emivirine (CHEBI:44143)

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CHEBI:44143 - emivirine

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ChEBI Name	emivirine

ChEBI ID	CHEBI:44143

Definition	A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. A non-nucleoside inhibitor of HIV-1 reverse transcriptase, emivirine was an unsuccessful experimental agent for the treatment of HIV.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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44 45 0 0 0 0 999 V2000

1.6450 0.7070 -1.0480 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2590 0.7080 -2.3760 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9140 -0.0980 -3.2870 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9550 -0.9060 -2.8710 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3420 -0.9070 -1.5440 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6900 -0.0960 -0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1170 0.7810 0.6660 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3810 0.6810 0.1510 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.3250 -0.0350 0.7860 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4400 -0.1160 0.3080 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0520 -0.6650 1.9440 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.8210 -0.5870 2.4870 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5730 -1.1570 3.5340 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1810 0.1640 1.8280 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9320 1.5870 -0.0550 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5660 0.2680 2.4140 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4970 0.9950 3.7590 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1380 -1.1340 2.6220 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7070 1.3560 -1.1070 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3900 0.4970 -2.2040 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4600 -0.4420 -2.3150 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2510 -1.3090 -3.5590 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4450 1.3400 -2.7000 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6110 -0.0970 -4.3240 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4660 -1.5370 -3.5830 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1560 -1.5390 -1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9930 -0.0970 0.4020 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7450 -1.1780 2.3900 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4570 2.4160 -0.5790 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6500 1.9770 0.6660 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2080 0.8250 1.7320 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4990 1.0710 4.1820 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0900 1.9950 3.6100 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8550 0.4380 4.4410 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4960 -1.6910 3.3040 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1870 -1.6530 1.6640 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1400 -1.0590 3.0460 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1280 2.2760 -1.1870 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7710 1.5930 -1.1270 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4070 0.0910 -2.4000 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4800 -1.0770 -1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0670 -2.0260 -3.6430 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2310 -0.6750 -4.4450 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3050 -1.8440 -3.4740 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 4 0 0 0 0

1 6 4 0 0 0 0

1 15 1 0 0 0 0

2 3 4 0 0 0 0

2 23 1 0 0 0 0

3 4 4 0 0 0 0

3 24 1 0 0 0 0

4 5 4 0 0 0 0

4 25 1 0 0 0 0

5 6 4 0 0 0 0

5 26 1 0 0 0 0

6 27 1 0 0 0 0

7 8 1 0 0 0 0

7 14 2 0 0 0 0

7 15 1 0 0 0 0

8 9 1 0 0 0 0

8 19 1 0 0 0 0

9 10 2 0 0 0 0

9 11 1 0 0 0 0

11 12 1 0 0 0 0

11 28 1 0 0 0 0

12 13 2 0 0 0 0

12 14 1 0 0 0 0

14 16 1 0 0 0 0

15 29 1 0 0 0 0

15 30 1 0 0 0 0

16 17 1 0 0 0 0

16 18 1 0 0 0 0

16 31 1 0 0 0 0

17 32 1 0 0 0 0

17 33 1 0 0 0 0

17 34 1 0 0 0 0

18 35 1 0 0 0 0

18 36 1 0 0 0 0

18 37 1 0 0 0 0

19 20 1 0 0 0 0

19 38 1 0 0 0 0

19 39 1 0 0 0 0

20 21 1 0 0 0 0

21 22 1 0 0 0 0

21 40 1 0 0 0 0

21 41 1 0 0 0 0

22 42 1 0 0 0 0

22 43 1 0 0 0 0

22 44 1 0 0 0 0

M END): 17 ms

reading 44 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

44 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C17H22N2O3

Net Charge

Average Mass

302.36820

Monoisotopic Mass

302.16304

InChI

InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

InChIKey

MLILORUFDVLTSP-UHFFFAOYSA-N

SMILES

CCOCn1c(Cc2ccccc2)c(C(C)C)c(=O)[nH]c1=O

Roles Classification
Biological Role(s):	HIV-1 reverse transcriptase inhibitor An entity which inhibits the activity of HIV-1 reverse transcriptase. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

Application(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	emivirine (CHEBI:44143) has functional parent uracil (CHEBI:17568) emivirine (CHEBI:44143) has role antiviral drug (CHEBI:36044) emivirine (CHEBI:44143) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756) emivirine (CHEBI:44143) is a pyrimidone (CHEBI:38337)

IUPAC Name

6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione

INN	Source
emivirine	ChemIDplus

Synonyms	Sources
1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione	ChEBI
6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil	ChEBI
6-BENZYL-1-ETHOXYMETHYL-5-ISOPROPYL URACIL	PDBeChem
MKC-442	ChemIDplus

Brand Name	Source
Coactinon	KEGG DRUG

Manual Xrefs	Databases
D01055	KEGG DRUG
MKC	PDBeChem
View more database links

Registry Numbers	Types	Sources
149950-60-7	CAS Registry Number	ChemIDplus
7340168	Reaxys Registry Number	Reaxys

Citations	Types	Sources
10602732	PubMed citation	Europe PMC
16898805	PubMed citation	Europe PMC
17388601	PubMed citation	Europe PMC

Last Modified

02 August 2011

CHEBI:44143 - emivirine

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