3,5,5-Trimethylcyclohex-2-enone

  • GreenMolBD CID : 54
  • Molecular Formula : C9H14O
  • Molecular Weight : 138.21
  • Exact Molecular Mass : 138.104
  • IUPAC Name : 3,5,5-trimethylcyclohex-2-en-1-one
  • InChI : InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
  • InChI Key : HJOVHMDZYOCNQW-UHFFFAOYSA-N
  • Canonical SMILES : CC1=CC(=O)CC(C1)(C)C
  • Isomeric SMILES : CC1=CC(=O)CC(C1)(C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

1.2. Taxonomy Tree

1.3. Alternative Parent

Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homomonocyclic compounds

1.5. Substituents

Cyclohexenone; Organic oxide; Hydrocarbon derivative; Aliphatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.3218 17.07 0 1 10 0 0 0 4.1779 215.14 169.85 0.64242

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-76.407353 3.51 -5.064 -10.10267 -0.0263 5.038

4. Compound Reactivity

DLP nRFG nLMR
2 0 3

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 1.48724 12146.6 0.0200957 Moderate Weak Severe Degradable 0.0710345 10.5383

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
ISOPHORONE
78-59-1
Isoacetophorone
3,5,5-Trimethylcyclohex-2-en-1-one
Isoforone
Isoforon
Izoforon
Isooctopherone
3,5,5-Trimethyl-2-cyclohexen-1-one
alpha-Isophorone
2-Cyclohexen-1-one, 3,5,5-trimethyl-
1,1,3-Trimethyl-3-cyclohexene-5-one
Isophoron
3,5,5-Trimethyl-2-cyclohexenone
3,5,5-Trimethylcyclohex-2-enone
.alpha.-Isophoron
Izoforon [Polish]
NCI-C55618
Isoforone [Italian]
Caswell No. 506
3,5,5-Trimethyl-2-cyclohexen-1-on
UNII-2BR99VR6WA
3,5,5-Trimetil-2-cicloesen-1-one
.alpha.-Isophorone
Isophorone, 97%
NSC 403657
FEMA No. 3553
CCRIS 1353
HSDB 619
ISOPHORONE, REAG
EINECS 201-126-0
EPA Pesticide Chemical Code 047401
3,5,5-Trimethyl-2-cyclohexene-1-one
BRN 1280721
3,5,5-Trimethylcyclohexenone
AI3-00046
3,5,5-Trimethylcyclohexen one
CHEBI:34800
3,5,5-Trimetil-2-cicloesen-1-one [Italian]
NSC4881
HJOVHMDZYOCNQW-UHFFFAOYSA-N
3,5,5-Trimethylcyclohexen-2-one-1
3,5,5-Trimethyl-2-cyclohexen-1-on [German, Dutch]
1,5,5-Trimethyl-1-cyclohexen-3-one
3,3,5-Trimethyl-2-cyclohexen-1-one
DSSTox_CID_759
ST50330654
DSSTox_RID_75774
DSSTox_GSID_20759
3,5-Trimethyl-2-cyclohexenone
3,5-Trimetil-2-cicloesen-1-one
3,5-Trimethyl-2-cyclohexen-1-one
Isophorone-2,4,4,6,6-d5
1,3-Trimethyl-3-cyclohexene-5-one
3,5-Trimethyl-2-cyclohexene-1-one
WLN: L6V BUTJ C1 D1 D1
2-Cyclohexen-1-one,5,5-trimethyl-
CAS-78-59-1
3,5-Trimethyl-2-cyclohexen-1-on (GERMAN, DUTCH)
a-Isophorone
alpha -isophoron
alpha -isophorone
nchem.180-comp3
ACMC-209pep
Isophorone Reagent Grade
AC1L1MRJ
AC1Q2HBB
AC1Q2HBC
2BR99VR6WA
SCHEMBL22522
Isophorone, >=97%, FG
4-07-00-00165 (Beilstein Handbook Reference)
KSC377I8H
BIDD:ER0627
Isophorone, analytical standard
CHEMBL1882894
DTXSID8020759
CTK2H7483
FEMA 3553
KS-00000VXG
MolPort-000-701-433
BB_NC-0161
NSC-4881
Tox21_202312
Tox21_300050
ANW-37199
BBL027346
MFCD00001584
NSC403657
STK801792
ZINC14822379
3,5,5-trimethyl-1-cyclohex-2-enone
AKOS000120392
AKOS025243269
3,5,5-trimethylcyclohexa-2-en-1-one
LS-1750
MCULE-5564101474
NSC-403657
RL05042
RTR-025123
TRA0010206
3,3,5-trimethyl-cyclohex-5-en-1-one
3,5,5-trimethyl-cyclohex-2-en-1-one
1,1, 3-Trimethyl-3-cyclohexene-5-one
3,5, 5-Trimethyl-2-cyclohexene-1-one
NCGC00164006-01
NCGC00164006-02
NCGC00164006-03
NCGC00254115-01
NCGC00259861-01
3,3,5-trimethyl-cyclohex-5 -en-1-one
AC-10580
AN-42106
CJ-14631
K387
OR000839
OR341384
SC-74911
Isophorone, Vetec(TM) reagent grade, 97%
TR-025123
FT-0627443
I0151
C14743
A839454
I14-2746
W-104274
F0001-2053
InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H
3,5,5-Trimethycyclohex-2-enone

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
3,5,5-Trimethylcyclohex-2-enone
Abelmoschus esculentus (L.) Moench Pod 3
Biophytum sensitivum (L.) DC. 2 , 5
Cocos nucifera L. Flower; Floral Axis 3
Colocasia esculenta Linn. Cormel 2 , 5
Crocus sativus L. Stigma 13
Cucurbita maxima Duchesne Leaf 1
Mangifera indica Fruit Pulp 6
Viola odorata Leaf 5

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
56 androgen receptor AR Homo sapiens 9.9651 1259243
57 estrogen receptor 1 ESR1 Homo sapiens 0.1737 743075
57 estrogen receptor 1 ESR1 Homo sapiens 5.6038 1259244
49 estrogen receptor 2 ESR2 Homo sapiens 7.0547 1259378
49 estrogen receptor 2 ESR2 Homo sapiens 7.0547 1259377
25 estrogen related receptor alpha ESRRA Homo sapiens 14.076 1224848
25 estrogen related receptor alpha ESRRA Homo sapiens 14.076 1224849
25 estrogen related receptor alpha ESRRA Homo sapiens 70.5473 1224841
26 GLI family zinc finger 3 GLI3 Homo sapiens 31.5123 1259392
26 GLI family zinc finger 3 GLI3 Homo sapiens 79.1554 1259369
92 histone H2AX LOC100757539 Cricetulus griseus 82.3469 1224845
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 5.042 1224846
85 Jun proto-oncogene, AP-1 transcription factor subunit JUN Homo sapiens 14.2102 1159526
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 7.0547 1224838
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 15.7936 1224839
72 peroxisome proliferator activated receptor gamma PPARG Homo sapiens 50.1187 588536
50 RAR-related orphan receptor gamma Rorc Mus musculus 2.5031 1159521
51 retinoic acid receptor alpha RARA Homo sapiens 4.9944 1159552
54 retinoid X receptor alpha RXRA Homo sapiens 4.005 1159527

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
88196832MolPortSource URLSource DetailMolPort-000-701-433Source Record URL
164811329Finetech Industry LimitedSource URLSource DetailFT-0627443Source Record URL
104668815AKos Consulting & SolutionsSource URLSource DetailAKOS000120392Source Record URL
252765764AKos Consulting & SolutionsSource URLSource DetailAKOS025243269Source Record URL
297479484Aurora Fine Chemicals LLCSource URLSource DetailA13.139.334Source Record URL
223499985A&J Pharmtech CO., LTD.Source URLSource DetailCJ-14631Source Record URL
316396326abcr GmbHSource URLSource DetailAB117140Source Record URL
253653025labseekerSource URLSource DetailSC-74911Source Record URL
204370712TractusSource URLSource DetailRTR-025123Source Record URL
135568303TractusSource URLSource DetailTR-025123Source Record URL
252272109TractusSource URLSource DetailTRA0010206Source Record URL
3562657541717 CheMall CorporationSource URLSource DetailBG00600304Source Record URL
3630193991717 CheMall CorporationSource URLSource DetailBG04149141Source Record URL
3627581391717 CheMall CorporationSource URLSource DetailBG04443665Source Record URL
3603418921717 CheMall CorporationSource URLSource DetailBG07183180Source Record URL
3133583ChemExper Chemical DirectorySource URLSource DetailHeTH@@RYVZfZZj`@@Source Record URL
223681518AN PharmaTechSource URLSource DetailAN-42106Source Record URL
355250250MolMallSource URLSource Detail19983Source Record URL
160804700AnwardSource URLSource DetailANW-37199Source Record URL
162178978AK Scientific, Inc. (AKSCI)Source URLSource DetailK387Source Record URL
252351009AHH Chemical co.,ltdSource URLSource DetailMT-52946Source Record URL
24872076Sigma-AldrichSource URLSource Detail48545_SUPELCOSource Record URL
24895951Sigma-AldrichSource URLSource DetailI18709_ALDRICHSource Record URL
329830127Sigma-AldrichSource URLSource DetailV900756_VETECSource Record URL
24901777Sigma-AldrichSource URLSource DetailW355305_ALDRICHSource Record URL
342418625Wubei-BiochemSource URLSource DetailWB008240SUSource Record URL
346438039King ScientificSource URLSource DetailKS-00000VXGSource Record URL
163806516King ScientificSource URLSource DetailKSC377I8HSource Record URL
316603953ParchemSource URLSource Detail1616Source Record URL
316963501ParchemSource URLSource Detail17785Source Record URL
316605759ParchemSource URLSource Detail8370Source Record URL
126632282ChemMolSource URLSource Detail30100546Source Record URL
126687364ChemMolSource URLSource Detail49426014Source Record URL
241144335ChemMolSource URLSource Detail99153439Source Record URL
350095789DC ChemicalsSource URLSource DetailDCZ-137Source Record URL
57323528NovoSeekSource URLSource Detail6544Source Record URL
104312364ABI ChemSource URLSource DetailAC1L1MRJSource Record URL
117408235ABI ChemSource URLSource DetailAC1Q2HBBSource Record URL
117408236ABI ChemSource URLSource DetailAC1Q2HBCSource Record URL
166285097MculeSource URLSource DetailMCULE-5564101474Source Record URL
184014218Vitas-M LaboratorySource URLSource DetailBBL027346Source Record URL
85279234Vitas-M LaboratorySource URLSource DetailSTK801792Source Record URL
354321956iChemical Technology USA IncSource URLSource DetailEBD3069517Source Record URL
318497618CambridgeChemSource URLSource DetailDB11694Source Record URL
329972755CambridgeChemSource URLSource Detailwkq-02093Source Record URL
87245037ISpharmSource URLSource DetailI14-2746Source Record URL
315341292Life ChemicalsSource URLSource DetailF0001-2053Source Record URL
252403539MolepediaSource URLSource DetailM90001130PSource Record URL
59237891ZINCSource URLSource DetailZINC14822379Source Record URL
349317171Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0835313Source Record URL
162296769AchemicaSource URLSource DetailACMC-209pepSource Record URL
340509569LGC StandardsSource URLSource DetailDRE-C14446000Source Record URL
255378138BiosynthSource URLSource DetailW-104274Source Record URL
207117628Angene ChemicalSource URLSource DetailAGN-PC-0JK7N0Source Record URL
162654688ChemTikSource URLSource DetailCTK2H7483Source Record URL
143555087TimTecSource URLSource DetailST50330654Source Record URL
92710017Hangzhou APIChem TechnologySource URLSource DetailAC-10580Source Record URL
51075042MP BiomedicalsSource URLSource Detail215719Source Record URL
163819660Oakwood ProductsSource URLSource Detail094564Source Record URL
87571538TCI (Tokyo Chemical Industry)Source URLSource DetailI0151Source Record URL
346704637LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00220510Source Record URL
174530742WutechSource URLSource DetailRL05042Source Record URL
318313464Chem-Space.com DatabaseSource URLSource DetailCSC000211104Source Record URL
321915115AcadechemSource URLSource DetailACDS-033350Source Record URL
131326519Amadis ChemicalSource URLSource DetailA839454Source Record URL
162089253Chembase.cnSource URLSource Detail110614Source Record URL
355174493MuseChemSource URLSource DetailR069474Source Record URL
254784953Boc SciencesSource URLSource Detail78-59-1Source Record URL