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Ficusal

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	O=Cc1cc(OC)c2c(c1)[C@@H](CO)[C@@H](O2)c1ccc(c(c1)OC)O
InChI	InChI=1S/C18H18O6/c1-22-15-7-11(3-4-14(15)21)17-13(9-20)12-5-10(8-19)6-16(23-2)18(12)24-17/h3-8,13,17,20-21H,9H2,1-2H3/t13-,17+/m1/s1
InChIKey	FHRVWMUANLCTEE-DYVFJYSZSA-N
Formula	C₁₈H₁₈O₆
HBA	6
HBD	2
MW	330.34
Rotatable Bonds	5
TPSA	85.22
LogP	2.43
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	330.11
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: 10496641

Cas: 321991-55-3

Zinc: ZINC000015215996

Nmrshiftdb2: 70129075

Chembl: CHEMBL2436614

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 330.34 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 330.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.72
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 69.01
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: 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: 7.24
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.95
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.04
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.94
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: 1.1
Rat (Acute): 2.0
Rat (Chronic Oral): 2.4
Fathead Minnow: 4.26
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 413.3
Hydration Free Energy: -9.22
Log(D) at pH=7.4: 1.96
Log(P): 1.19
Log S: -3.97
Log(Vapor Pressure): -7.57
Melting Point: 153.54
pKa Acid: 7.36
pKa Basic: 0.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9307
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9088
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8997
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8984
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8944
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8938
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8900
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8756
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8733
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8712
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8667
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8638
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8582
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8556
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8530
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8437
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8386
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8378
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8364
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8133
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8082
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7958
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7936
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7882
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7794
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7791
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7782
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7683
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7678
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7610
Glycerol kinase	P0A6F3	GLPK_ECOLI	Escherichia coli	4	0.7406
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7371
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7353
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7348
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7328
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.7319
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7295
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7278
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7278
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7245
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7237
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7179
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7139
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7138
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7126
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7101
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7070
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7061
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7056
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7032
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7030
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7025

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