Bornyl acetate, (-)-

Details

• Internal ID: 83ffdf5f-bd42-4289-9b42-0852650ef8fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
• SMILES (Canonical): CC(=O)OC1CC2CCC1(C2(C)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2CC[C@]1(C2(C)C)C
• InChI: InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12+/m0/s1
• InChI Key: KGEKLUUHTZCSIP-HOSYDEDBSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29 g/mol
• Exact Mass: 196.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.76
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 5655-61-8
• BORNYL ACETATE
• L-bornyl acetate
• borneol acetate
• 76-49-3
• (-)-Borneol acetate
• Levo-bornyl acetate
• Bornyl acetate [USAN]
• Bornyl acetate, (-)-
• UNII-24QAP1VCUX
• 24QAP1VCUX
• Borneol, acetate, (1S,2R,4S)-(-)-
• (-)Bronyl acetate
• laevo-bornyl acetate
• (+/-)-Bornyl acetate
• EINECS 227-101-4
• BORNYL ACETATE, L-
• BORNYL ACETATE L-FORM
• BORNEOL, L-, ACETATE
• 1S-ENDO-BORNYL ACETATE
• Bornyl ethanoate
• DTXSID3052228
• FEMA NO. 4080
• BORNEOL ACETATE, (-)-
• (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate
• EC 227-101-4
• endo-bornyl acetate
• Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, acetate, (1S,2R,4S)-
• Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1S-endo)-
• Bornyl acetic ether
• 2-Camphanol acetate
• 2-Camphanyl acetate
• Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-, 2-acetate, (1R,2S,4R)-rel-
• 1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol acetate
• FEMA No. 2159
• UNII-213431586X
• L-Born-2-yl acetate
• [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
• (-)-Bornyl acetate, 95%
• 213431586X
• endo-1,7,7-Trimethylbicyclo(2.2.1)hept-2-yl acetate
• (1S)-1,7,7-TRIMETHYLBICYCLO(2.2.1)-2-HEPTANOL ACETATE
• EINECS 200-964-4
• Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, 2-acetate, (1R,2S,4R)-rel-
• Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, 2-acetate, (1S,2R,4S)-
• Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R,2S,4R)-rel-
• BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, ACETATE, (1S-ENDO)-
• Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1S,2R,4S)-
• NSC 407158
• AI3-00665
• Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, acetate, endo-
• DTXSID7041675
• Endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate
• L - born - 2 - yl acetate
• 1,7,7-Trimethylbicyclo(2.2.1)heptan-2-yl acetate, endo-
• Borneyl acetate
• (1R,2S,4R)-rel-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol 2-acetate
• Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R,2S,4R)-rel-
• NSC-407158
• (1R,2S,4R)-REL-1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPTAN-2-OL 2-ACETATE
• (-)-Bornylacetat
• (-)Bornyl acetate
• L-.alpha.-bornyl acetate
• 1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl acetate #
• BORNYL ACETATE [MI]
• BORNYL ACETATE [FCC]
• 1S-endo-Bornyl acetate; l-Bornyl acetate; levo-Bornyl acetate
• BORNYL ACETATE [FHFI]
• BORNYL ACETATE [INCI]
• SCHEMBL132358
• Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, endo-
• Biphenyl-4-carbothioicacidamide
• BORNYL ACETATE [MART.]
• Bornyl acetate, >=98%, FG
• (-)-[(1S)-bornyl]-acetate
• BORNYL ACETATE [WHO-DD]
• CHEMBL3186761
• DTXCID5030799
• L-BORNYL ACETATE [FHFI]
• HY-N0756A
• KGEKLUUHTZCSIP-HOSYDEDBSA-N
• BORNYL ACETATE L-FORM [MI]
• Tox21_303841
• [(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
• s3893
• AKOS017343145
• CCG-266560
• DB14665
• (-)-Bornyl acetate, analytical standard
• NCGC00357112-01
• AS-76314
• CAS-5655-61-8
• CS-0017052
• F16689
• (-)-BORNYL ACETATE (CONSTITUENT OF MYRRH)
• Q27105264
• (-)-BORNYL ACETATE (CONSTITUENT OF MYRRH) [DSC]
• [(1S,2R,4S)-1,7,7-Trimethylnorbornan-2-yl] acetate
• BORNYL ACETATE (CONSTITUENT OF CHAMOMILE) [DSC]
• F0001-1483
• (-)-Bornyl acetate, primary pharmaceutical reference standard
• [(1S,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.8764	87.64%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7367	73.67%
OATP2B1 inhibitior	-	0.8478	84.78%
OATP1B1 inhibitior	+	0.9080	90.80%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9204	92.04%
P-glycoprotein inhibitior	-	0.9504	95.04%
P-glycoprotein substrate	-	0.9580	95.80%
CYP3A4 substrate	+	0.6025	60.25%
CYP2C9 substrate	+	0.5963	59.63%
CYP2D6 substrate	-	0.8728	87.28%
CYP3A4 inhibition	-	0.9384	93.84%
CYP2C9 inhibition	-	0.9218	92.18%
CYP2C19 inhibition	-	0.7031	70.31%
CYP2D6 inhibition	-	0.9606	96.06%
CYP1A2 inhibition	-	0.9317	93.17%
CYP2C8 inhibition	-	0.8569	85.69%
CYP inhibitory promiscuity	-	0.9791	97.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5651	56.51%
Eye corrosion	-	0.8685	86.85%
Eye irritation	+	0.8582	85.82%
Skin irritation	+	0.7865	78.65%
Skin corrosion	-	0.9770	97.70%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7072	70.72%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.5533	55.33%
skin sensitisation	+	0.7661	76.61%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.6210	62.10%
Acute Oral Toxicity (c)	IV	0.4812	48.12%
Estrogen receptor binding	-	0.4915	49.15%
Androgen receptor binding	-	0.7982	79.82%
Thyroid receptor binding	-	0.7302	73.02%
Glucocorticoid receptor binding	-	0.8465	84.65%
Aromatase binding	-	0.8515	85.15%
PPAR gamma	-	0.7600	76.00%
Honey bee toxicity	-	0.7488	74.88%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9727	97.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.29%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.38%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.20%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	88.41%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.06%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.87%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.98%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.95%	89.05%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.36%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.44%	100.00%

Plants that contains it

• Abies alba
• Abies firma
• Abies grandis
• Abies sachalinensis var. mayriana
• Abies sibirica
• Achillea clypeolata
• Achillea millefolium
• Aconitum episcopale
• Acorus calamus
• Adina trichotoma
• Afraegle paniculata
• Agrimonia pilosa
• Alpinia flabellata
• Alpinia galanga
• Angelica acutiloba
• Angelica gigas
• Angelica japonica
• Angelica sinensis
• Ardisia humilis
• Artemisia annua
• Artemisia argyi
• Artemisia capillaris
• Artemisia montana
• Artemisia princeps
• Artemisia vulgaris
• Astragalus glycyphyllos
• Athanasia crithmifolia
• Athrixia elata
• Atractylodes lancea
• Baccharis truncata
• Benincasa hispida
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Calea sickii
• Cardamine heptaphylla
• Cassinia subtropica
• Centaurea benedicta
• Centaurea cheiranthifolia
• Centella asiatica
• Cerbera odollam
• Chamaecyparis obtusa
• Chloranthus fortunei
• Chrysanthemum indicum
• Chuquiraga erinacea
• Cistus clusii
• Cistus creticus
• Citrus × aurantium
• Citrus deliciosa
• Cladanthus arabicus
• Cneorum pulverulentum
• Cnidium monnieri
• Codonocarpus attenuatus
• Colchicum arenarium
• Crateva magna
• Cratoxylum formosum subsp. pruniflorum
• Cuphea hyssopifolia
• Cupressus nootkatensis
• Curcuma kwangsiensis
• Curcuma longa
• Curcuma phaeocaulis
• Curcuma wenyujin
• Cylindrolobus mucronatus
• Daphnandra johnsonii
• Dianella revoluta
• Diospyros verrucosa
• Elettaria cardamomum
• Elsholtzia ciliata
• Erythrina burttii
• Euonymus nanoides
• Euphorbia palustris
• Euphorbia pithyusa
• Farfugium japonicum
• Foeniculum vulgare
• Fouquieria diguetii
• Fritillaria monantha
• Garcinia oligantha
• Glehnia littoralis
• Grindelia hirsutula
• Gyrothyra underwoodiana
• Hippeastrum aulicum
• Holarrhena floribunda
• Houttuynia cordata
• Illicium difengpi
• Iris spuria
• Jacobaea erucifolia subsp. argunensis
• Jacobaea subalpina
• Juniperus communis
• Kokoona ochracea
• Lamprolobium fruticosum
• Lathyrus latifolius
• Leonurus japonicus
• Ligusticum striatum
• Lindera aggregata
• Litsea cubeba
• Lonicera japonica
• Machilus japonica
• Machilus obovatifolia
• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Magnolia obovata
• Magnolia officinalis
• Magnolia salicifolia
• Magnolia sprengeri
• Mentha pulegium
• Mentha suaveolens
• Mikania grazielae
• Monarda fistulosa
• Mosla chinensis
• Murraya exotica
• Murraya paniculata
• Myristica fragrans
• Nelumbo nucifera
• Nepeta multifida
• Ononis viscosa
• Paragynoxys meridana
• Pedicularis rex
• Perilla frutescens
• Periploca sepium
• Phyllolobium chinense
• Picea abies
• Picradeniopsis multiflora
• Pinus cembra
• Pinus edulis
• Pinus heldreichii
• Pinus koraiensis
• Pinus pumila
• Piper aduncum
• Piper callosum
• Piper cubeba
• Pittocaulon bombycophole
• Platycladus orientalis
• Pleogyne australis
• Polyachyrus sphaerocephalus
• Polygala amara
• Posidonia oceanica
• Prioria pinnata
• Pseudoconyza viscosa
• Psilostrophe villosa
• Pterocarpus erinaceus
• Pyrola decorata
• Pyrus bourgaeana
• Quercus serrata
• Rhodiola rosea
• Rubus allegheniensis
• Rubus pungens
• Rubus trifidus
• Salvia abrotanoides
• Salvia barrelieri
• Salvia broussonetii
• Salvia sclarea
• Sandoricum koetjape
• Sanguisorba minor
• Schisandra chinensis
• Schisandra sphenanthera
• Sedum sarmentosum
• Senna alexandrina
• Sideritis hirsuta
• Sideritis lanata
• Solidago canadensis
• Solidago gigantea
• Sorbus torminalis
• Stephania sutchuenensis
• Suaeda maritima
• Swertia japonica
• Syzygium cumini
• Tamarix gallica
• Tetraneuris acaulis
• Thujopsis dolabrata
• Thymus quinquecostatus
• Thymus vulgaris
• Torilis japonica
• Triunia erythrocarpa
• Unonopsis glaucopetala
• Valeriana hardwickii
• Valeriana jatamansi
• Valeriana officinalis
• Viola hondoensis
• Wurfbainia longiligularis
• Wurfbainia villosa
• Wurfbainia villosa var. xanthioides
• Zanthoxylum bungeanum
• Zanthoxylum schinifolium
• Zieria smithii
• Zingiber officinale

Cross-Links

• PubChem: 93009
• NPASS: NPC87828
• LOTUS: LTS0267397
• wikiData: Q104375352