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1,5alpha-dihydroxypinoresinol

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1ccc(cc1O)C1OCC2(C1C(O)OC2c1ccc(c(c1)OC)O)O
InChI	InChI=1S/C20H22O8/c1-25-14-6-4-10(7-13(14)22)17-16-19(23)28-18(20(16,24)9-27-17)11-3-5-12(21)15(8-11)26-2/h3-8,16-19,21-24H,9H2,1-2H3
InChIKey	WGLGVPLRXITKFF-UHFFFAOYSA-N
Formula	C₂₀H₂₂O₈
HBA	8
HBD	4
MW	390.39
Rotatable Bonds	4
TPSA	117.84
LogP	1.62
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	390.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Premna odorata	Lamiaceae	Plantae	1037421

Showing of synonyms

Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 390.39 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 390.39 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 390.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 390.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.16
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.180
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.65

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 1.01
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: 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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.610
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.580
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.580
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.920
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: -10.470
Rat (Acute): 2.300
Rat (Chronic Oral): 3.060
Fathead Minnow: 4.240
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: 433.190
Hydration Free Energy: -8.350
Log(D) at pH=7.4: 1.870
Log(P): 0.86
Log S: -3.76
Log(Vapor Pressure): -7.58
Melting Point: 191.43
pKa Acid: 7.48
pKa Basic: 1.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9057
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8906
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8832
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8794
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8774
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8733
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8684
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8618
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8540
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8406
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8394
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	4	0.8253
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.8176
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8150
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8108
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7977
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7966
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7949
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.7938
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7894
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7868
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7803
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7778
Replicase polyprotein 1ab	P0C6X7	R1AB_CVHSA	Human SARS coronavirus	4	0.7769
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7740
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.7730
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7719
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7649
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7642
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7610
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7529
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7519
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.7488
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7454
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7424
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7416
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7413
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7383
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7337
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7310
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7306
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7297
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7273
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7263
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7258
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7250
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7249
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7241
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7230
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7228
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7218
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7208
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	4	0.7170
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7148
Kelch-like ECH-associated protein 1	Q14145	KEAP1_HUMAN	Homo sapiens	3	0.7144
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7143
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7138
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7125
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7124
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7107
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7098
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7088
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7085
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7071
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7057
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7056
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7046
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7030
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7016
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7009
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7006
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7003

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