Nootkatone

Details

• Internal ID: 1e906681-a20e-4870-9358-a5877d70c497
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• SMILES (Canonical): CC1CC(=O)C=C2C1(CC(CC2)C(=C)C)C
• SMILES (Isomeric): C[C@@H]1CC(=O)C=C2[C@]1(C[C@@H](CC2)C(=C)C)C
• InChI: InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
• InChI Key: WTOYNNBCKUYIKC-JMSVASOKSA-N
• Popularity: 268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33 g/mol
• Exact Mass: 218.167065321 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.90
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• (+)-Nootkatone
• 4674-50-4
• (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• IZ2Y119N4J
• DTXSID8047050
• CHEBI:81377
• 1(10),11-Eremophiladien-2-one
• 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
• DTXCID6027050
• FEMA NO. 4941
• 4Betah,5alpha-eremophila-1(10),11-dien-2-one
• 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one
• 4,4a,5,6,7,8-Hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone
• 4a,5-Dimethyl-1,2,3,4,4a,5,6,7-octahydro-7-keto-3-isopropenylnaphthalene
• 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, (4R-(4alpha,4aalpha,6beta))-
• 4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE
• RefChem:854683
• 225-124-4
• 942-649-0
• Nootkanone
• (+/-)-Nootkatone
• Nootkatone, (+/-)-
• (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• Nootkatone (+/-)-form [MI]
• UNII-3K3OKV2A5A
• 3K3OKV2A5A
• 4.beta.H,5.alpha.-Eremophila-1(10),11-dien-2-one
• 7betaH-Eremophila-1(10),11-dien-2-one -
• (4RS,4Asr,6RS)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone
• 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-rel
• MFCD04974578
• 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
• 28834-25-5
• Nootkatone (natural)
• Nootkatone, (+)-
• 5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one
• nootkaton
• UNII-IZ2Y119N4J
• FEMA No. 3166
• (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone; Nootkanone
• 2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R-(4.ALPHA.,4A.ALPHA.,6.BETA.))-
• EINECS 225-124-4
• NOOTKATONE [MI]
• NOOTKATONE [FHFI]
• (+)-Nootkatone, crystalline
• Nootkatone, >=98%, FG
• (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
• SCHEMBL110855
• CHEMBL446299
• orb1303434
• HSDB 8272
• HY-N2195
• Tox21_302385
• (+)-Nootkatone, analytical standard
• MSK014165
• s9071
• STL562310
• AKOS015955823
• CCG-266714
• (+)-Nootkatone, >=99.0% (GC)
• NCGC00256230-01
• 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R-(4alpha,4aalpha,6beta))-
• AC-34548
• AS-56160
• XN168139
• CAS-4674-50-4
• (+)-Nootkatone, technical, >=85% (GC)
• CS-0019503
• C17914
• F862860
• Q417896
• 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one
• 7.BETA.H-EREMOPHILA-1(10),11-DIEN-2-ONE -
• 5,6-DIMETHYL-8-ISOPROPENYL-BICYCLO(4,4,0)-DEC-1-EN-3-ONE
• (4R,4aS,6R)-6-isopropenyl-4,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLENE-ETHYL)-2(3H)-NAPHTHALENONE
• (4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one
• 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
• 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.9070	90.70%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4737	47.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9106	91.06%
OATP1B3 inhibitior	+	0.9115	91.15%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.8188	81.88%
P-glycoprotein inhibitior	-	0.9187	91.87%
P-glycoprotein substrate	-	0.8212	82.12%
CYP3A4 substrate	+	0.5593	55.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.7789	77.89%
CYP2C9 inhibition	-	0.8379	83.79%
CYP2C19 inhibition	-	0.6023	60.23%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.7782	77.82%
CYP2C8 inhibition	-	0.9009	90.09%
CYP inhibitory promiscuity	-	0.8417	84.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4722	47.22%
Eye corrosion	-	0.9797	97.97%
Eye irritation	-	0.6129	61.29%
Skin irritation	+	0.5880	58.80%
Skin corrosion	-	0.9714	97.14%
Ames mutagenesis	-	0.8783	87.83%
Human Ether-a-go-go-Related Gene inhibition	-	0.4222	42.22%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.7617	76.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5637	56.37%
Acute Oral Toxicity (c)	III	0.8367	83.67%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.5912	59.12%
Thyroid receptor binding	-	0.7336	73.36%
Glucocorticoid receptor binding	-	0.6114	61.14%
Aromatase binding	+	0.7839	78.39%
PPAR gamma	-	0.6966	69.66%
Honey bee toxicity	-	0.8720	87.20%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.99%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.88%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.78%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.60%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.02%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	89.40%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.11%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.28%	96.43%
CHEMBL1902	P62942	FK506-binding protein 1A	84.04%	97.05%
CHEMBL340	P08684	Cytochrome P450 3A4	83.20%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.21%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.06%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.80%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.57%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	81.35%	95.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.58%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.45%	93.04%

Plants that contains it

• Aconitum contortum
• Ageratum houstonianum
• Alpinia oxyphylla
• Alpinia zerumbet
• Alstonia spectabilis
• Arnica parryi
• Buxus hildebrandtii
• Callicarpa acuminata
• Ceriops tagal
• Citrus × aurantium
• Citrus maxima
• Citrus medica
• Corydalis conspersa
• Cotinus coggygria
• Crataegus germanica
• Croton geayi
• Cussonia bancoensis
• Cymopterus terebinthinus
• Cyperus rotundus
• Dalbergia nitidula
• Dendrobium nobile
• Drypetes tessmanniana
• Echinacea simulata
• Eremurus chinensis
• Escontria chiotilla
• Eucryphia cordifolia
• Gratiola officinalis
• Gynochthodes parvifolia
• Hypericum reptans
• Inula helenium
• Juniperus brevifolia
• Juniperus communis
• Kalanchoe integra
• Kniphofia foliosa
• Ligustrum ovalifolium
• Mandragora officinarum
• Melaleuca rugulosa
• Mikania luetzelburgii
• Neolitsea villosa
• Nicoteba betonica
• Pachygone dasycarpa
• Petunia axillaris
• Pittosporum brevicalyx
• Rubus nemoralis
• Salvia officinalis subsp. lavandulifolia
• Saussurea salicifolia
• Sideritis grandiflora
• Solanum euacanthum
• Strychnos amazonica
• Tamarix senegalensis
• Uncaria africana
• Ungernia victoris
• Uvaria lucida
• Verbena officinalis
• Viguiera pinnatilobata

Cross-Links

• PubChem: 1268142
• NPASS: NPC127582
• ChEMBL: CHEMBL446299
• LOTUS: LTS0183338
• wikiData: Q417896