Oseltamivir

Details

• Internal ID: c4f48521-6bbc-4290-86d0-6df328a3a4d8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Amino acids and derivatives > Gamma amino acids and derivatives
• IUPAC Name: ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
• SMILES (Canonical): CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC
• SMILES (Isomeric): CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC
• InChI: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
• InChI Key: VSZGPKBBMSAYNT-RRFJBIMHSA-N
• Popularity: 8,404 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₈N₂O₄
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.20490738 g/mol
• Topological Polar Surface Area (TPSA): 90.60 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 196618-13-0
• Tamvir
• Tamiflu
• Tamiflu-Free
• GS-4104
• (-)-oseltamivir
• GS 4104
• ebilfumin
• oseltamivirum
• Agucort
• GS4104
• Oseltamivir [INN:BAN]
• HSDB 7433
• Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• Ro-640796
• Ro-64-0796
• Agucort (TN)
• Oseltamivir (INN)
• Ro 640796
• UNII-20O93L6F9H
• (3R,4R,5S)-Ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
• CHEBI:7798
• GS-4071 ETHYL ESTER
• GOP-A-Flu
• 20O93L6F9H
• Tamiflu (*Phosphate salt 1:1*)
• RO64-0796
• 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3alpha,4beta,5alpha))-
• DTXSID9044291
• RO640796
• Oseltamivir 100 microg/mL in Acetonitrile
• OSELTAMIVIR [INN]
• Tamiflu (TN)
• ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxy-cyclohexene-1-carboxylate
• C16H28N2O4
• ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• Ethyl (5S,3R,4R)-4-(acetylamino)-5-amino-3-(ethylpropoxy)cyclohex-1-enecarboxylate
• 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-
• SR-05000001499
• oseltamivir-phosphate
• OSELTAMIVIR [MI]
• GS 4104;GOP-A-Flu;GS-4104;Tamiflu-Free;Tamvir
• OSELTAMIVIR [HSDB]
• D0O5NK
• OSELTAMIVIR [VANDF]
• CHEMBL1229
• SCHEMBL32035
• OSELTAMIVIR [WHO-DD]
• BIDD:GT0426
• OSELTAMIVIR [EMA EPAR]
• BDBM5025
• DTXCID7024291
• GTPL11427
• J05AH02
• VSZGPKBBMSAYNT-RRFJBIMHSA-N
• HMS2090C11
• EX-A3415
• AKOS015843442
• AKOS015960501
• C16-H28-N2-O4
• CS-0552
• DB00198
• DT-0013
• ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohexene-1-carboxylate
• NCGC00095191-06
• NCGC00095191-12
• NCGC00095191-16
• NCGC00178698-01
• NCGC00178698-02
• NCGC00178698-04
• HY-13317
• LS-57422
• O0591
• C08092
• D08306
• E84533
• AB00173476-02
• AB00173476_04
• Q211509
• SR-05000001499-1
• BRD-K76011241-045-01-5
• 4-Acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid
• (3R,4R,5S)-4-Acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid
• Ethyl (3R, 4R, 5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• (3R,4R,5S)-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester
• (3r,4r,5s)-4-acetylamino-5-amino-3(1-ethylpropoxy) -1-cyclohexene-1-carboxylic acid ethyl ester
• (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester
• (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethyl-propoxy)cyclohex-1-enecarboxylic acid ethyl ester
• OTV

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.5220	52.20%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7419	74.19%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8885	88.85%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.7272	72.72%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8025	80.25%
P-glycoprotein inhibitior	-	0.8212	82.12%
P-glycoprotein substrate	+	0.6167	61.67%
CYP3A4 substrate	+	0.5375	53.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8457	84.57%
CYP3A4 inhibition	-	0.8364	83.64%
CYP2C9 inhibition	-	0.8774	87.74%
CYP2C19 inhibition	-	0.6677	66.77%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8367	83.67%
CYP2C8 inhibition	-	0.7173	71.73%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7817	78.17%
Carcinogenicity (trinary)	Non-required	0.6505	65.05%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9764	97.64%
Skin irritation	-	0.8073	80.73%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6572	65.72%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5097	50.97%
skin sensitisation	-	0.8674	86.74%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6514	65.14%
Acute Oral Toxicity (c)	III	0.6332	63.32%
Estrogen receptor binding	+	0.5470	54.70%
Androgen receptor binding	-	0.8513	85.13%
Thyroid receptor binding	-	0.5060	50.60%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6021	60.21%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8974	89.74%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9122	91.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.79%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.62%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.51%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.69%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.43%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.31%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.89%	90.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.96%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.57%	93.56%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 65028
• NPASS: NPC469895
• ChEMBL: CHEMBL1229
• LOTUS: LTS0229483
• wikiData: Q211509