Epothilones and analogues
• IUPAC Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• InChI: InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
• InChI Key: QXRSDHAAWVKZLJ-PVYNADRNSA-N
• Popularity: 768 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₁NO₆S
• Molecular Weight: 507.70 g/mol
• Exact Mass: 507.26545920 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Patupilone
• 152044-54-7
• (-)-Epothilone B
• Epo B
• Epothilon B
• EPO 906
• patupilona
• Epithilone b
• EPO 906A
• GNF-PF-193
• EPO-906
• patupilonum
• DTXSID4046862
• UEC0H0URSE
• EPO906A
• EPO-906A
• CHEBI:31550
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• DTXCID60819918
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• 4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE, 7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL)-, (1S,3S,7S,10R,11S,12S,16R)-
• (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-4,17-dioxabicyclo(14.1.0)heptadecane-5,9-dione
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo(14.1.0)heptadecane-5,9-dione
• RefChem:137329
• EPO906
• Patupilone (Epothilone B)
• Patupilone [INN]
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• MFCD02101921
• Epothilone B (synthetic)
• C27H41NO6S
• NCGC00181131-01
• 7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[1-METHYL-2-(2-METHYL-THIAZOL-4-YL)VINYL]-4,17-DIOXABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE
• Epothilone-B
• EpoB
• (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-((1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo(14.1.0)heptadecane-5,9-dione
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• Epothilone B, Synthetic
• UNII-UEC0H0URSE
• Epothilone B,
• Epothilone B?
• Epothilone B(Patupilone)
• EPOTHILONE B [MI]
• PATUPILONE [MART.]
• SCHEMBL3808
• PATUPILONE [WHO-DD]
• CHEMBL94657
• orb1301096
• CHEBI:94639
• GTPL13600
• GLXC-04817
• EX-A1244
• Tox21_112738
• BDBM50103627
• LMPK04000041
• NSC684363
• s1364
• Patupilone (EPO906, Epothilone B)
• AKOS015951072
• CCG-269760
• CS-0714
• DB03010
• NSC-684363
• NCGC00181131-04
• NCGC00181131-10
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• 4,17-Dioxabicyclo(1410)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1S,3S,7S,10R,11S,12S,16R)-
• 4,17-Dioxabicyclo(1410)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1S-(1R*,3R*(E),7R*,10S*,11R*,12R*,16S*))-
• AC-22614
• HY-17029
• CAS-152044-54-7
• E1378
• E6257
• NS00024956
• F17412
• F050719
• BRD-K48935217-001-01-3
• Q27093987
• (-)-Epothilone B, from Sorangium cellulosum, >=98% (HPLC)
• (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((E)-1-METHYL-2-(2-METHYL-1,3-THIAZOL-4-YL)VINYL)-4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9542	95.42%
Caco-2	-	0.7094	70.94%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Nucleus	0.8279	82.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8596	85.96%
OATP1B3 inhibitior	+	0.9183	91.83%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9790	97.90%
P-glycoprotein inhibitior	+	0.6720	67.20%
P-glycoprotein substrate	-	0.8722	87.22%
CYP3A4 substrate	+	0.6948	69.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8728	87.28%
CYP3A4 inhibition	-	0.7163	71.63%
CYP2C9 inhibition	-	0.7468	74.68%
CYP2C19 inhibition	-	0.6114	61.14%
CYP2D6 inhibition	-	0.9114	91.14%
CYP1A2 inhibition	+	0.5065	50.65%
CYP2C8 inhibition	+	0.5714	57.14%
CYP inhibitory promiscuity	-	0.8841	88.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.4898	48.98%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9384	93.84%
Skin irritation	-	0.6963	69.63%
Skin corrosion	-	0.9100	91.00%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4234	42.34%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.5709	57.09%
skin sensitisation	-	0.7952	79.52%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6821	68.21%
Acute Oral Toxicity (c)	III	0.5061	50.61%
Estrogen receptor binding	+	0.6729	67.29%
Androgen receptor binding	+	0.6626	66.26%
Thyroid receptor binding	+	0.5209	52.09%
Glucocorticoid receptor binding	+	0.7124	71.24%
Aromatase binding	+	0.7471	74.71%
PPAR gamma	+	0.6502	65.02%
Honey bee toxicity	-	0.7607	76.07%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9854	98.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.18%	99.23%
CHEMBL325	Q13547	Histone deacetylase 1	93.39%	95.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.22%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.08%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.84%	85.14%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.95%	87.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.45%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.38%	86.00%
CHEMBL230	P35354	Cyclooxygenase-2	86.39%	89.63%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.14%	97.53%
CHEMBL2581	P07339	Cathepsin D	86.04%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.00%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.88%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.98%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.53%	91.19%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.73%	96.39%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.58%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	81.07%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.86%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 448013
• LOTUS: LTS0217655
• wikiData: Q27093987