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Echiumin A

Family: Plantae - Boraginaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Dihydronaphthalene Lignan

Canonical Smiles	OC[C@@]1(O[C@H]2O[C@H](COC(=O)/C=C/c3ccc(cc3)O[C@@H]3O[C@H](C)[C@H]([C@@H]([C@@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)O[C@H]2[C@H]([C@@H]1OC(=O)[C@H]1C(=Cc3c([C@H]1c1ccc(c(c1)OC)O)c(OC)c(c(c3)OC)O)C(=O)OC2)O
InChI	InChI=1S/C48H54O24/c1-19-34(52)38(56)40(58)46(67-19)68-23-9-5-20(6-10-23)7-12-30(51)65-16-28-35(53)39(57)41(59)47(69-28)72-48(18-49)43-37(55)29(71-48)17-66-44(60)24-13-22-15-27(63-3)36(54)42(64-4)32(22)31(33(24)45(61)70-43)21-8-11-25(50)26(14-21)62-2/h5-15,19,28-29,31,33-35,37-41,43,46-47,49-50,52-59H,16-18H2,1-4H3/b12-7+/t19-,28-,29-,31-,33+,34-,35-,37-,38+,39+,40+,41-,43+,46+,47-,48+/m1/s1
InChIKey	SGDPGUPDOPRAOL-KUJCZWEWSA-N
Formula	C₄₈H₅₄O₂₄
HBA	24
HBD	10
MW	1014.94
Rotatable Bonds	13
TPSA	355.04
LogP	-1.53
Number Rings	8
Number Aromatic Rings	3
Heavy Atom Count	72
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	1014.3
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Echium angustifolium	Boraginaceae	Plantae	543570

Showing of synonyms

El-Rokh A.R, Negm A, et al. (2018). Sucrose diester of aryldihydronaphthalene-type lignans from Echium angustifolium Mill. and their antitumor activity. Phytochemistry, 2018, 149, 155-160. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)ccc2C=CC(=O)OCC3CCCC(O3)OC(C45)OC(C4)COC(=O)C=6C(C(=O)O5)C(c7c(C6)cccc7)c8ccccc8

Level: 4

Mol. Weight: 1014.94 g/mol

SMILES: O1CCCCC1Oc(cc2)ccc2C=CC(=O)OCC3CCCC(O3)OC(C45)OC(C4)COC(=O)C=6C(C(=O)O5)Cc7c(C6)cccc7

Level: 3

Mol. Weight: 1014.94 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(C34)OC(C3)COC(=O)C=5C(C(=O)O4)C(c6c(C5)cccc6)c7ccccc7

Level: 3

Mol. Weight: 1014.94 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(C34)OC(C3)COC(=O)C=5C(C(=O)O4)Cc6c(C5)cccc6

Level: 2

Mol. Weight: 1014.94 g/mol

SMILES: O1CCCCC1OC(C23)OC(C2)COC(=O)C=4C(C(=O)O3)C(c5c(C4)cccc5)c6ccccc6

Level: 2

Mol. Weight: 1014.94 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 1014.94 g/mol

SMILES: O1CCCCC1OC(C23)OC(C2)COC(=O)C=4C(C(=O)O3)Cc5c(C4)cccc5

Level: 1

Mol. Weight: 1014.94 g/mol

SMILES: C12CC(OC1)COC(=O)C=3C(C(=O)O2)C(c4c(C3)cccc4)c5ccccc5

Level: 1

Mol. Weight: 1014.94 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1014.94 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 1014.94 g/mol

SMILES: C12CC(OC1)COC(=O)C=3C(C(=O)O2)Cc4c(C3)cccc4

Level: 0

Mol. Weight: 1014.94 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1014.94 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1014.94 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 108496.7
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 14180073.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 57.96
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: Inhibitor

Excretion

Clearance: 4.26
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -329790.23
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.55
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
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: Safe
T. Pyriformis: -25736152997.46
Rat (Acute): 2.85
Rat (Chronic Oral): 57.16
Fathead Minnow: 32486381.49
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 2894595700.83
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1599.36
Log(P): -1.39
Log S: -5.05
Log(Vapor Pressure): -95317496.73
Melting Point: 299.82
pKa Acid: -694465.37
pKa Basic: -5566.44

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9173
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8881
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8538
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.8421
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8339
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8263
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8215
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8177
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7949
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7902
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7848
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7649
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7640
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7506
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7492
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7371
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7354
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7333
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7318
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7317
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7312
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7272
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7258
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7219
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7192
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	3	0.7182
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.7145
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7112
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7050
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7045
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7030

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