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Ephedralone

Family: Plantae - Ephedraceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Quinolone Alkaloid

Canonical Smiles	COc1ccc2c(c1)[nH]c(cc2=O)C(=O)O
InChI	InChI=1S/C11H9NO4/c1-16-6-2-3-7-8(4-6)12-9(11(14)15)5-10(7)13/h2-5H,1H3,(H,12,13)(H,14,15)
InChIKey	JUQPPCMGDXBUFQ-UHFFFAOYSA-N
Formula	C₁₁H₉NO₄
HBA	3
HBD	2
MW	219.2
Rotatable Bonds	2
TPSA	79.39
LogP	1.23
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	16
Formal Charge	0
Fraction CSP3	0.09
Exact Mass	219.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ephedra alata	Ephedraceae	Plantae	302006
2	Ephedra aphylla	Ephedraceae	Plantae	191304

Showing of synonyms

Nawwar MAM, Barakat HH, et al. (1985). Alkaloidal, lignan and phenolic constituents of Ephedra alata. Phytochemistry,1985,24(4),878-879. [View]
Hussein SAM, Barakat HH, et al. (1997). Flavonoids from Ephedra aphylla. Phytochemistry,1997,45(7),1529-1532. [View]

Pubchem: 13223157

Cas: 77474-33-0

Zinc: ZINC000013821195

Nmrshiftdb2: 60024710

Chembl: CHEMBL22527

Comptox: DTXSID40529644

No compound-protein relationship available.

SMILES: c1cccc(c12)[nH]ccc2=O

Level: 0

Mol. Weight: 219.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.870
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 48.98
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: Non-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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.780
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.480
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.680
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.090
Micronucleos: Toxic
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: 3.820
Rat (Acute): 1.810
Rat (Chronic Oral): 2.970
Fathead Minnow: 3.860
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 369.280
Hydration Free Energy: -12.130
Log(D) at pH=7.4: -1.230
Log(P): 1.52
Log S: -3.9
Log(Vapor Pressure): -7.47
Melting Point: 259.76
pKa Acid: 5.72
pKa Basic: 6.44

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9680
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9680
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9525
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9525
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.9524
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.9524
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9333
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9333
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8999
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8999
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8998
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8998
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.8807
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.8807
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8797
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8797
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	3	0.8792
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	3	0.8792
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.8757
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	4	0.8757
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.8757
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	4	0.8757
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8744
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8744
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8724
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8724
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8614
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8614
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8593
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8593
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	3	0.8564
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	3	0.8564
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.8489
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.8489
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8411
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8411
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.8291
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.8291
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.8210
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.8210
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8190
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8190
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7987
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7987
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7882
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7882
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7878
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7878
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7844
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7844
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7843
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7843
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.7825
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.7825
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7822
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7822
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7791
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7791
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7696
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7696
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7679
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7679
Deoxycytidylate deaminase	H6WFU3	H6WFU3_9CAUD	Cyanophage S-TIM5	4	0.7649
Deoxycytidylate deaminase	H6WFU3	H6WFU3_9CAUD	Cyanophage S-TIM5	4	0.7649
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7643
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7643
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7638
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7638
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7555
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7555
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7508
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7508
Malate synthase G	P9WK17	MASZ_MYCTU	Mycobacterium tuberculosis	3	0.7466
Malate synthase G	P9WK17	MASZ_MYCTU	Mycobacterium tuberculosis	3	0.7466
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7465
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7465
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7462
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7462
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7429
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7429
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7364
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7364
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7360
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7360
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7322
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7322
Aminotransferase class I/classII domain-containing protein	O57946	O57946_PYRHO	Pyrococcus horikoshii	3	0.7283
Aminotransferase class I/classII domain-containing protein	O57946	O57946_PYRHO	Pyrococcus horikoshii	3	0.7283
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7268
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7268
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	4	0.7257
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	4	0.7257
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7253
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7253
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7249
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7249
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7216
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7216
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7213
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7213
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7196
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7196
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7186
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7186
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7160
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7160
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7144
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7144
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7124
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7124
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7116
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7116
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	2	0.7104
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	2	0.7104
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7094
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7094
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7086
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7086
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7080
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7080
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7075
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7075
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7045
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7045
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7036
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7036
Egl nine homolog 1	Q9GZT9	EGLN1_HUMAN	Homo sapiens	2	0.7034
Egl nine homolog 1	Q9GZT9	EGLN1_HUMAN	Homo sapiens	2	0.7034
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7013
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7013
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7008
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7008

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