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(+)-isolariciresinol

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	OC[C@@H]1Cc2cc(OC)c(cc2[C@@H]([C@H]1CO)c1ccc(c(c1)OC)O)O
InChI	InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/s1
InChIKey	OGFXBIXJCWAUCH-KPHUOKFYSA-N
Formula	C₂₀H₂₄O₆
HBA	6
HBD	4
MW	360.41
Rotatable Bonds	5
TPSA	99.38
LogP	2.02
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	360.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Lycium intricatum	Solanaceae	Plantae	343886

Showing of synonyms

Bendjedou H, Maggi F, et al. (2022). A new ionone derivative from Lycium intricatum Boiss. (Solanaceae). Natural product research, 2022, 36(3), 687-694. [View] [PubMed]

Pubchem: 160521

Cas: 548-29-8

Gnps: CCMSLIB00010007749

Zinc: ZINC000004104829

Chebi: 69542

Nmrshiftdb2: 60024959

Metabolights: MTBLC69542

Chembl: CHEMBL399512

Comptox: DTXSID20203273

Bindingdb: 50223783

CPRiL: 315355

SMILES: c1cccc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 360.41 g/mol

SMILES: C1CCCc(c12)cccc2

Level: 0

Mol. Weight: 360.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 360.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.21
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.160
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 74.34
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: 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: 13.020
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.250
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.000
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.470
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2.450
Rat (Acute): 2.100
Rat (Chronic Oral): 3.280
Fathead Minnow: 4.060
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 449.440
Hydration Free Energy: -9.840
Log(D) at pH=7.4: 1.980
Log(P): 0.62
Log S: -3.67
Log(Vapor Pressure): -8.03
Melting Point: 174.12
pKa Acid: 7.52
pKa Basic: 4.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9692
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9452
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8986
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8976
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8886
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8873
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8864
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8740
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8708
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8687
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8674
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8539
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8506
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8505
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8483
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8442
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.8337
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8328
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8178
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8144
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8126
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8107
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8105
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8080
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8068
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8061
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8039
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7933
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.7890
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7879
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7832
16S rRNA (adenine(1408)-N(1))-methyltransferase	A8C927	NPMA_ECOLX	Escherichia coli	4	0.7783
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7767
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7723
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7695
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7689
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7686
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7670
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7664
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7661
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7646
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7641
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7614
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7600
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7540
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7519
Ribosomal RNA small subunit methyltransferase Nep1	Q57977	NEP1_METJA	Methanocaldococcus jannaschii	4	0.7483
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7466
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7439
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7421
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7419
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7410
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7402
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7390
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7372
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7339
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7281
PTS system glucose-specific EIIA component	P69783	PTGA_ECOLI	Escherichia coli	3	0.7275
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7275
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7269
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7266
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7264
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7262
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7251
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7246
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7243
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7238
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7221
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7188
Poly(A) polymerase, putative	Q381M1	Q381M1_TRYB2	Trypanosoma brucei brucei	4	0.7175
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7170
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7169
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7163
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7153
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7150
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7147
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7146
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7146
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7141
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7136
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7136
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7126
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7113
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7105
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7084
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7070
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7065
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	2	0.7064
Type II methyltransferase M.HhaI	P05102	MTH1_HAEPH	Haemophilus parahaemolyticus	3	0.7057
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7052
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7049
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7032
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7023
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7005

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