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10-isobutyryloxy-8,9-dihydro-8,9-epoxythymol-isobutyrate

Family: Asteraceae-Compositae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene

Canonical Smiles	Cc1ccc(c(c1)OC(=O)C(C)C)C1(COC(=O)C(C)C)OC1
InChI	InChI=1S/C18H24O5/c1-11(2)16(19)21-9-18(10-22-18)14-7-6-13(5)8-15(14)23-17(20)12(3)4/h6-8,11-12H,9-10H2,1-5H3
InChIKey	OLARKEMZPWGFJU-UHFFFAOYSA-N
Formula	C₁₈H₂₄O₅
HBA	5
HBD	0
MW	320.39
Rotatable Bonds	6
TPSA	65.13
LogP	2.98
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	320.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Asteriscus pygmaeus	Asteraceae-Compositae	Plantae	56520
2	Pulicaria arabica	Asteraceae-Compositae	Plantae	119185

Showing of synonyms

Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
Ahmed AA (1992). Farnesol and thymol derivatives from Asteriscus pygmaeus.. Journal of Natural Products,1992,55(6),824-827. [View]

Pubchem: 11472669

Cas: 22518-06-5

Gnps: CCMSLIB00006442629

Chebi: 168879

Nmrshiftdb2: 60078924

Chembl: CHEMBL1417148

No compound-protein relationship available.

SMILES: O1CC1c2ccccc2

Level: 1

Mol. Weight: 120.15 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 44.05 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.84
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.47
Plasma Protein Binding: 28.13
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 15.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.69
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.08
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.76
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 2.5
Rat (Acute): 2.55
Rat (Chronic Oral): 2.03
Fathead Minnow: 4.59
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 339.48
Hydration Free Energy: -6.08
Log(D) at pH=7.4: 3.05
Log(P): 3.58
Log S: -4.68
Log(Vapor Pressure): -4.76
Melting Point: 18.22
pKa Acid: 8.75
pKa Basic: 2.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9234
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9234
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9019
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9019
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8699
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8699
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8566
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8566
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8529
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8529
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8186
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8186
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8152
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8152
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8136
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8136
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8115
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8115
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8099
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8099
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8075
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8075
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8062
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8062
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8049
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8049
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8007
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8007
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7892
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7892
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7784
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7784
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7661
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7661
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7621
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7621
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7604
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7604
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7457
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7457
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7438
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7438
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7435
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7435
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7397
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7397
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7362
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7362
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7348
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7348
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7344
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7344
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7339
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7339
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7338
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7338
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7338
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7338
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7329
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7329
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7315
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7315
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7279
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7279
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7276
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7276
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7265
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7265
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7242
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7242
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7221
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7221
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7209
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7209
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7207
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7207
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7200
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7200
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7190
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7190
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7188
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7188
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7187
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7187
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7180
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7180
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7176
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7176
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7165
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7165
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7146
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7146
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7138
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7138
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7097
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7097
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7095
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7095
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7091
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7091
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7083
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7083
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7068
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7068
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7063
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7063
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7061
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7061
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7060
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7060
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7038
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7038
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7011
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7011
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.7010
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.7010

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