beta-Damascenone

  • GreenMolBD CID : 73
  • Molecular Formula : C13H18O
  • Molecular Weight : 190.286
  • Exact Molecular Mass : 190.136
  • IUPAC Name : (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
  • InChI : InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
  • InChI Key : POIARNZEYGURDG-FNORWQNLSA-N
  • Canonical SMILES : CC=CC(=O)C1=C(C=CCC1(C)C)C
  • Isomeric SMILES : C/C=C/C(=O)C1=C(C=CCC1(C)C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'.

1.3. Alternative Parent

Acryloyl compounds; Ketones; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homomonocyclic compounds

1.5. Substituents

Enone; Acryloyl-group; Ketone; Organic oxide; Hydrocarbon derivative; Aliphatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
3.4342 17.07 0 1 14 2 0 0 6.0059 301.053 235.931 0.632068

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-43.655063 2.6 -4.647 -9.14463 -0.14913 4.498

4. Compound Reactivity

DLP nRFG nLMR
1 1 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 0.602841 6728.9 0.0117066 Moderate Strong Severe Degradable 0.00900335 5.71389

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes Yes Yes

7. Synonyms

Name
Damascenone
beta-Damascenone
23696-85-7
trans-beta-Damascenone
23726-93-4
trans-damascenone
.beta.-Damascenone
1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
POIARNZEYGURDG-FNORWQNLSA-N
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
(E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-one
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
(E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-
2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene
1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2E-buten-1-one
2-BUTEN-1-ONE, 1-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL)-
Damascenone (natural)
fermentone
UNII-U66V25TBO0
Doricenone
b-damascenone
FEMA No. 3420
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (2E)-
beta -damascenone
EINECS 245-833-2
EINECS 245-844-2
Damascenone, trans-
(E)-beta-damascenone
beta-(E)-damascenone
AC1NSMVF
(e)-beta -damascenone
beta -(e)-damascenone
Trans-beta -damascenone
trans-.beta.-Damascenone
(E)-.beta.-Damascenone
.beta.-(E)-Damascenone
DSSTox_CID_21397
DSSTox_GSID_41397
SCHEMBL80947
2-Buten-1-one,1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-
DISCONTINUED, UNSTABLE"
3,5,8-Megastigmatrien-7-one
trans-2,6,6-Trimethyl-1-crotonylcyclohexa-1,3-diene
U66V25TBO0
Damascenone, analytical standard
CHEMBL3733030
CHEBI:67251
MolPort-003-846-126
Tox21_304001
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)
LMPR01070304
AKOS015914961
ZINC100070359
NCGC00357220-01
AJ-53224
AK122851
AN-17999
OR020659
OR245886
CAS-23696-85-7
RT-004632
1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene
2,6,6-trimethyl-1-crotonoyl-1,3-cyclohexadiene
A816852
C-27419
Damascenone, certified reference material, TraceCERT(R)
4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl)but-2-en-4-one
(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
(E)-1-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)-2-buten-1-one
Damascenone, natural, 1.1-1.3 wt. % (190 proof ethanol), FG
(2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one
1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, trans-
36649-63-5

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
beta-Damascenone
Abelmoschus esculentus (L.) Moench Pod 3
Lantana camara L Leaf and Flower 12
Litchi chinensis Fruit 8 , 11
Mangifera indica Fruit 7
Olea europea Leaf 2

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
25 estrogen related receptor alpha ESRRA Homo sapiens 8.6349 1224841
26 GLI family zinc finger 3 GLI3 Homo sapiens 6.11306 1259392
26 GLI family zinc finger 3 GLI3 Homo sapiens 54.4827 1259369

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
131306587Amadis ChemicalSource URLSource DetailA816852Source Record URL
347735342Yuhao ChemicalSource URLSource DetailRT0406Source Record URL
347735337Yuhao ChemicalSource URLSource DetailXJ4723Source Record URL
252448568MolepediaSource URLSource DetailM92014741PSource Record URL
329756066Sigma-AldrichSource URLSource Detail41163_SIALSource Record URL
340469783Sigma-AldrichSource URLSource Detail92299_SIALSource Record URL
24901692Sigma-AldrichSource URLSource DetailW342017_ALDRICHSource Record URL
126672436ChemMolSource URLSource Detail49411085Source Record URL
241042938ChemMolSource URLSource Detail99052042Source Record URL
241043074ChemMolSource URLSource Detail99052178Source Record URL
355159064MuseChemSource URLSource DetailR064347Source Record URL
350090147DC ChemicalsSource URLSource DetailDCT-036Source Record URL
254771506Boc SciencesSource URLSource Detail23696-85-7Source Record URL
254771536Boc SciencesSource URLSource Detail23726-93-4Source Record URL
318270650Chem-Space.com DatabaseSource URLSource DetailCSC000060976Source Record URL
318356257CambridgeChemSource URLSource DetailCB21256Source Record URL
310125791Aurora Fine Chemicals LLCSource URLSource DetailA17.898.074Source Record URL
314943015ChemhereSource URLSource DetailAchem567546Source Record URL
319548072Oakwood ProductsSource URLSource Detail429823Source Record URL
318024368iChemical Technology USA IncSource URLSource DetailEBD18286Source Record URL
354309848iChemical Technology USA IncSource URLSource DetailEBD3324418Source Record URL
3596987411717 CheMall CorporationSource URLSource DetailBG06542920Source Record URL
3604988351717 CheMall CorporationSource URLSource DetailBG07340123Source Record URL
268761654ZINCSource URLSource DetailZINC100070359Source Record URL
348919489Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0437640Source Record URL
368233975AmbinterSource URLSource DetailAmb17611555Source Record URL
316963932ParchemSource URLSource Detail19620Source Record URL
57362259NovoSeekSource URLSource Detail5366074Source Record URL
114158995ABI ChemSource URLSource DetailAC1NSMVFSource Record URL
347758296Alfa ChemistrySource URLSource Detail23726-93-4Source Record URL
152054380AKos Consulting & SolutionsSource URLSource DetailAKOS015914961Source Record URL
223562395A&J Pharmtech CO., LTD.Source URLSource DetailAJ-53224Source Record URL
275927595BePharm Ltd.Source URLSource DetailB247029Source Record URL
204376792TractusSource URLSource DetailRT-004632Source Record URL
162221186Chembase.cnSource URLSource Detail126859Source Record URL
223665279AN PharmaTechSource URLSource DetailAN-17999Source Record URL
252363813AHH Chemical co.,ltdSource URLSource DetailMT-07454Source Record URL