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Catalponol

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Quinone
- Subclass: Naphthoquinone

Canonical Smiles	CC(=CC[C@@H]1C[C@H](O)c2c(C1=O)cccc2)C
InChI	InChI=1S/C15H18O2/c1-10(2)7-8-11-9-14(16)12-5-3-4-6-13(12)15(11)17/h3-7,11,14,16H,8-9H2,1-2H3/t11-,14+/m1/s1
InChIKey	BTQXIESSQVRLCV-RISCZKNCSA-N
Formula	C₁₅H₁₈O₂
HBA	2
HBD	1
MW	230.31
Rotatable Bonds	2
TPSA	37.3
LogP	3.28
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	17
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	230.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Artemisia arborescens	Asteraceae	Plantae	72386

Showing of synonyms

Abderrahim A, Belhamel K, et al. (2010). Chemical composition of the essential oil from Artemisia arborescens L. growing wild in Algeria.. Records of Natural Products,2010,4(1),87-90. [View]

Pubchem: 169570

Cas: 34168-56-4

Zinc: ZINC000005158854

Nmrshiftdb2: 60075753

Chembl: CHEMBL496250

Comptox: DTXSID70187771

CPRiL: 267113

SMILES: c1cccc(c12)CCCC2=O

Level: 0

Mol. Weight: 230.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.58
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.18
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 74.58
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 7.36
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.47
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.41
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: 0.47
Rat (Acute): 2.48
Rat (Chronic Oral): 2.11
Fathead Minnow: 4.11
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: 325.8
Hydration Free Energy: -8.57
Log(D) at pH=7.4: 2.2
Log(P): 3.0
Log S: -3.13
Log(Vapor Pressure): -5.27
Melting Point: 74.36
pKa Acid: 10.09
pKa Basic: 4.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8837
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8837
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8752
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8752
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8591
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8591
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8536
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8536
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8505
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8505
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.8410
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.8410
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8306
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8306
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8281
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8281
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8087
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8087
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8082
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8082
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8067
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8067
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7947
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7947
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7938
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7938
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7926
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7926
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7856
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7856
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7815
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7815
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7812
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7812
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7809
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7809
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7733
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7733
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7730
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7730
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7715
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7715
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7629
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7629
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7602
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7602
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7555
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7555
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7546
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7546
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7538
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7538
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7528
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7528
Fumarate reductase subunit D	P0A8Q3	FRDD_ECOLI	Escherichia coli	3	0.7507
Fumarate reductase subunit D	P0A8Q3	FRDD_ECOLI	Escherichia coli	3	0.7507
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7499
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7499
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7487
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7487
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7464
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7464
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7402
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7402
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7399
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7399
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7392
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7392
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7382
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7382
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7377
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7377
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7376
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7376
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7371
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7371
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7369
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7369
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7357
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7357
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7342
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7342
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7327
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7327
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7327
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7327
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7325
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7325
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7271
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7271
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7193
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7193
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7189
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7189
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7180
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7180
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7179
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7179
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7174
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7174
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7170
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7170
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7162
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7162
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7159
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7159
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7154
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7154
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7147
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7147
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7117
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7117
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7101
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7101
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7071
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7071
Protease	O38708	O38708_9HIV1	Human immunodeficiency virus 1	3	0.7067
Protease	O38708	O38708_9HIV1	Human immunodeficiency virus 1	3	0.7067
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7062
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7062
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7060
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7060
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7053
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7053
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7048
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7048
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7047
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7047
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7038
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7038
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7031
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7031
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7018
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7018

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