EVP

(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside

Created:	2011-03-23
Last modified:	2020-06-05

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13 entries where EVP is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	74
Chiral Atom Count	10
Bond Count	80
Aromatic Bond Count	12

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Chemical Component Summary
Name	(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
Synonyms	Etoposide; VP-16
Systematic Name (OpenEye OEToolkits)	(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-2-methyl-7,8-bis(oxidanyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(3,5-dimethoxy-4-oxidanyl-phenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Formula	C₂₉ H₃₂ O₁₃
Molecular Weight	588.557
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C1OCC7C1C(c2cc(OC)c(O)c(OC)c2)c4cc3OCOc3cc4C7OC6OC5C(OC(OC5)C)C(O)C6O
SMILES	CACTVS	3.370	COc1cc(cc(OC)c1O)[CH]2[CH]3[CH](COC3=O)[CH](O[CH]4O[CH]5CO[CH](C)O[CH]5[CH](O)[CH]4O)c6cc7OCOc7cc26
SMILES	OpenEye OEToolkits	1.7.2	CC1OCC2C(O1)C(C(C(O2)OC3c4cc5c(cc4C(C6C3COC6=O)c7cc(c(c(c7)OC)O)OC)OCO5)O)O
Canonical SMILES	CACTVS	3.370	COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26
Canonical SMILES	OpenEye OEToolkits	1.7.2	C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@@H]3c4cc5c(cc4[C@H]([C@@H]6[C@@H]3COC6=O)c7cc(c(c(c7)OC)O)OC)OCO5)O)O
InChI	InChI	1.03	InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey	InChI	1.03	VJJPUSNTGOMMGY-MRVIYFEKSA-N

Drug Info: DrugBank

DrugBank ID	DB00773
Name	Etoposide
Groups	approved
Description	A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.
Synonyms	Etoposido trans-Etoposide 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside) 4-demethylepipodophyllotoxin β-D-ethylideneglucoside Etoposidum Etoposide Etoposide phosphate 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5aH)-one (−)-etoposide
Brand Names	Dom-etoposide Vepesid Inj 20mg/ml PMS-etoposide Etoposide Injection USP VePesid Etoposide - Liq IV 20mg/ml Toposar Etoposide Injection, USP Etoposide Eposin Etoposide Injection Etopophos
Indication	For use in combination with other chemotherapeutic agents in the treatment of refractory testicular tumors and as first line treatment in patients with small cell lung cancer. Also used to treat other malignancies such as lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme.
Categories	Antineoplastic Agents Antineoplastic Agents, Phytogenic Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Substrates Carbohydrates Cardiotoxic antineoplastic agents Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Enzyme Inhibitors Glucosides Glycosides Immunosuppressive Agents Myelosuppressive Agents Naphthalenes Narrow Therapeutic Index Drugs P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Podophyllotoxin Podophyllotoxin Derivatives Tetrahydronaphthalenes Topoisomerase II Inhibitors Topoisomerase Inhibitors UGT1A1 Substrates UGT1A1 Substrates with a Narrow Therapeutic Index
ATC-Code	L01CB01
CAS number	33419-42-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
DNA topoisomerase 2-alpha	MEVSPLQPVNENMQVNKIKKNEDAKKRLSVERIYQKKTQLEHILLRPDTY...	unknown	inhibitor
DNA topoisomerase 2-beta	MAKSGGCGAGAGVGGGNGALTWVTLFDQNNAAKKEESETANKNDSSKKLS...	unknown	inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	substrate
Glutathione S-transferase theta-1	MGLELYLDLLSQPCRAVYIFAKKNDIPFELRIVDLIKGQHLSDAFAQVNP...	unknown	substrate
Glutathione S-transferase P	MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKASCLY...	unknown	substrate
Prostaglandin G/H synthase 2	MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...	unknown	substrate
Prostaglandin G/H synthase 1	MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor,inducer
Canalicular multispecific organic anion transporter 2	MDALCGSGELGSKFWDSNLSVHTENPDLTPCFQNSLLAWVPCIYLWVALP...	unknown	substrate,inhibitor
Multidrug resistance-associated protein 6	MAAPAEPCAGQGVWNQTEPEPAATSLLSLCFLRTAGVWVPPMYLWVLGPI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	substrate,inhibitor
Multidrug resistance-associated protein 7	MERLLAQLCGSSAAWPLPLWEGDTTGHCFTQLVLSALPHALLAVLSACYL...	unknown	substrate,inhibitor
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate,inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682