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Leucoseptoside A

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	OCC1O[C@@H](OCCc2ccc(c(c2)O)O)[C@H](C([C@@H]1OC(=O)/C=C/c1ccc(c(c1)OC)O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)O
InChI	InChI=1S/C30H38O15/c1-14-23(36)24(37)25(38)30(42-14)45-28-26(39)29(41-10-9-16-3-6-17(32)19(34)11-16)43-21(13-31)27(28)44-22(35)8-5-15-4-7-18(33)20(12-15)40-2/h3-8,11-12,14,21,23-34,36-39H,9-10,13H2,1-2H3/b8-5+/t14?,21?,23-,24-,25?,26-,27+,28?,29+,30-/m0/s1
InChIKey	ZMYQRHSOVRDQDL-OUXCIPJHSA-N
Formula	C₃₀H₃₈O₁₅
HBA	15
HBD	8
MW	638.62
Rotatable Bonds	11
TPSA	234.29
LogP	-0.71
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	638.22
Number of Lipinski Rule Violations	3

#	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]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4

Level: 3

Mol. Weight: 638.62 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OCCc3ccccc3

Level: 2

Mol. Weight: 638.62 g/mol

SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 638.62 g/mol

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 638.62 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 638.62 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 638.62 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 638.62 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 638.62 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 638.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.76
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.04
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 17.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 47.64
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: Non-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: 12.65
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.82
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.29
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: -32913.55
Rat (Acute): 2.21
Rat (Chronic Oral): 4.32
Fathead Minnow: 59.56
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 415.29
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.79
Log(P): 0.18
Log S: -4.2
Log(Vapor Pressure): -15.89
Melting Point: 179.45
pKa Acid: 5.24
pKa Basic: 3.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9417
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9130
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8821
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8802
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8566
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8504
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8495
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8376
Beta-galactoside-specific lectin 1	P81446	ML1_VISAL	Viscum album	3	0.8263
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8230
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8189
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8156
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8093
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8080
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8020
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7781
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7760
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7699
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7627
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7621
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7614
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7597
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7590
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7397
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7358
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7328
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7273
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7218
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7209
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7178
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7174
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7153
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7152
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7152
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7140
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7140
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7110
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7092
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7085
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7062
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7043
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7024
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7013
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7005
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7005
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7004
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7000

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