gamma-Thujaplicin

Details

• Internal ID: a51929a6-0a01-40f8-b9f6-29c7f383acbd
• Taxonomy: Hydrocarbon derivatives > Tropones > Tropolones
• IUPAC Name: 2-hydroxy-5-propan-2-ylcyclohepta-2,4,6-trien-1-one
• SMILES (Canonical): CC(C)C1=CC=C(C(=O)C=C1)O
• SMILES (Isomeric): CC(C)C1=CC=C(C(=O)C=C1)O
• InChI: InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)
• InChI Key: WKEWHSLZDDZONF-UHFFFAOYSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20 g/mol
• Exact Mass: 164.083729621 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 5-Isopropyltropolone
• 672-76-4
• gamma-Thujaplicine
• THUJAPLICIN, ALPHA
• .gamma.-Thujaplicin
• 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-5-(1-methylethyl)-
• NSC43338
• .gamma.-Thujaplicine
• 2-Hydroxy-5-isopropyl-2,4,6-cycloheptatrien-1-one
• NSC 18805
• NSC 43338
• NSC402794
• CA2K6LJ2BV
• NSC 402794
• BRN 2044323
• 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-5-isopropyl-
• 2-hydroxy-5-propan-2-ylcyclohepta-2,4,6-trien-1-one
• AI3-28399
• MLS002608534
• MLS002702822
• CHEMBL1275999
• CHEBI:10578
• NSC18805
• NSC-18805
• NSC-43338
• NSC-402794
• 2-Hydroxy-5-isopropyl- 2,4,6-cycloheptatrienone
• 4-08-00-00495 (Beilstein Handbook Reference)
• 2-hydroxy-5-isopropyl-cyclohepta-2,4,6-trien-1-one
• WLN: L7VJ BQ EY1&1
• SMR001527281
• 2,6-Cycloheptatrien-1-one, 2-hydroxy-5-isopropyl-
• 2,6-Cycloheptatrien-1-one, 2-hydroxy-5-(1-methylethyl)-
• | pound-Thujaplicin
• Thujaplicin, .alpha.
• THUJAPLICIN, A-
• UNII-CA2K6LJ2BV
• D0Z1XR
• NCIMech_000101
• DTXSID2060969
• SCHEMBL10668692
• WKEWHSLZDDZONF-UHFFFAOYSA-N
• BDBM50330795
• CCG-35377
• AKOS006276241
• LS-56189
• NCI60_001566
• FT-0657915
• C09905
• A835689
• 2-Hydroxy-5-isopropylcyclohepta-2,4,6-trien-1-one
• 2-hydroxy-5-isopropyl-2,4,6-cycloheptatriene-1-one
• Q27108661
• 2-Hydroxy-5-isopropyl-2,4,6-cycloheptatrien-1-one #
• 2-hydroxy-5-propan-2-yl-1-cyclohepta-2,4,6-trienone
• 2-oxidanyl-5-propan-2-yl-cyclohepta-2,4,6-trien-1-one
• 2-Hydroxy-5-(1-methylethyl)-2,4,6-cycloheptatrien-1-one
• 2-hydroxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8465	84.65%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8908	89.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9602	96.02%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9597	95.97%
P-glycoprotein inhibitior	-	0.9794	97.94%
P-glycoprotein substrate	-	0.9783	97.83%
CYP3A4 substrate	-	0.7548	75.48%
CYP2C9 substrate	-	0.5618	56.18%
CYP2D6 substrate	-	0.7601	76.01%
CYP3A4 inhibition	-	0.9274	92.74%
CYP2C9 inhibition	-	0.9145	91.45%
CYP2C19 inhibition	-	0.8522	85.22%
CYP2D6 inhibition	-	0.9010	90.10%
CYP1A2 inhibition	+	0.5091	50.91%
CYP2C8 inhibition	-	0.9957	99.57%
CYP inhibitory promiscuity	-	0.9090	90.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7111	71.11%
Carcinogenicity (trinary)	Non-required	0.7025	70.25%
Eye corrosion	+	0.9292	92.92%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7996	79.96%
Skin corrosion	+	0.9536	95.36%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8077	80.77%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	+	0.8506	85.06%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	+	0.5444	54.44%
Acute Oral Toxicity (c)	III	0.8533	85.33%
Estrogen receptor binding	-	0.6685	66.85%
Androgen receptor binding	-	0.5981	59.81%
Thyroid receptor binding	-	0.7630	76.30%
Glucocorticoid receptor binding	-	0.8346	83.46%
Aromatase binding	-	0.8112	81.12%
PPAR gamma	-	0.9161	91.61%
Honey bee toxicity	-	0.9464	94.64%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6127	61.27%
Fish aquatic toxicity	+	0.8145	81.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	1150 nM	IC50	PMID: 25288494

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.80%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.18%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	91.60%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.14%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.39%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.92%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.64%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.31%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.23%	100.00%

Plants that contains it

• Calocedrus decurrens
• Hesperocyparis abramsiana
• Hesperocyparis macrocarpa
• Tetraclinis articulata
• Thuja occidentalis
• Thuja plicata
• Thujopsis dolabrata

Cross-Links

• PubChem: 12649
• NPASS: NPC229046
• ChEMBL: CHEMBL1275999
• LOTUS: LTS0023908
• wikiData: Q27108661