rotenone (CHEBI:28201)

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CHEBI:28201 - rotenone

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ChEBI Name	rotenone

ChEBI ID	CHEBI:28201

Definition	A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).

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

Secondary ChEBI IDs	CHEBI:8897, CHEBI:26583

Supplier Information	ZINC000085552652

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

970 - Ideal conformer

Mrv1927 05282121213D

starting HoverWatcher_5

Time for openFile(970 - Ideal conformer

Mrv1927 05282121213D

51 55 0 0 0 0 999 V2000

-1.2840 2.5120 0.9010 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0300 -0.5500 -3.2560 C 0 0 1 0 0 0 0 0 0 0 0 0

2.2080 -0.9550 -1.2120 C 0 0 0 0 0 0 0 0 0 0 0 0

3.5670 0.0040 1.0110 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7960 0.8590 0.2430 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1170 0.3830 -0.8660 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5570 2.2890 -0.7640 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.3840 -0.7160 -0.3620 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.5630 -1.5120 0.6200 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.0630 -2.5920 1.1680 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.1670 -1.0650 0.9710 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.2690 -1.0300 -0.2920 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.4210 0.1850 -0.0360 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.0310 0.9060 0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.1660 0.3070 1.4090 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4490 2.0860 1.4840 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6840 1.8040 -0.1420 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2500 0.6070 -0.6320 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6620 -0.0960 -1.6160 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2580 0.5480 -2.5010 C 0 0 1 0 0 0 0 0 0 0 0 0

1.5510 -1.4630 -2.2890 O 0 0 0 0 0 0 0 0 0 0 0 0

2.9840 -1.8160 -0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0

3.6620 -1.3410 0.6650 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2880 1.3380 -1.6810 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9770 3.4070 -0.5490 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2320 0.4770 2.1000 O 0 0 0 0 0 0 0 0 0 0 0 0

4.0890 1.8680 2.3940 C 0 0 0 0 0 0 0 0 0 0 0 0

4.4200 -2.1850 1.4140 O 0 0 0 0 0 0 0 0 0 0 0 0

4.4710 -3.5520 0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8210 3.4210 1.2550 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3560 -1.0740 -3.9330 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8480 -0.1030 -3.8200 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7230 1.9030 0.5110 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8690 -0.6820 -1.3220 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.3580 -1.1890 -0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.5180 0.2980 0.0140 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.4740 -3.1620 1.8720 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.0630 -2.9110 0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7370 -1.7140 1.7340 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6540 -1.9280 -0.3580 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8690 -0.9040 -1.1940 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9040 2.6410 2.2910 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2700 1.1970 -3.2000 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0570 -2.8590 -0.7120 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9340 1.9010 -2.3540 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6680 2.1130 3.2840 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4520 2.4570 1.5510 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0380 2.0960 2.5700 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4660 -3.9730 1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8780 -3.6100 -0.0100 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1080 -4.1150 1.6810 H 0 0 0 0 0 0 0 0 0 0 0 0

8 9 1 0 0 0 0

10 9 2 3 0 0 0

9 11 1 0 0 0 0

11 15 1 0 0 0 0

11 12 1 0 0 0 0

15 14 1 0 0 0 0

12 13 1 0 0 0 0

14 13 2 0 0 0 0

14 16 1 0 0 0 0

13 18 1 0 0 0 0

16 1 2 0 0 0 0

18 19 1 0 0 0 0

18 17 2 0 0 0 0

19 20 1 0 0 0 0

20 2 1 0 0 0 0

20 24 1 0 0 0 0

2 21 1 0 0 0 0

1 17 1 0 0 0 0

17 7 1 0 0 0 0

24 7 1 0 0 0 0

24 6 1 0 0 0 0

21 3 1 0 0 0 0

7 25 2 0 0 0 0

6 3 2 0 0 0 0

6 5 1 0 0 0 0

3 22 1 0 0 0 0

22 23 2 0 0 0 0

5 4 2 0 0 0 0

23 4 1 0 0 0 0

23 28 1 0 0 0 0

4 26 1 0 0 0 0

28 29 1 0 0 0 0

26 27 1 0 0 0 0

1 30 1 0 0 0 0

2 31 1 0 0 0 0

2 32 1 0 0 0 0

5 33 1 0 0 0 0

8 34 1 0 0 0 0

8 35 1 0 0 0 0

8 36 1 0 0 0 0

10 37 1 0 0 0 0

10 38 1 0 0 0 0

11 39 1 1 0 0 0

12 40 1 0 0 0 0

12 41 1 0 0 0 0

16 42 1 0 0 0 0

20 43 1 6 0 0 0

22 44 1 0 0 0 0

24 45 1 6 0 0 0

27 46 1 0 0 0 0

27 47 1 0 0 0 0

27 48 1 0 0 0 0

29 49 1 0 0 0 0

29 50 1 0 0 0 0

29 51 1 0 0 0 0

M END): 19 ms

reading 51 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

51 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
A triglyceride (from tri- and glyceride; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver and are a major component of human skin oils. Many types of triglycerides exist. One specific classification focuses on saturated and unsaturated types. Saturated fats have no C=C groups; unsaturated fats feature one or more C=C groups. Unsaturated fats tend to have a lower melting point than saturated analogues; as a result, they are often liquid at room temperature.
Read full article at Wikipedia

Formula

C23H22O6

Net Charge

Average Mass

394.423

Monoisotopic Mass

394.14164

InChI

InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChIKey

JUVIOZPCNVVQFO-HBGVWJBISA-N

SMILES

[H][C@@]1(CC2=C3O[C@]4([H])COC5=C(C=C(OC)C(OC)=C5)[C@]4([H])C(=O)C3=CC=C2O1)C(C)=C

Metabolite of Species	Details
Mundulea chapelieri (IPNI:20004737-1)	Found in flower (BTO:0000469). See: PubMed
Mundulea chapelieri (IPNI:20004737-1)	Found in leaf (BTO:0000713). See: PubMed
Mundulea chapelieri (IPNI:20004737-1)	Found in bark (BTO:0001301). See: PubMed
Erycibe expansa (IPNI:267866-1)	Found in stem (BTO:0001300). See: PubMed
Antheroporum pierrei (IPNI:474590-1)	Found in twig (BTO:0001411). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Antheroporum pierrei (IPNI:474590-1)	Found in leaf (BTO:0000713). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Derris elliptica (NCBI:txid56063)	See: DOI

Roles Classification
Biological Role(s):	toxin Poisonous substance produced by a biological organism such as a microbe, animal or plant. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. mitochondrial NADH:ubiquinone reductase inhibitor

Application(s):	piscicide A substance which is poisonous to fish and is primarily used to eliminate dominant species of fish in water. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. phytogenic insecticide An insecticide compound naturally occurring in plants.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	rotenone (CHEBI:28201) has role antineoplastic agent (CHEBI:35610) rotenone (CHEBI:28201) has role metabolite (CHEBI:25212) rotenone (CHEBI:28201) has role mitochondrial NADH:ubiquinone reductase inhibitor (CHEBI:38498) rotenone (CHEBI:28201) has role phytogenic insecticide (CHEBI:22917) rotenone (CHEBI:28201) has role piscicide (CHEBI:167183) rotenone (CHEBI:28201) has role toxin (CHEBI:27026) rotenone (CHEBI:28201) is a organic heteropentacyclic compound (CHEBI:38164) rotenone (CHEBI:28201) is a rotenones (CHEBI:72581)

IUPAC Name

(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Synonyms	Sources
(−)-cis-rotenone	ChemIDplus
(−)-rotenone	ChemIDplus
(12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one	ChEBI
5'β-rotenone	NIST Chemistry WebBook
[2R-(2α,6aα,12aα)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-one	NIST Chemistry WebBook
barbasco	ChemIDplus
canex	ChemIDplus
dactinol	ChemIDplus
Derris	ChEBI
noxfire	ChemIDplus
paraderil	ChemIDplus
Rotenone	KEGG COMPOUND
tubatoxin	ChemIDplus

Manual Xrefs	Databases
587	BPDB
587	VSDB
970	PDBeChem
C00002568	KNApSAcK
C07593	KEGG COMPOUND
CN102007944	Patent
CN102090406	Patent
DB11457	DrugBank
FDB012837	FooDB
HMDB0034436	HMDB
LMPK12060007	LIPID MAPS
LSM-5260	LINCS
Rotenone	Wikipedia
View more database links

Registry Numbers	Types	Sources
83-79-4	CAS Registry Number	ChemIDplus
83-79-4	CAS Registry Number	NIST Chemistry WebBook
99070	Reaxys Registry Number	Reaxys

Citations

Last Modified

28 May 2021

CHEBI:28201 - rotenone

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