Epothilone D

Details

• Internal ID: 3c380a4d-2cbe-4ac5-8d3c-e50c9a576cd5
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Epothilones and analogues
• IUPAC Name: (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• InChI: InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
• InChI Key: XOZIUKBZLSUILX-GIQCAXHBSA-N
• Popularity: 303 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₁NO₅S
• Molecular Weight: 491.70 g/mol
• Exact Mass: 491.27054458 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 5.27
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Desoxyepothilone b
• 189453-10-9
• (-)-Desoxyepothilone B
• 12,13-Desoxyepothilone B
• KOS-862
• (-)-Epothilone D
• NSC-703147
• KOS 862
• Epothilon D
• 12,13-Deoxyepothilone B
• Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-
• NSC 703147
• T0358E0YUF
• 12,13-desoxyepothilone b, cis
• CHEBI:29579
• (4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione
• R1492
• EPD
• UNII-T0358E0YUF
• epothilone-D
• Epothiolone D
• dEpoB
• DEpoB cpd
• OXACYCLOHEXADEC-13-ENE-2,6-DIONE, 4,8-DIHYDROXY-5,5,7,9,13-PENTAMETHYL-16-((1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL)-, (4S,7R,8S,9S,13Z,16S)-
• Epo D
• Epothilone B, desoxy
• EPOTHILONE D [MI]
• SCHEMBL4415
• 12,13-Desoxy-Epothilone B
• CHEMBL96172
• Z-12,13-desoxyepothilone B
• EPOTHILONE D [WHO-DD]
• KOS862
• DTXSID70880053
• EX-A495
• XOZIUKBZLSUILX-GIQCAXHBSA-N
• Biologically synthesized Epothilone D
• LMPK04000001
• MFCD27976357
• NSC703147
• NSC721085
• AKOS025401598
• AM81237
• CS-0655
• DB01873
• NSC-721085
• (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]-1-oxacyclohexadec-13-ene-2,6-dione
• AC-22616
• HY-15278
• A880448
• (4S,7R,8S,9s,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-oxacyclohexadec-13-ene-2,6-dione
• (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]oxacyclohexadec-13-ene-2,6-dione
• (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione
• (4S-(4R*,8R*,9R*,13Z,16R*(E)))-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)oxacyclohexadec-13-ene-2,6-dione
• Desoxyepothilone B; (3S,7S,14S,15S,16R)-3,15-Dihydroxy-2,2,10,14,16-pentamethyl-7-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-6-oxacyclohexadec-9-ene-1,5-dione
• Oxacyclohexadec-13-ene-2,6-dione, 4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4S,7R,8S,9S,13Z,16S)-
• Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4S-(4R*,7S,8R*,9R*,13Z,16R*(E)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9529	95.29%
Caco-2	-	0.6553	65.53%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Nucleus	0.8371	83.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8530	85.30%
OATP1B3 inhibitior	+	0.9113	91.13%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9893	98.93%
P-glycoprotein inhibitior	+	0.7042	70.42%
P-glycoprotein substrate	-	0.6177	61.77%
CYP3A4 substrate	+	0.6719	67.19%
CYP2C9 substrate	-	0.6236	62.36%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.8350	83.50%
CYP2C9 inhibition	-	0.7697	76.97%
CYP2C19 inhibition	-	0.6120	61.20%
CYP2D6 inhibition	-	0.9200	92.00%
CYP1A2 inhibition	-	0.5443	54.43%
CYP2C8 inhibition	+	0.5320	53.20%
CYP inhibitory promiscuity	-	0.8559	85.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5162	51.62%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9504	95.04%
Skin irritation	-	0.6903	69.03%
Skin corrosion	-	0.9147	91.47%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7683	76.83%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5967	59.67%
skin sensitisation	-	0.7945	79.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4639	46.39%
Acute Oral Toxicity (c)	III	0.4950	49.50%
Estrogen receptor binding	+	0.6237	62.37%
Androgen receptor binding	+	0.6273	62.73%
Thyroid receptor binding	-	0.4913	49.13%
Glucocorticoid receptor binding	+	0.6704	67.04%
Aromatase binding	+	0.6389	63.89%
PPAR gamma	+	0.6147	61.47%
Honey bee toxicity	-	0.7818	78.18%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9849	98.49%

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	95.05%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.48%	95.56%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	92.03%	87.67%
CHEMBL325	Q13547	Histone deacetylase 1	89.74%	95.92%
CHEMBL3401	O75469	Pregnane X receptor	87.17%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.03%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.07%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.36%	86.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.78%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.91%	93.56%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.21%	96.39%
CHEMBL340	P08684	Cytochrome P450 3A4	81.03%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.87%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 447865
• LOTUS: LTS0018469
• wikiData: Q74417010