Nootkatin

Details

• Internal ID: 84ad5cfb-2e7f-4606-badc-7542a5f6632c
• Taxonomy: Hydrocarbon derivatives > Tropones > Tropolones
• IUPAC Name: 2-hydroxy-5-(3-methylbut-2-enyl)-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
• SMILES (Canonical): CC(C)C1=CC(=O)C(=CC=C1CC=C(C)C)O
• SMILES (Isomeric): CC(C)C1=CC(=O)C(=CC=C1CC=C(C)C)O
• InChI: InChI=1S/C15H20O2/c1-10(2)5-6-12-7-8-14(16)15(17)9-13(12)11(3)4/h5,7-9,11H,6H2,1-4H3,(H,16,17)
• InChI Key: MNMNTZYOZZLKSV-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• NSC43339
• 4431-03-2
• MLS002608535
• NSC 43339
• 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-5-(3-methyl-2-butenyl)-4-(1-methylethyl)-
• NSC 403527
• CHEMBL1700891
• SCHEMBL13311346
• DTXSID10196125
• MNMNTZYOZZLKSV-UHFFFAOYSA-N
• HMS3091E24
• NSC-43339
• NSC403527
• NSC-403527
• SMR001527282
• Q67880029
• 2-hydroxy-4-isopropyl-5-(3-methylbut-2-enyl)cyclohepta-2,4,6-trien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9171	91.71%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6656	66.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9579	95.79%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8452	84.52%
P-glycoprotein inhibitior	-	0.9468	94.68%
P-glycoprotein substrate	-	0.9171	91.71%
CYP3A4 substrate	-	0.6252	62.52%
CYP2C9 substrate	+	0.6045	60.45%
CYP2D6 substrate	-	0.7840	78.40%
CYP3A4 inhibition	-	0.8198	81.98%
CYP2C9 inhibition	-	0.6878	68.78%
CYP2C19 inhibition	+	0.5088	50.88%
CYP2D6 inhibition	-	0.7964	79.64%
CYP1A2 inhibition	+	0.6691	66.91%
CYP2C8 inhibition	-	0.9699	96.99%
CYP inhibitory promiscuity	-	0.5066	50.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7139	71.39%
Carcinogenicity (trinary)	Non-required	0.6550	65.50%
Eye corrosion	-	0.8487	84.87%
Eye irritation	+	0.8043	80.43%
Skin irritation	+	0.5840	58.40%
Skin corrosion	+	0.5190	51.90%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6342	63.42%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	+	0.8263	82.63%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.5542	55.42%
Acute Oral Toxicity (c)	III	0.8167	81.67%
Estrogen receptor binding	-	0.8374	83.74%
Androgen receptor binding	-	0.7544	75.44%
Thyroid receptor binding	-	0.5120	51.20%
Glucocorticoid receptor binding	-	0.5113	51.13%
Aromatase binding	-	0.5869	58.69%
PPAR gamma	+	0.5633	56.33%
Honey bee toxicity	-	0.8723	87.23%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9751	97.51%

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	98.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.07%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.33%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.75%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.15%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	91.23%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.38%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.96%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.34%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.36%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.63%	96.12%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.22%	93.99%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.40%	85.30%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Cupressus torulosa
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus communis
• Juniperus osteosperma
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rheum rhabarbarum
• Rhodanthe stricta
• Schisandra chinensis
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 238797
• NPASS: NPC297280
• LOTUS: LTS0127144
• wikiData: Q67880029