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Epieudesmin

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)OC)OC
InChI	InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21-,22+/m0/s1
InChIKey	PEUUVVGQIVMSAW-WWLNLUSPSA-N
Formula	C₂₂H₂₆O₆
HBA	6
HBD	0
MW	386.44
Rotatable Bonds	6
TPSA	55.38
LogP	3.8
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	386.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eremophila maculata	Scrophulariaceae	Plantae	1214565

Showing of synonyms

Youssef F.S, Ashour M.L, et al. (2016). Eremophila maculata —Isolation of a rare naturally-occurring lignan glycoside and the hepatoprotective activity of the leaf extract. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2016, 23(12), 1484-1493. [View] [PubMed]

Pubchem: 7000209

Cas: 60102-89-8

Zinc: ZINC000012371281

Nmrshiftdb2: 60075563

Chembl: CHEMBL512865

No compound-protein relationship available.

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 386.44 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 386.44 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 386.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.580
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.130
Plasma Protein Binding: 77.7
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.730
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.340
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.390
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.560
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: Toxic
T. Pyriformis: -22.120
Rat (Acute): 2.620
Rat (Chronic Oral): 1.810
Fathead Minnow: 4.510
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: 445.570
Hydration Free Energy: -5.080
Log(D) at pH=7.4: 2.640
Log(P): 2.99
Log S: -3.97
Log(Vapor Pressure): -7.13
Melting Point: 135.14
pKa Acid: 10.29
pKa Basic: 3.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9767
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9694
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9479
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9462
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9378
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9154
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9137
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8995
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8986
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8941
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	4	0.8940
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8938
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8857
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8782
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8611
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8591
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8574
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8570
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8554
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.8500
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8417
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8404
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8224
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8219
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8144
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8120
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8101
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.8056
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7990
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7988
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	4	0.7980
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7974
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7955
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7928
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7910
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7868
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7848
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7835
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7816
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7798
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7771
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7770
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7758
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7712
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7707
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7682
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7654
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7653
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7625
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7586
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7548
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7523
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7510
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7506
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7484
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7483
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7469
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7463
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7463
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7446
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7445
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	2	0.7435
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7435
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7429
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7428
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7419
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7410
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7399
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7395
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7395
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7393
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7382
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7380
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7378
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7373
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7370
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7370
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7367
Cartilage oligomeric matrix protein	P35444	COMP_RAT	Rattus norvegicus	3	0.7363
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7363
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7361
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7352
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7350
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7345
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7326
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7325
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7317
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7311
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7310
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7309
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7304
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7299
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7299
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7295
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7288
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7287
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7278
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7274
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7271
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7264
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7262
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7258
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7256
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7254
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7249
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	4	0.7242
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7233
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7225
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7224
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7223
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7223
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7218
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7217
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7207
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7202
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7193
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7180
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7177
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7176
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7171
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7158
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7154
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7145
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7139
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7138
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7127
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7126
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7114
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7111
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7109
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7108
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7100
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7097
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7093
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7091
Retinol-binding protein 4	P02753	RET4_HUMAN	Homo sapiens	3	0.7078
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7078
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	4	0.7074
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7073
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7070
DNA double-strand break repair protein Mre11	Q9X1X0	Q9X1X0_THEMA	Thermotoga maritima MSB8	3	0.7065
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7063
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7058
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7054
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7035
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7033
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7024
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7023
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7019
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7019
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7013
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7013
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7011
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7011
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7008
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7002

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