alpha-PINENE

Details

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Internal ID dc196213-a0bd-41fd-b7f5-fba96d767f29
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
IUPAC Name 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
SMILES (Canonical) CC1=CCC2CC1C2(C)C
SMILES (Isomeric) CC1=CCC2CC1C2(C)C
InChI InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3
InChI Key GRWFGVWFFZKLTI-UHFFFAOYSA-N
Popularity 5,878 references in papers

Physical and Chemical Properties

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Molecular Formula C10H16
Molecular Weight 136.23 g/mol
Exact Mass 136.125200510 g/mol
Topological Polar Surface Area (TPSA) 0.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 3.00
H-Bond Acceptor 0
H-Bond Donor 0
Rotatable Bonds 0

Synonyms

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80-56-8
2-Pinene
Acintene A
.alpha.-Pinene
Pinene isomer
2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
pin-2(3)-ene
alfa-Pinene
Sylvapine A
PINENE, ALPHA
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of alpha-PINENE

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9941 99.41%
Caco-2 + 0.6490 64.90%
Blood Brain Barrier + 0.9500 95.00%
Human oral bioavailability + 0.8286 82.86%
Subcellular localzation Lysosomes 0.6933 69.33%
OATP2B1 inhibitior - 0.8597 85.97%
OATP1B1 inhibitior + 0.9538 95.38%
OATP1B3 inhibitior + 0.9024 90.24%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.9140 91.40%
P-glycoprotein inhibitior - 0.9749 97.49%
P-glycoprotein substrate - 0.9284 92.84%
CYP3A4 substrate - 0.5864 58.64%
CYP2C9 substrate - 0.8062 80.62%
CYP2D6 substrate - 0.7846 78.46%
CYP3A4 inhibition - 0.8558 85.58%
CYP2C9 inhibition - 0.7584 75.84%
CYP2C19 inhibition - 0.6577 65.77%
CYP2D6 inhibition - 0.8950 89.50%
CYP1A2 inhibition - 0.8844 88.44%
CYP2C8 inhibition - 0.9590 95.90%
CYP inhibitory promiscuity - 0.5287 52.87%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.5700 57.00%
Carcinogenicity (trinary) Non-required 0.4741 47.41%
Eye corrosion - 0.8107 81.07%
Eye irritation + 0.9629 96.29%
Skin irritation + 0.5781 57.81%
Skin corrosion - 0.9041 90.41%
Ames mutagenesis - 0.9800 98.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5110 51.10%
Micronuclear - 0.9641 96.41%
Hepatotoxicity + 0.7125 71.25%
skin sensitisation + 0.8521 85.21%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.5333 53.33%
Mitochondrial toxicity - 0.5437 54.37%
Nephrotoxicity - 0.7361 73.61%
Acute Oral Toxicity (c) III 0.8258 82.58%
Estrogen receptor binding - 0.9178 91.78%
Androgen receptor binding - 0.8454 84.54%
Thyroid receptor binding - 0.8973 89.73%
Glucocorticoid receptor binding - 0.8895 88.95%
Aromatase binding - 0.9220 92.20%
PPAR gamma - 0.8581 85.81%
Honey bee toxicity - 0.8532 85.32%
Biodegradation + 0.8000 80.00%
Crustacea aquatic toxicity + 0.7900 79.00%
Fish aquatic toxicity + 0.9936 99.36%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4040 P28482 MAP kinase ERK2 39810.7 nM
Potency
via CMAUP
CHEMBL1963 P16473 Thyroid stimulating hormone receptor 6309.6 nM
6309.6 nM
Potency
Potency
via CMAUP
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.36% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.67% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.52% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 84.35% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.55% 97.25%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Abies alba
Abies balsamea
Abies cilicica
Abies magnifica
Abies sachalinensis
Abies sibirica
Abies sibirica subsp. semenovii
Acacia nuperrima
Achillea abrotanoides
Achillea asiatica
Achillea collina
Achillea erba-rotta
Achillea fragrantissima
Achillea grandifolia
Achillea millefolium
Achillea ptarmica subsp. ptarmica
Achillea santolinoides
Achyrospermum africanum
Acokanthera oblongifolia
Acorus calamus
Acorus calamus var. angustatus
Acorus gramineus
Actaea japonica
Actinidia chinensis
Actinodium cunninghamii
Aegle marmelos
Aesculus hippocastanum
Aframomum angustifolium
Aframomum melegueta
Agastache foeniculum
Agastache rugosa
Agathosma betulina
Ageratum conyzoides
Ajania fastigiata
Ajuga chamaepitys
Akebia quinata
Akebia trifoliata
Allium chinense
Allium macrostemon
Aloysia citrodora
Aloysia gratissima
Alpinia breviligulata
Alpinia carinata
Alpinia chinensis
Alpinia conchigera
Alpinia galanga
Alpinia latilabris
Alpinia oxyphylla
Alpinia zerumbet
Ambrosia artemisiifolia
Ammodaucus leucotrichus
Anemopsis californica
Anethum graveolens
Angelica acutiloba
Angelica archangelica
Angelica gigas
Angelica sinensis
Annona cascarilloides
Annona glabra
Annona muricata
Annona reticulata
Annona squamosa
Anthemis aciphylla
Anthemis cotula
Apium graveolens
Araucaria cunninghamii
Artemisia absinthium
Artemisia afra
Artemisia annua
Artemisia argyi
Artemisia austriaca
Artemisia campestris subsp. campestris
Artemisia capillaris
Artemisia carvifolia
Artemisia dracunculus
Artemisia halophila
Artemisia jacutica
Artemisia judaica
Artemisia lagocephala
Artemisia lagopus
Artemisia macrocephala
Artemisia montana
Artemisia princeps
Artemisia rubripes
Artemisia salsoloides
Artemisia scoparia
Artemisia sericea
Artemisia thuscula
Artemisia tridentata
Artemisia vulgaris
Artemisia xerophytica
Arum maculatum
Asarum asperum
Asarum canadense
Asarum europaeum
Asarum fauriei
Asarum heterotropoides
Asarum megacalyx
Asarum nipponicum var. nankaiense
Asarum sieboldii
Asarum simile
Aspilia africana
Atalantia buxifolia
Athamanta macedonica
Atherosperma moschatum
Atractylodes lancea
Aucklandia costus
Aucoumea klaineana
Austrobaileya scandens
Averrhoa carambola
Azadirachta indica
Baccharis alaternoides
Baccharis articulata
Baccharis dracunculifolia
Baccharis uncinella
Backhousia angustifolia
Badilloa steetzii
Baeckea frutescens
Bazzania japonica
Bellis perennis
Betula alnoides
Bidens bipinnata
Blepharocalyx salicifolius
Blumea lacera
Boronia latipinna
Boswellia sacra
Boswellia serrata
Bothriochloa bladhii
Brassica napus
Bupleurum chinense
Bupleurum falcatum
Bupleurum fruticescens
Bupleurum fruticosum
Bupleurum gibraltaricum
Bupleurum rigidum
Bupleurum scorzonerifolium
Caesulia axillaris
Callicarpa americana
Calycanthus floridus
Calycolpus warszewiczianus
Camellia sinensis
Cananga odorata
Canarium luzonicum
Canella winterana
Cannabis sativa
Cantinoa mutabilis
Capillipedium parviflorum
Capsicum annuum
Carapichea ipecacuanha
Carum carvi
Casimiroa greggii
Cassinia quinquefaria
Catha edulis
Catharanthus roseus
Cedrus libani
Centella asiatica
Centratherum punctatum
Chaerophyllum bulbosum
Chaerophyllum macrospermum
Chamaecyparis formosensis
Chamaecyparis lawsoniana
Chamaecyparis obtusa
Chamaecyparis pisifera
Chamaemelum nobile
Chiliadenus lopadusanus
Chromolaena odorata
Chrysanthemum indicum
Chrysopogon zizanioides
Cinnamomum aromaticum
Cinnamomum impressinervium
Cinnamomum oliveri
Cinnamomum sieboldii
Cinnamomum tamala
Cinnamomum verum
Cistus clusii
Cistus creticus
Cistus monspeliensis
Citrus × aurantium
Citrus deliciosa
Citrus japonica
Citrus maxima
Citrus medica
Citrus trifoliata
Cleistopholis patens
Cleonia lusitanica
Clinopodium brownei
Clinopodium gilliesii
Clinopodium grandiflorum
Clinopodium menthifolium subsp. menthifolium
Clinopodium nepeta subsp. spruneri
Clinopodium pamphylicum
Clinopodium serpyllifolium subsp. fruticosum
Clinopodium suaveolens
Cnidium monnieri
Coespeletia timotensis
Commiphora africana
Commiphora gurreh
Condea verticillata
Conioselinum anthriscoides
Coriandrum sativum
Cota tinctoria
Cotinus coggygria
Cratoxylum cochinchinense
Crocus sativus
Croton adenocalyx
Croton eluteria
Croton flavens
Croton glandulosus
Croton lachnostachyus
Croton malambo
Croton nepetifolius
Croton sonderianus
Croton stelluliferus
Cryptocarya agathophylla
Cryptomeria japonica
Cryptotaenia japonica
Cuminum cyminum
Cunila microcephala
Cupressus nootkatensis
Cupressus sempervirens
Curcuma kwangsiensis
Curcuma longa
Curcuma mangga
Curcuma phaeocaulis
Curcuma pierreana
Curcuma trichosantha
Curcuma wenyujin
Curcuma zedoaria
Curio talinoides
Cymbopogon citratus
Cymbopogon distans
Cymbopogon flexuosus
Cyperus rotundus
Dacrydium nidulum
Dacryodes excelsa
Darwinia citriodora
Daucus carota
Diplotaenia cachrydifolia
Ducrosia anethifolia
Ducrosia ismaelis
Echinacea purpurea
Echinophora orientalis
Echinophora tenuifolia
Echinophora tenuifolia subsp. sibthorpiana
Ekimia bornmuelleri
Ekimia petrophila
Elettaria cardamomum
Eleutherococcus giraldii
Elsholtzia blanda
Elsholtzia ciliata
Elsholtzia fruticosa
Elsholtzia pilosa
Elwendia persica
Entandrophragma cylindricum
Enydra fluctuans
Erigeron canadensis
Erigeron philadelphicus
Eryngium foetidum
Espeletia weddellii
Espeletiopsis guacharaca
Etlingera elatior
Eucalyptus apodophylla
Eucalyptus brassiana
Eucalyptus bridgesiana
Eucalyptus camaldulensis
Eucalyptus campanulata
Eucalyptus cloeziana
Eucalyptus crenulata
Eucalyptus dealbata
Eucalyptus deglupta
Eucalyptus delegatensis
Eucalyptus diversicolor
Eucalyptus forrestiana
Eucalyptus globulus
Eucalyptus jensenii
Eucalyptus leucoxylon
Eucalyptus loxophleba
Eucalyptus nitens
Eucalyptus nova-anglica
Eucalyptus pulverulenta
Eucalyptus radiata
Eucalyptus staigeriana
Eucalyptus stenostoma
Eucalyptus tereticornis
Eugenia zuchowskiae
Eupatorium cannabinum
Eupatorium capillifolium
Ferula assa-foetida
Ferula flabelliloba
Ferula fukanensis
Ferula gummosa
Ferula ovina
Ferulago nodosa
Ferulago thirkeana
Ferulago trachycarpa
Ficus carica
Foeniculum vulgare
Forsythia suspensa
Forsythia viridissima
Frullania monocera
Gackstroemia magellanica
Glaucosciadium cordifolium
Glebionis coronaria
Glehnia littoralis
Gossypium hirsutum
Gossypium sturtianum
Grindelia hirsutula
Gutierrezia sarothrae
Halocarpus bidwillii
Hansenia forbesii
Hansenia weberbaueriana
Haplophyllum tuberculatum
Hartwrightia floridana
Hedychium coronarium
Hedyosmum mexicanum
Helichrysum ambiguum
Helichrysum bracteiferum
Helichrysum odoratissimum
Helichrysum stoechas
Heracleum dissectum
Heracleum persicum
Hesperis matronalis
Hesperozygis rhododon
Heteranthemis viscidi-hirta
Heteropyxis natalensis
Homalomena occulta
Houttuynia cordata
Humulus lupulus
Hydrocotyle sibthorpioides
Hymenocrater incanus
Hypericum androsaemum
Hypericum heterophyllum
Hypericum hircinum
Hypericum perfoliatum
Hypericum perforatum
Hypericum rumeliacum
Hypericum triquetrifolium
Hyptis emoryi
Hyptis spicigera
Hyptis suaveolens
Hyssopus officinalis
Hyssopus officinalis subsp. aristatus
Hyssopus seravschanicus
Ichthyothere connata
Illicium difengpi
Illicium verum
Inula helenium
Inula racemosa
Isodon melissoides
Juglans nigra
Jungermannia truncata
Jungermannia vulcanicola
Juniperus communis
Juniperus drupacea
Juniperus excelsa
Juniperus foetidissima
Juniperus jaliscana
Juniperus monticola
Juniperus oxycedrus
Keteleeria davidiana
Kippistia suaedifolia
Kunzea salina
Kunzea sinclairii
Laggera crispata
Lagoecia cuminoides
Lantana camara
Lantana ukambensis
Lanxangia tsaoko
Larix gmelinii var. gmelinii
Larix gmelinii var. olgensis
Larix kaempferi
Larix occidentalis
Larix sibirica
Laser trilobum
Laurus nobilis
Lavandula angustifolia
Lavandula angustifolia subsp. angustifolia
Lavandula latifolia
Lavandula stoechas
Lavandula stoechas subsp. luisieri
Leonotis leonurus
Leonurus japonicus
Lepechinia chamaedryoides
Lepechinia floribunda
Leptospermum scoparium
Levisticum officinale
Ligularia vellerea
Ligusticum filicinum
Ligusticum officinale
Ligusticum porteri
Ligusticum scoticum
Ligusticum striatum
Lindera aggregata
Lindera neesiana
Lippia kituiensis
Lippia multiflora
Liquidambar orientalis
Liquidambar styraciflua
Liriodendron tulipifera
Litchi chinensis
Litsea cubeba
Litsea glaucescens
Lobelia chinensis
Machilus japonica
Machilus thunbergii
Magnolia balansae
Magnolia biondii
Magnolia denudata
Magnolia kobus
Magnolia obovata
Magnolia officinalis
Magnolia salicifolia
Magnolia sprengeri
Malus domestica
Mangifera indica
Marsupella emarginata
Melaleuca alternifolia
Melaleuca linariifolia
Melaleuca quinquenervia
Melaleuca squarrosa
Melaleuca triumphalis
Mentha × piperita
Mentha × verticillata
Mentha aquatica
Mentha arvensis
Mentha canadensis
Mentha pulegium
Mentha spicata
Mentha suaveolens
Micromeria biflora
Micromeria maderensis
Micromeria myrtifolia
Micromyrtus striata
Mikania cordifolia
Mikania hookeriana
Minthostachys andina
Minthostachys glabrescens
Minthostachys mollis
Molopospermum peloponnesiacum
Monanthotaxis capea
Monarda citriodora
Monarda fistulosa
Montanoa tomentosa
Mosla cavaleriei
Mosla chinensis
Murraya exotica
Murraya paniculata
Myrcianthes cisplatensis
Myrcianthes fragrans
Myrciaria floribunda
Myristica fragrans
Myrrhis odorata
Myrtus communis
Narcissus tazetta
Nectandra angustifolia
Nelumbo lutea
Nepeta annua
Nepeta crispa
Nepeta glomerulosa
Nepeta nuda
Nepeta racemosa
Nepeta trachonitica
Nepeta viscida
Nicotiana bonariensis
Nigella sativa
Ocimum americanum
Ocimum basilicum
Ocimum campechianum
Ocimum gratissimum
Ocimum gratissimum subsp. gratissimum
Ocimum kilimandscharicum
Ocimum tenuiflorum
Oenanthe aquatica
Olearia phlogopappa
Ophryosporus charua
Ophrys × arachnitiformis
Origanum acutidens
Origanum cordifolium
Origanum dictamnus
Origanum hypericifolium
Origanum laevigatum
Origanum majorana
Origanum minutiflorum
Origanum onites
Origanum sipyleum
Origanum syriacum
Origanum vulgare
Origanum vulgare subsp. gracile
Osbornia octodonta
Osmitopsis asteriscoides
Panax ginseng
Panax notoginseng
Panax quinquefolius
Parthenium argentatum
Parthenium confertum
Pelargonium citronellum
Pelargonium endlicherianum
Pelargonium graveolens
Pelargonium quercifolium
Pelargonium vitifolium
Perilla frutescens
Persea americana
Persicaria minor
Peucedanum oreoselinum
Peucedanum zenkeri
Phlomis fruticosa
Phlomis lanata
Picea abies
Picea glehnii
Picea koraiensis
Picea orientalis
Picea rubens
Picea schrenkiana
Pilocarpus jaborandi
Pimenta racemosa
Pimpinella anisum
Pimpinella serbica
Pinus brutia var. pityusa
Pinus caribaea
Pinus cembra
Pinus cembroides
Pinus contorta
Pinus densiflora
Pinus elliottii var. densa
Pinus flexilis
Pinus heldreichii
Pinus longaeva
Pinus massoniana
Pinus merkusii
Pinus monticola
Pinus oocarpa
Pinus palustris
Pinus ponderosa
Pinus pumila
Pinus radiata
Pinus sylvestris
Pinus taeda
Pinus thunbergii
Piper auritum
Piper betle
Piper cernuum
Piper corcovadense
Piper cubeba
Piper fimbriulatum
Piper gaudichaudianum
Piper gibbilimbum
Piper guineense
Piper marginatum
Piper nigrum
Piper regnellii
Piper sylvestre
Pistacia atlantica
Pistacia lentiscus
Pistacia vera
Pittosporum balfourii
Pittosporum tobira
Pittosporum undulatum
Platycladus orientalis
Plumeria rubra
Poliomintha incana
Polygala senega
Polygonatum odoratum
Porophyllum gracile
Porophyllum ruderale
Prangos uechtritzii
Prangos uloptera
Protium heptaphyllum
Pseudotsuga menziesii
Psiadia altissima
Psidium guajava
Psidium guineense
Psidium salutare
Pteronia incana
Ptychopetalum olacoides
Pueraria montana var. lobata
Punica granatum
Pycnanthemum floridanum
Quercus ilex
Radula perrottetii
Rhanterium epapposum
Rhodiola rosea
Rhododendron dauricum
Rhododendron ferrugineum
Rhododendron mucronulatum
Robinia pseudoacacia
Rosa gallica
Rosmarinus officinalis
Saccogyna viticulosa
Salvia absconditiflora
Salvia aurea
Salvia caespitosa
Salvia cuspidata subsp. gilliesii
Salvia dorisiana
Salvia fruticosa
Salvia hydrangea
Salvia mellifera
Salvia officinalis
Salvia sahendica
Salvia sclarea
Santiria trimera
Santolina canescens
Santolina chamaecyparissus
Santolina insularis
Santolina neapolitana
Santolina rosmarinifolia
Sassafras albidum
Satureja cuneifolia
Satureja hortensis
Satureja montana
Satureja spicigera
Satureja subspicata subsp. liburnica
Satureja thymbra
Satureja wiedemanniana
Saxifraga stolonifera
Scalesia crockeri
Scandix australis
Schinus latifolius
Schinus molle
Schisandra chinensis
Scleromitrion diffusum
Senecio scandens
Senecio subrubriflorus
Senna alexandrina
Sequoia sempervirens
Sequoiadendron giganteum
Seriphidium herba-alba
Seseli farrenyi
Sideritis brevidens
Sideritis congesta
Sideritis dichotoma
Sideritis hispida
Sideritis leucantha
Sideritis lyciae
Sideritis montana
Sideritis perfoliata
Sideritis perfoliata subsp. athoa
Sideritis pungens
Sideritis raeseri
Sideritis tragoriganum
Sium latifolium
Smallanthus fruticosus
Smyrnium perfoliatum
Solanecio biafrae
Solanum tuberosum
Solidago canadensis
Solidago gigantea
Solidago litoralis
Solidago nemoralis
Solidago odora
Sphagneticola trilobata
Stachys atherocalyx
Stachys balansae
Stachys glutinosa
Stachys obliqua
Steganotaenia araliacea
Stevia rebaudiana
Symphyotrichum subulatum
Syzygium aromaticum
Syzygium cumini
Syzygium nervosum
Syzygium samarangense
Tagetes minuta
Tamarindus indica
Tambourissa leptophylla
Tanacetum annuum
Tanacetum millefolium
Tanacetum parthenium
Tanacetum vulgare
Targionia hypophylla
Taxodium distichum
Tessaria fastigiata
Tetradium ruticarpum
Teucrium melissoides
Teucrium micropodioides
Teucrium montanum
Teucrium polium
Teucrium scorodonia
Thapsia maxima
Thryptomene saxicola
Thuja occidentalis
Thuja plicata
Thujopsis dolabrata
Thymbra capitata
Thymbra spicata
Thymus × citriodorus
Thymus baeticus
Thymus broussonetii
Thymus camphoratus
Thymus cariensis
Thymus cilicicus
Thymus eigii
Thymus funkii
Thymus karamarianicus
Thymus kotschyanus
Thymus longicaulis
Thymus membranaceus
Thymus nummularius
Thymus pastoralis
Thymus piperella
Thymus pubescens
Thymus quinquecostatus
Thymus revolutus
Thymus riatarum
Thymus saturejoides
Thymus sibthorpii
Thymus sipyleus
Thymus thracicus
Thymus vulgaris
Thymus willkommii
Thymus zygioides
Thymus zygis
Tilesia baccata
Tithonia diversifolia
Toddalia asiatica
Torilis japonica
Trachyspermum ammi
Trichocolea tomentella
Trichostema dichotomum
Umbellularia californica
Uvaria chamae
Vaccinium vitis-idaea
Valeriana jatamansi
Valeriana officinalis
Valeriana wolgensis
Varronia curassavica
Verbesina persicifolia
Virola surinamensis
Vitex agnus-castus
Vitex limonifolia
Vitex negundo
Vitex trifolia
Vitis vinifera
Wurfbainia compacta
Wurfbainia longiligularis
Wurfbainia villosa
Wurfbainia villosa var. xanthioides
Xenophyllum poposum
Xeranthemum annuum
Xylopia aethiopica
Xylopia aromatica
Xylopia parviflora
Xylopia sericea
Zanthoxylum bungeanum
Zanthoxylum gilletii
Zanthoxylum schinifolium
Zanthoxylum simulans
Zanthoxylum zanthoxyloides
Zea mays
Zieria smithii
Zingiber mioga
Zingiber officinale
Zingiber zerumbet

Cross-Links

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PubChem 6654
NPASS NPC13991
ChEMBL CHEMBL442565
LOTUS LTS0132416
wikiData Q27104380