(-)-beta-Pinene

Details

• Internal ID: 32341c39-f52a-4c87-8f5b-6d7cf0f51dbe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
• InChI: InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1
• InChI Key: WTARULDDTDQWMU-IUCAKERBSA-N
• Popularity: 409 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23 g/mol
• Exact Mass: 136.125200510 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 18172-67-3
• (-)-nopinene
• Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-, (1S,5S)-
• (1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane
• AFN153A7SU
• (-)-(1S,5S)-beta-pinene
• DTXSID1041184
• CHEBI:28359
• (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
• DTXCID9021184
• FEMA NO. 2903, (-)-
• Bicyclo(3.1.1)heptane, 6,6-dimethyl-2-methylene-, (1S,5S)-
• (1S,5S)-6,6-DIMETHYL-2-METHYLENEBICYCLO(3.1.1)HEPTANE
• (1S,5S)-6,6-dimethyl-2-methylidenebicyclo(3.1.1)heptane
• I2-Pinene, (-)-
• RefChem:1049087
• 242-060-2
• (-)-b-Pinene
• (-)-Pin-2(10)-ene
• (1S)-(-)-beta-Pinene
• (-)-2(10)-Pinene
• (1S,5S)-pin-2(10)-ene
• (S)-b-Pinene
• MFCD00001345
• (1S,5S)-6,6-dimethyl-2-methylene-norpinane
• l-beta-Pinene
• (1S)-(1)-beta-Pinene
• Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-, (1S)-
• (1S)-(-)-.beta.-Pinene
• UNII-AFN153A7SU
• (1S,5S)-2(10)-Pinene
• Bicyclo(3.1.1)heptane, 6,6-dimethyl-2-methylene-, (1S)-
• CCRIS 3201
• Laevo-b-pinene
• NSC-21447
• NSC-59190
• NSC-406265
• (s)-beta-pinene
• L-b-Pinene
• (-)-beta-piene
• EINECS 242-060-2
• (1S)-beta-Pinene
• beta-Pinene: Nopinene
• beta-Pinene (natural)
• (-)- beta -Pinene
• beta-Pinene, (-)-
• (?)-|A-Pinene
• (1S,5S)-beta-pinene
• UNII-4MS8VHZ1HJ
• BETA-PINENE [FCC]
• EC 242-060-2
• BETA-PINENE [HSDB]
• (-)-beta-Pinene, 99%
• .BETA.-PINENE, L-
• 1S,5S-(-)-beta-Pinene
• (1S)-6,6-DIMETHYL-2-METHYLENEBICYCLO(3.1.1)HEPTANE
• orb105274
• .BETA.-PINENE [MI]
• (1S)-(-)-?-Pinene
• .BETA.-PINENE [FHFI]
• .BETA.-PINENE-(-)
• (1S)-.BETA.-PINENE
• SCHEMBL1636093
• (-)-beta-Pinene, >=99%
• CHEMBL3184774
• HSDB 5615
• HY-N0550R
• (+/-)-.BETA.-PINENE
• 6,6-Dimethyl-2-methylenenorpinane
• HY-N0550
• (1S)-(-)-.BETA-PINENE
• EINECS 204-872-5
• EINECS 245-424-9
• Tox21_301162
• MSK005057
• NSC 21447
• PC-600
• .BETA.-PINENE, (+/-)-
• (-)-(1S)-.BETA.-PINENE
• (-)-beta-Pinene, analytical standard
• (1S)-(-)-pin-2(10)-ene
• AKOS006342971
• LMPR0102120013
• NCGC00248311-01
• NCGC00255060-01
• (-)-(1S,5S)-.BETA.-PINENE
• (-)-beta-Pinene, >=97%, FCC, FG
• (1S,5S)-6,6-Dimethyl-2-methylenebicyclo
• AI3-24483
• CAS-18172-67-3
• 2,2,6-Trimethylbicyclo(3.1.1)hept-2-ene
• CS-0009078
• NS00094639
• S6275
• C06307
• E79173
• EN300-303399
• (1S)-beta-Pinene 2000 microg/mL in Acetonitrile
• (1)-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptane
• Q27103655
• Z1201618602
• (-)-beta-Pinene, primary pharmaceutical reference standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.7184	71.84%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Lysosomes	0.7266	72.66%
OATP2B1 inhibitior	-	0.8485	84.85%
OATP1B1 inhibitior	+	0.9218	92.18%
OATP1B3 inhibitior	+	0.8860	88.60%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9400	94.00%
P-glycoprotein inhibitior	-	0.9757	97.57%
P-glycoprotein substrate	-	0.9377	93.77%
CYP3A4 substrate	-	0.5512	55.12%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.7846	78.46%
CYP3A4 inhibition	-	0.8825	88.25%
CYP2C9 inhibition	-	0.7500	75.00%
CYP2C19 inhibition	-	0.6602	66.02%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.8077	80.77%
CYP2C8 inhibition	-	0.9329	93.29%
CYP inhibitory promiscuity	-	0.7244	72.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.4761	47.61%
Eye corrosion	-	0.8151	81.51%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.5655	56.55%
Skin corrosion	-	0.9730	97.30%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5596	55.96%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	+	0.8274	82.74%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.6164	61.64%
Nephrotoxicity	-	0.6858	68.58%
Acute Oral Toxicity (c)	III	0.8344	83.44%
Estrogen receptor binding	-	0.9073	90.73%
Androgen receptor binding	-	0.7446	74.46%
Thyroid receptor binding	-	0.8613	86.13%
Glucocorticoid receptor binding	-	0.7551	75.51%
Aromatase binding	-	0.8957	89.57%
PPAR gamma	-	0.8782	87.82%
Honey bee toxicity	-	0.7907	79.07%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	+	0.9600	96.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.95%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.13%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.01%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.84%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.56%	90.17%
CHEMBL1871	P10275	Androgen Receptor	80.19%	96.43%

Plants that contains it

• Abies alba
• Abies magnifica
• Acer saccharum
• Achillea clypeolata
• Achillea millefolium
• Acokanthera oblongifolia
• Acorus calamus
• Acorus gramineus
• Adina trichotoma
• Afraegle paniculata
• Aframomum melegueta
• Agastache rugosa
• Agrimonia eupatoria
• Aizoon africanum
• Alangium premnifolium
• Alcea rosea
• Aloysia citrodora
• Alpinia flabellata
• Alpinia galanga
• Alpinia oxyphylla
• Alpinia roxburghii
• Ammodendron karelinii
• Anacyclus pyrethrum
• Angelica japonica
• Angelica sinensis
• Angelica tarokoensis
• Anthemis aciphylla
• Artemisia annua
• Artemisia argyi
• Artemisia scoparia
• Artemisia vulgaris
• Artemisia xerophytica
• Aster tataricus
• Asterolasia squamuligera
• Astragalus glycyphyllos
• Athanasia crithmifolia
• Athrixia elata
• Azadirachta indica
• Baccharis truncata
• Balanops australiana
• Benincasa hispida
• Berberis julianae
• Bidens andicola
• Blumea viscosa
• Bombax ceiba
• Brachylaena perrieri
• Bridelia ferruginea
• Buglossoides arvensis
• Bunium paucifolium
• Bystropogon origanifolius
• Callitropsis nootkatensis
• Capillipedium parviflorum
• Cardamine heptaphylla
• Carum carvi
• Cassinia subtropica
• Catha edulis
• Catharanthus roseus
• Cedrus libani
• Centaurea benedicta
• Centaurea cheiranthifolia
• Centella asiatica
• Cerbera odollam
• Chloranthus fortunei
• Chrysanthemum indicum
• Chuquiraga erinacea
• Cinnamomum chekiangense
• Cistus clusii
• Cistus creticus
• Citrus × aurantium
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Cladanthus arabicus
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Colchicum arenarium
• Condea verticillata
• Conioselinum anthriscoides
• Conioselinum officinale
• Coriandrum sativum
• Cornus officinalis
• Crateva magna
• Cratoxylum formosum subsp. pruniflorum
• Crinum jagus
• Croton malambo
• Cuphea hyssopifolia
• Cuscuta australis
• Cylindrolobus mucronatus
• Cyperus rotundus
• Daphnandra johnsonii
• Daucus carota
• Davallia perdurans
• Descurainia sophia
• Dianella revoluta
• Diospyros ferrea
• Diospyros verrucosa
• Diplotropis ferruginea
• Elettaria cardamomum
• Epimedium davidii
• Erysimum odoratum
• Erythrina burttii
• Espeletia timotensis
• Eucalyptus viminalis
• Euonymus nanoides
• Euonymus tingens
• Euphorbia cornigera
• Euphorbia palustris
• Euphorbia pithyusa
• Euphrasia regelii
• Farfugium japonicum
• Foeniculum vulgare
• Fouquieria diguetii
• Fritillaria monantha
• Frullania tamarisci
• Globba variabilis
• Grazielia serrata
• Gyrothyra underwoodiana
• Hesperis matronalis
• Heterotheca inuloides
• Hippeastrum aulicum
• Holarrhena floribunda
• Homalomena occulta
• Hortonia angustifolia
• Houttuynia cordata
• Hylocomium splendens
• Hyssopus officinalis
• Ilex amara
• Illicium difengpi
• Isodon japonicus
• Jacobaea argunensis
• Jacobaea subalpina
• Julbernardia globiflora
• Juniperus communis
• Keteleeria davidiana
• Kippistia suaedifolia
• Knightia excelsa
• Kokoona ochracea
• Kokoona reflexa
• Laggera crispata
• Lamprolobium fruticosum
• Lantana camara
• Larix sibirica
• Lasiosiphon lampranthus
• Lathyrus latifolius
• Laurus nobilis
• Lavandula angustifolia
• Leonurus glaucescens
• Lepidium draba
• Leptospermum scoparium
• Ligularia hodgsonii
• Lindera aggregata
• Machilus japonica
• Machilus obovatifolia
• Machilus thunbergii
• Maesa ramentacea
• Magnolia obovata
• Marsupella emarginata
• Medicosma fareana
• Melaleuca alternifolia
• Mentha × piperita
• Mentha aquatica
• Mentha longifolia subsp. longifolia
• Mentha pulegium
• Mentha suaveolens
• Micromeria pineolens
• Mikania grazielae
• Miliusa balansae
• Millettia laurentii
• Mimusops laurifolia
• Molopospermum peloponnesiacum
• Monodora tenuifolia
• Moringa oleifera
• Mosla chinensis
• Myristica fragrans
• Myrrhis odorata
• Nepeta multifida
• Nicotiana bonariensis
• Ocimum tenuiflorum
• Oenanthe aquatica
• Ononis viscosa
• Ophryosporus charua
• Oreocome striata
• Othonna macrophylla
• Paragynoxys meridana
• Pedicularis rex
• Pentachondra pumila
• Phagnalon rupestre
• Phlomoides ostrowskiana
• Phlox paniculata
• Picea abies
• Picea rubens
• Piliostigma thonningii
• Pimpinella peregrina
• Pinus cembra
• Pinus edulis
• Pinus heldreichii
• Pinus lambertiana
• Pinus monticola
• Pinus palustris
• Pinus pumila
• Pinus strobus
• Pinus sylvestris
• Pinus wallichiana
• Piper aduncum
• Piper arboreum
• Piper callosum
• Pistacia atlantica
• Pittocaulon bombycophole
• Platycladus orientalis
• Pleodendron costaricense
• Pleogyne australis
• Pluchea dioscoridis
• Pluchea odorata
• Pogostemon cablin
• Polyachyrus sphaerocephalus
• Polygala amara
• Posidonia oceanica
• Prioria pinnata
• Pseudotsuga menziesii
• Pterocarpus erinaceus
• Pyrola decorata
• Pyrola rotundifolia
• Pyrus bourgaeana
• Quercus petraea subsp. petraea
• Quercus serrata
• Rhodiola rosea
• Rubus allegheniensis
• Rubus pungens
• Salacia lehmbachii
• Salacia madagascariensis
• Salix petiolaris
• Salvia abrotanoides
• Salvia barrelieri
• Salvia broussonetii
• Salvia lanigera
• Salvia officinalis
• Salvia pisidica
• Salvia sclarea
• Salvia yosgadensis
• Sandea japonica
• Sandoricum koetjape
• Sanguisorba minor
• Santiria trimera
• Santolina chamaecyparissus
• Saussurea lyrata
• Scutellaria baicalensis
• Sedum sarmentosum
• Sideritis brevibracteata
• Sideritis chamaedryfolia
• Sideritis lanata
• Sideroxylon cubense
• Sium latifolium
• Solanum acaule
• Solanum crinitum
• Solidago canadensis
• Stephania sutchuenensis
• Stevia alpina
• Strychnos tomentosa
• Styrax
• Suaeda maritima
• Swertia delavayi
• Swertia japonica
• Syzygium cumini
• Tamarix gallica
• Tanacetum annuum
• Tanacetum vulgare
• Tetraneuris acaulis
• Thymus camphoratus
• Thymus piperella
• Torminalis glaberrima
• Triunia erythrocarpa
• Tubocapsicum anomalum
• Uncaria longiflora
• Unonopsis glaucopetala
• Ursinia speciosa
• Vaccinium vitis-idaea
• Valeriana officinalis
• Vepris hiernii
• Viguiera decurrens
• Viola hondoensis
• Vismia jefensis
• Vitex agnus-castus
• Walsura pinnata
• Wurfbainia neoaurantiaca
• Zanthoxylum schinifolium
• Zieria smithii
• Zingiber officinale

Cross-Links

• PubChem: 440967
• NPASS: NPC62086
• LOTUS: LTS0108757
• wikiData: Q27103655