Vomifoliol, (+)-

Details

• Internal ID: dcbfd73c-ebbc-4dd1-b870-ff0270e24809
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
• InChI: InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1
• InChI Key: KPQMCAKZRXOZLB-KOIHBYQTSA-N
• Popularity: 92 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.30 g/mol
• Exact Mass: 224.14124450 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.60
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 23526-45-6
• (6S,9R)-vomifoliol
• (6S,9R)-6-hydroxy-3-oxo-alpha-ionol
• (+)-Vomifoliol
• Vomifoliol, (+)-
• (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
• CHEBI:49164
• P86438KC5J
• DTXSID601009964
• (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
• (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
• (6S,9R)-6-HYDROXY-3-OXO-.ALPHA.-IONOL
• 2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (+)-
• CHEBI:28258
• (4S)-4-hydroxy-4-((1E,3R)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one
• (4S)-4-hydroxy-4-((1E,3R)-3-hydroxybut-1-enyl)-3,5,5-trimethylcyclohex-2-en-1-one
• (4S)-4-hydroxy-4-((E,3R)-3-hydroxybut-1-enyl)-3,5,5-trimethylcyclohex-2-en-1-one
• RefChem:902052
• DTXCID101436388
• 4-hydroxy-4-((1E)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one
• 4-hydroxy-4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
• BLUMENOL A
• Roseoside aglycon
• (+/-)-Volifoliol
• (+/-)-Blumenol-A
• 50763-73-0
• B7QV234K84
• (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one
• FEMA no. 4661, (4S,3R)-(E)-(+/-)-
• 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-
• 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (4S)-
• 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-
• 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (S-(R*,S*-(E)))-
• 4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, (4S,3R)-(E)-(+/-)-
• 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-rel-
• 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-(+/-)-
• (+-)-Vomifoliol
• (+-)-Blumenol A
• Vomifoliol, (+-)-
• UNII-B7QV234K84
• UNII-P86438KC5J
• MFCD20260591
• (+)-BLUMENOL A
• CHEMBL463088
• orb1681470
• SCHEMBL1243896
• HY-N1077
• (+-)-6-hydroxy-3-oxo-alpha-ionol
• BDBM50463336
• NSC805019
• AKOS032948398
• FS-9636
• NSC-805019
• 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (+-)-
• DA-59041
• FV177947
• CS-0016364
• NS00122932
• C01760
• G14079
• Q22911785
• (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethyl-cyclohex-2-en-1-one
• (S)-4-Hydroxy-4-((R,E)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.7205	72.05%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8521	85.21%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.9208	92.08%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7565	75.65%
P-glycoprotein inhibitior	-	0.9770	97.70%
P-glycoprotein substrate	-	0.9457	94.57%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8828	88.28%
CYP3A4 inhibition	-	0.7800	78.00%
CYP2C9 inhibition	-	0.8182	81.82%
CYP2C19 inhibition	-	0.8477	84.77%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.9041	90.41%
CYP2C8 inhibition	-	0.9790	97.90%
CYP inhibitory promiscuity	-	0.8070	80.70%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7563	75.63%
Carcinogenicity (trinary)	Non-required	0.4825	48.25%
Eye corrosion	-	0.9495	94.95%
Eye irritation	-	0.5309	53.09%
Skin irritation	-	0.5268	52.68%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8533	85.33%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	+	0.8743	87.43%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.6908	69.08%
Acute Oral Toxicity (c)	III	0.7480	74.80%
Estrogen receptor binding	-	0.8585	85.85%
Androgen receptor binding	-	0.6186	61.86%
Thyroid receptor binding	-	0.6587	65.87%
Glucocorticoid receptor binding	-	0.4878	48.78%
Aromatase binding	-	0.8148	81.48%
PPAR gamma	-	0.8080	80.80%
Honey bee toxicity	-	0.9167	91.67%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9210	92.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.78%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.54%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	89.19%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.12%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.66%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	86.35%	91.49%
CHEMBL4208	P20618	Proteasome component C5	85.59%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.99%	90.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.29%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.20%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.17%	96.77%

Plants that contains it

• Acacia adunca
• Aconitum maximum
• Aconitum vilmorinianum
• Acorus calamus var. angustatus
• Actinidia kolomikta
• Adenia volkensii
• Adiantum philippense
• Albizia julibrissin
• Angelica ursina
• Annona cornifolia
• Annona glabra
• Ardisia macrocarpa
• Artemisia campestris subsp. variabilis
• Asplenium normale
• Astragalus sempervirens
• Baccharis angustifolia
• Bergera kwangsiensis
• Boronia koniambiensis
• Brassica rapa
• Brucea javanica
• Calanthe discolor
• Calostephane divaricata
• Calyptocarpus vialis
• Canarium strictum
• Cannabis sativa
• Caragana aurantiaca
• Carallia brachiata
• Carpesium macrocephalum
• Carpobrotus edulis
• Castanea crenata
• Cenchrus americanus
• Centaurea aspera
• Centrolobium tomentosum
• Ceratophyllum submersum
• Chamaecyparis pisifera
• Chenopodium album
• Chlorophytum malayense
• Chrysanthemum indicum
• Cissus rheifolia
• Clausena indica
• Coreopsis grandiflora
• Crinum firmifolium
• Crotalaria thebaica
• Croton bonplandianus
• Cynanchum bungei
• Cynara cornigera
• Dioscorea japonica
• Dipteronia dyeriana
• Dodonaea polyandra
• Dracocephalum kotschyi
• Dumortiera hirsuta
• Echeveria secunda
• Echiochilon fruticosum
• Empetrum nigrum
• Ephedra lomatolepis
• Equilabium molle
• Equisetum ramosissimum var. huegelii
• Erigeron bonariensis
• Eucalyptus globulus
• Eucalyptus melliodora
• Euchresta formosana
• Euonymus maackii
• Euphorbia clarkeana
• Galium sinaicum
• Garcinia macrophylla
• Gentiana olivieri
• Geum aleppicum
• Glechoma grandis
• Glechoma longituba
• Gnetum latifolium
• Goniothalamus malayanus
• Goupia glabra
• Gymnanthemum amygdalinum
• Gymnosporia serrata
• Hedysarum inundatum
• Helianthus annuus
• Heptapleurum divaricatum
• Houttuynia cordata
• Hymenoxys ambigens var. floribunda
• Hymenoxys hoopesii
• Hypericum laricifolium
• Inula japonica
• Ipomoea digitata
• Ipomoea nil
• Ipomoea purpurea
• Isatis tinctoria
• Jateorhiza palmata
• Lawsonia inermis
• Leonurus japonicus
• Lepisorus ussuriensis
• Lessingianthus rubricaulis
• Lindera umbellata
• Lippia carviodora
• Lysimachia mauritiana
• Macaranga tanarius
• Macrococculus pomiferus
• Magnolia stellata
• Marrubium anisodon
• Maytenus loeseneri
• Morus notabilis
• Myrica nana
• Nageia nagi
• Naucleopsis ternstroemiiflora
• Neltuma ruscifolia
• Nelumbo nucifera
• Neolitsea parvigemma
• Netrostylis capillaris
• Nicotiana gossei
• Nicotiana repanda
• Ocotea pittieri
• Odontites vulgaris
• Ongokea gore
• Ophiorrhiza blumeana
• Ophryosporus lorentzii
• Orthosiphon aristatus var. aristatus
• Pastinaca sativa
• Peltostigma guatemalense
• Peperomia heyneana
• Perrottetia multiflora
• Peucedanum palustre
• Phalaenopsis aphrodite
• Phaseolus vulgaris
• Physalis peruviana
• Physalis solanaceus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Piper kadsura
• Podocarpus salignus
• Premna odorata
• Prunus armeniaca
• Prunus padus
• Pseudocydonia sinensis
• Psilostrophe cooperi
• Psychotria bahiensis
• Pterocaulon polystachyum
• Pterocaulon rugosum
• Pyracantha coccinea
• Rauvolfia tetraphylla
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia chinensis
• Salvia prionitis
• Salvia syriaca
• Salvia willeana
• Satureja montana
• Saussurea cordifolia
• Saussurea triangulata
• Schistostephium rotundifolium
• Scutellaria amoena
• Senecio grandiflorus
• Sesbania drummondii
• Sida acuta
• Sideritis syriaca
• Sideritis tragoriganum
• Siphocampylus verticillatus
• Solanum jamaicense
• Solanum laxum
• Solanum lyratum
• Spatholobus suberectus
• Stachys byzantina
• Staphylea japonica
• Stephania succifera
• Stevia salicifolia
• Swertia franchetiana
• Tabebuia angustata
• Taxus mairei
• Tetragonotheca ludoviciana
• Teucrium alyssifolium
• Thuja plicata
• Tithonia rotundifolia
• Trichosanthes kirilowii
• Tridax procumbens
• Trifolium alexandrinum
• Typha latifolia
• Urolepis hecatantha
• Vaccinium oxycoccos
• Vepris glomerata var. glomerata
• Veratrum shanense
• Vernonanthura serratuloides
• Viburnum chingii
• Viguiera incana
• Viscum album
• Viscum coloratum
• Vitis vinifera
• Wikstroemia retusa
• Xanthium strumarium
• Zanthoxylum melanostictum
• Zanthoxylum tetraspermum
• Zephyranthes carinata
• Ziziphus jujuba

Cross-Links

• PubChem: 5280462
• NPASS: NPC201562
• ChEMBL: CHEMBL463088
• LOTUS: LTS0052786
• wikiData: Q22911785