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(+)-medioresinol

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c(c(c1)OC)O
InChI	InChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21+/m0/s1
InChIKey	VJOBNGRIBLNUKN-BMHXQBNDSA-N
Formula	C₂₁H₂₄O₇
HBA	7
HBD	2
MW	388.42
Rotatable Bonds	5
TPSA	86.61
LogP	3.2
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	388.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eryngium triquetrum	Umbelliferae	Plantae	1094608

Showing of synonyms

Bouzergoune F, Ciavatta M.L, et al. (2016). Phytochemical Study of Eryngium triquetrum: Isolation of Polyacetylenes and Lignans. Planta Med,2016,82(16),1438-1445. [View] [PubMed]

Pubchem: 181681

Cas: 40957-99-1

Gnps: CCMSLIB00006716241

Zinc: ZINC000005665084

Chebi: 67644

Nmrshiftdb2: 60030699

Metabolights: MTBLC67644

Chembl: CHEMBL376507

CPRiL: 61312

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 388.42 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 388.42 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 388.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 388.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.7
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.910
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.020
Plasma Protein Binding: 75.73
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-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: 11.520
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.520
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.740
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.930
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -17.760
Rat (Acute): 2.120
Rat (Chronic Oral): 2.330
Fathead Minnow: 4.080
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 442.810
Hydration Free Energy: -5.640
Log(D) at pH=7.4: 2.930
Log(P): 1.62
Log S: -4.56
Log(Vapor Pressure): -8.49
Melting Point: 167.91
pKa Acid: 8.43
pKa Basic: 3.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9591
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9450
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9441
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9279
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9276
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9254
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.9238
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.9228
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9191
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9175
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9072
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9064
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8990
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8956
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8834
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8792
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8711
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8628
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8621
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.8613
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8409
cAMP-dependent protein kinase catalytic subunit alpha	P05132	KAPCA_MOUSE	Mus musculus	5	0.8397
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8359
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8350
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8312
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8265
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8262
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8209
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	4	0.8206
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8197
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8166
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8128
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8096
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8048
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8032
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7997
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7939
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7929
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7924
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.7875
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7862
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	4	0.7837
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	4	0.7820
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	4	0.7810
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7808
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7791
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7723
Uridine phosphorylase 2	O95045	UPP2_HUMAN	Homo sapiens	4	0.7719
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7716
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7672
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7648
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7646
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7617
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7601
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7584
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.7555
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7540
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7536
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	4	0.7526
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	4	0.7526
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7521
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7519
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7482
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7464
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7460
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7451
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7414
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7409
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7397
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7396
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7383
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7362
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7362
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7355
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7350
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7350
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7322
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7307
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7306
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7306
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7303
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.7290
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7279
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7268
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7263
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7259
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7259
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7239
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7238
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7237
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7227
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7227
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7225
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7212
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7210
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7208
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7206
ATP-dependent protease subunit HslV	P0A7B8	HSLV_ECOLI	Escherichia coli	3	0.7202
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7195
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7195
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7193
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7179
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7169
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7168
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7165
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7162
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7162
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7158
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7157
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7157
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7156
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7155
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7149
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7149
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7147
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7144
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7141
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7123
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7122
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7118
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7105
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7100
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7096
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7090
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7081
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7080
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7065
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7064
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7063
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7062
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7060
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7056
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7051
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7034
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7034
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7032
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7031
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7030
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7029
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7014
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7014
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7009

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