Hinokitiol

Details

• Internal ID: 71a6a800-f607-4bcd-a575-9f4c5d7ff181
• Taxonomy: Hydrocarbon derivatives > Tropones > Tropolones
• IUPAC Name: 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
• SMILES (Canonical): CC(C)C1=CC(=O)C(=CC=C1)O
• SMILES (Isomeric): CC(C)C1=CC(=O)C(=CC=C1)O
• InChI: InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
• InChI Key: FUWUEFKEXZQKKA-UHFFFAOYSA-N
• Popularity: 478 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: 2.10
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• beta-Thujaplicin
• 499-44-5
• 4-Isopropyltropolone
• Hinokitol
• beta-Thujaplicine
• Isopropyltropolone
• THUJAPLICIN, BETA
• Tropolone, 4-isopropyl-
• .beta.-Thujaplicin
• beta-Isopropyltropolon
• 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one
• 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
• .beta.-Isopropyltropolon
• b-Thujaplicin
• 2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one
• NSC 18804
• .beta.-Thujaplicine
• 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
• NSC18804
• 2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one
• EINECS 207-880-7
• BRN 2045206
• UNII-U5335D6EBI
• CHEMBL48310
• AI3-28398
• MLS001048906
• 2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
• Hinokitiol 4-Isopropyltropolone
• U5335D6EBI
• 2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-one
• CHEBI:10447
• NSC-18804
• 2-hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-one
• SMR000387099
• 2,4,6-CYCLOHEPTATRIEN-1-ONE, 2-HYDROXY-4-ISOPROPYL-
• |A-Thujaplicin
• 4-08-00-00488 (Beilstein Handbook Reference)
• -thujaplicin
• ss-Thujaplicine
• |A-thujaplici
• beta -thujaplicin
• beta -thujaplicine
• 6-Isopropyl-tropolon
• Thujaplicin, .beta.
• 4-isopropyl-tropolone
• beta -isopropyltropolon
• beta-Thujaplicin, 99%
• 4(6)-Isopropyltropolone
• HINOKITIOL [INCI]
• D0H4YW
• NCIMech_000141
• cid_3611
• HINOKITIOL [WHO-DD]
• BSPBio_001025
• KBioGR_000365
• KBioSS_000365
• BIDD:ER0491
• SCHEMBL158795
• SPECTRUM1505160
• 2-hydroxy-6-isopropyl-cyclohepta-2,4,6-trien-1-one
• DTXSID6043911
• BDBM79632
• FUWUEFKEXZQKKA-UHFFFAOYSA-
• KBio2_000365
• KBio2_002933
• KBio2_005501
• KBio3_000709
• KBio3_000710
• WLN: L7VJ BQ DY1&1
• .BETA.-THUJAPLICIN [MI]
• AMY3994
• Bio2_000343
• Bio2_000823
• HMS1362C07
• HMS1792C07
• HMS1990C07
• HMS2269D23
• HMS3403C07
• HY-B2230
• BBL036671
• BDBM50330794
• CCG-35378
• MFCD00040180
• s4771
• STL559050
• AKOS015895184
• AKOS037515521
• CS-7724
• KS-5297
• IDI1_002098
• QTL1_000044
• NCGC00094565-01
• NCGC00094565-02
• NCGC00094565-03
• NCGC00094565-04
• NCGC00094565-05
• NCGC00179338-01
• LS-56183
• NCI60_001565
• FT-0603426
• H0142
• C09904
• C75327
• D04876
• EN300-222362
• beta-Thujaplicin, SAJ special grade, >=99.0%
• 2-Hydroxy-4-isopropyl-2,6-cycloheptatrien-1-one
• 2-Hydroxy-4-isopropyl-cyclohepta-2,4,6-trienone
• 2-Hydroxy-6-isopropyl-2,4,6-cycloheptene-1-one
• A923788
• SR-01000737397
• 2,6-Cycloheptatrien-1-one, 2-hydroxy-4-isopropyl-
• 2-hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-one
• J-521461
• Q2705171
• SR-01000737397-2
• 2-Hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-one
• 2-Hydroxy-4-isopropyl-cyclohepta-2,4,6-trien-1-one
• BRD-K37691127-001-02-2
• 2-hydroxy-6-propan-2-yl-1-cyclohepta-2,4,6-trienone
• 2-oxidanyl-6-propan-2-yl-cyclohepta-2,4,6-trien-1-one
• Z1255485978
• 2,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
• (2E,4Z,6Z)-2-hydroxy-4-isopropylcyclohepta-2,4,6-trienone
• 2-Hydroxy-4(6)-(1-methylethyl)-2,4,6-cycloheptatrien-1-one, 9CI
• 2- hydroxy- 4- isopropyl- 2, 4, 6- cyclohepta- 2, 4, 6- trien- 1- one
• InChI=1/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8476	84.76%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8908	89.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9625	96.25%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9412	94.12%
P-glycoprotein inhibitior	-	0.9689	96.89%
P-glycoprotein substrate	-	0.9561	95.61%
CYP3A4 substrate	-	0.6998	69.98%
CYP2C9 substrate	-	0.5701	57.01%
CYP2D6 substrate	-	0.8073	80.73%
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	-	0.9931	99.31%
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	+	0.9884	98.84%
Skin irritation	+	0.7996	79.96%
Skin corrosion	+	0.9536	95.36%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8560	85.60%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	+	0.6533	65.33%
skin sensitisation	+	0.8506	85.06%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.6470	64.70%
Acute Oral Toxicity (c)	III	0.8533	85.33%
Estrogen receptor binding	-	0.8188	81.88%
Androgen receptor binding	-	0.6054	60.54%
Thyroid receptor binding	-	0.6552	65.52%
Glucocorticoid receptor binding	-	0.8787	87.87%
Aromatase binding	-	0.7847	78.47%
PPAR gamma	-	0.8322	83.22%
Honey bee toxicity	-	0.9490	94.90%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8145	81.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	39810.7 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	2511.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	631 nM; 631 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1937	Q92769	Histone deacetylase 2	15.44 nM	Ki	PMID: 24900743
CHEMBL3192	Q9BY41	Histone deacetylase 8	177.95 nM	Ki	PMID: 24900743
CHEMBL5514	P42858	Huntingtin	8912.5 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	7943.3 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	8912.5 nM	Potency	via CMAUP
CHEMBL1973	P14679	Tyrosinase	8980 nM	IC50	PMID: 25288494
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.50%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	96.93%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.36%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.78%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.54%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.78%	99.15%
CHEMBL2535	P11166	Glucose transporter	90.49%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	86.41%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.84%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.81%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.31%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.62%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.07%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.72%	89.00%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	80.23%	98.33%

Plants that contains it

• Calocedrus formosana
• Chamaecyparis obtusa
• Hesperocyparis abramsiana
• Hesperocyparis macrocarpa
• Juniperus communis
• Rheum rhabarbarum
• Thuja occidentalis
• Thuja plicata
• Thujopsis dolabrata
• Thujopsis dolabrata var. dolabrata

Cross-Links

• PubChem: 3611
• NPASS: NPC46565
• ChEMBL: CHEMBL48310
• LOTUS: LTS0053731
• wikiData: Q2705171