Geranylacetone

Details

• Internal ID: 3f4e756e-3819-4a70-8595-fb87de1d829f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Acyclic monoterpenoids
• IUPAC Name: (5E)-6,10-dimethylundeca-5,9-dien-2-one
• InChI: InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+
• InChI Key: HNZUNIKWNYHEJJ-FMIVXFBMSA-N
• Popularity: 793 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.31 g/mol
• Exact Mass: 194.167065321 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• Geranyl acetone
• 3796-70-1
• 689-67-8
• (5E)-6,10-dimethylundeca-5,9-dien-2-one
• (E)-6,10-Dimethylundeca-5,9-dien-2-one
• 5,9-Undecadien-2-one, 6,10-dimethyl-
• trans-Geranylacetone
• cis,trans-Geranylacetone
• 6,10-Dimethyl-5,9-undecadien-2-one
• (E)-6,10-Dimethyl-5,9-undecadien-2-one
• (E)-geranylacetone
• Dihydropseudoionone
• FEMA No. 3542
• 5,9-Undecadien-2-one, 6,10-dimethyl-, (E)-
• 5,9-Undecadien-2-one, 6,10-dimethyl-, (5E)-
• (E/Z)-Geranylacetone
• 9B7RY79U9Z
• trans-6,10-Dimethyl-5,9-undecadien-2-one
• 6,10-Dimethyl-5(E),9-undecadien-2-one
• 6,10-dimethyl-(E)-5,9-undecadien-2-one
• MFCD00008910
• 6,10-dimethyl-5,9-undecadiene-2-one
• DTXCID901586
• DTXSID1021586
• Geranylacetone, trans-
• .alpha.,.beta.-Dihydropseudoionone
• Geranylacetone(Z/E)
• NSC 406679
• 2,6-dimethylundeca-2,6-dien-10-one
• 6,10-Dimethyl-undeca-5,9-dien-2-one
• CAS-689-67-8
• (5E)-6,10-dimethyl-2-undeca-5,9-dienone
• (5E)-6,10-Dimethyl-5,9-undecadien-2-one
• EINECS 223-269-8
• UNII-9B7RY79U9Z
• E-geranylacetone
• Undecadien-2-one, 6,10-dimethyl-
• 2,6-Dimethyl-2,6-undecadien-2-one, trans-
• 6,10-Dimethyl-5,9-undecadien-2-one, trans-
• E-geranyl acetone
• 6,10-Dimethyl-5,9-undecadien-2-one, (E)-
• 68228-05-7
• Dihydropseudoionone; 6,10-Dimethyl-5,9-undecadien-2-one; 2,6-Dimethylundeca-2,6-dien-10-one; 6,10-Dimethyl-5,9-undec-2-one; 6,10-Dimethyl-5,9-undecadiene-2-one;
• Geranyl-2-propanone
• (E)-geranyl-acetone
• 5, 6,10-dimethyl-
• SCHEMBL112855
• orb1685430
• DTXSID4052053
• SCHEMBL10501221
• SCHEMBL28662939
• CHEBI:67206
• HY-N8446
• EINECS 269-400-2
• Tox21_202156
• Tox21_302933
• AC1127
• BBL027735
• LMFA11000696
• MSK014213
• NSC406679
• SBB001603
• STK709221
• 6,10-dimethyl-5,9-undecadien-2-on
• AKOS005522601
• NSC-406679
• NCGC00249179-01
• NCGC00256556-01
• NCGC00259705-01
• TS-09793
• GERANYLACETONE (MIXTURE OF ISOMERS)
• (5E)-6,10-dimethyl-5,9-undecen-2-one
• HY-142037
• ST4049797
• CS-0144246
• CS-0343195
• G0236
• NS00010772
• EN300-125485
• F619444
• SR-01000526349
• SR-01000526349-1
• 6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE [FHFI]
• Q27135687
• 6,10-Dimethylundeca-5,9-dien-2-one (mixture of isomers)
• 6,10-Dimethyl-5,9-undecadien-2-one, >=97%, stabilized, FG
• Geranylacetone, (E)+(Z), 97%, (Z)-isomer (nerylacetone) ca 45%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.9623	96.23%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Nucleus	0.4369	43.69%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9491	94.91%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6026	60.26%
P-glycoprotein inhibitior	-	0.9656	96.56%
P-glycoprotein substrate	-	0.9782	97.82%
CYP3A4 substrate	-	0.6536	65.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7774	77.74%
CYP3A4 inhibition	-	0.9623	96.23%
CYP2C9 inhibition	-	0.9086	90.86%
CYP2C19 inhibition	-	0.9062	90.62%
CYP2D6 inhibition	-	0.9612	96.12%
CYP1A2 inhibition	-	0.5346	53.46%
CYP2C8 inhibition	-	0.9859	98.59%
CYP inhibitory promiscuity	-	0.7543	75.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5600	56.00%
Carcinogenicity (trinary)	Non-required	0.6029	60.29%
Eye corrosion	+	0.6517	65.17%
Eye irritation	+	0.9628	96.28%
Skin irritation	+	0.8176	81.76%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6282	62.82%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.9472	94.72%
Respiratory toxicity	-	0.9444	94.44%
Reproductive toxicity	-	0.9889	98.89%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.6592	65.92%
Acute Oral Toxicity (c)	III	0.8221	82.21%
Estrogen receptor binding	-	0.9393	93.93%
Androgen receptor binding	-	0.9208	92.08%
Thyroid receptor binding	-	0.8763	87.63%
Glucocorticoid receptor binding	-	0.6568	65.68%
Aromatase binding	-	0.8446	84.46%
PPAR gamma	-	0.6925	69.25%
Honey bee toxicity	-	0.9198	91.98%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9240	92.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.15%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.85%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.93%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.51%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	82.25%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.61%	89.34%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.30%	96.95%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Agrimonia pilosa
• Akebia quinata
• Akebia trifoliata
• Anthemis aciphylla
• Arum maculatum
• Avena sativa
• Bellis perennis
• Bothriochloa bladhii
• Calendula officinalis
• Cannabis sativa
• Capsicum annuum
• Catharanthus roseus
• Cecropia pachystachya
• Cerastium candidissimum
• Cichorium endivia
• Citrullus lanatus
• Crocus sativus
• Croton eluteria
• Daphne odora
• Daucus carota
• Dendrobium chrysanthum
• Dolomiaea souliei
• Elettaria cardamomum
• Erigeron bonariensis
• Hamamelis virginiana
• Helianthus annuus
• Ilex paraguariensis
• Inula helenium
• Laggera crispata
• Leea guineense
• Lobelia chinensis
• Lonicera japonica
• Lycium barbarum
• Lycium chinense
• Mentha arvensis
• Mentha canadensis
• Nelumbo nucifera
• Persicaria minor
• Polygala senega
• Prunus amygdalus
• Santalum spicatum
• Saussurea costus
• Scleromitrion diffusum
• Scutellaria baicalensis
• Scutellaria barbata
• Senna alexandrina
• Vachellia rigidula
• Zea mays
• Zingiber mioga

Cross-Links

• PubChem: 1549778
• NPASS: NPC66681
• LOTUS: LTS0231623
• wikiData: Q27135687