Echiumin B - Compound Card

Echiumin B

Select a section from the left sidebar

Echiumin B

Structure
Zoomed Structure
  • 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(cc1)O)c(OC)c(c(c3)OC)O)C(=O)OC2)O
InChI InChI=1S/C47H52O23/c1-19-33(51)37(55)39(57)45(65-19)66-24-11-4-20(5-12-24)6-13-29(50)63-16-27-34(52)38(56)40(58)46(67-27)70-47(18-48)42-36(54)28(69-47)17-64-43(59)25-14-22-15-26(61-2)35(53)41(62-3)31(22)30(32(25)44(60)68-42)21-7-9-23(49)10-8-21/h4-15,19,27-28,30,32-34,36-40,42,45-46,48-49,51-58H,16-18H2,1-3H3/b13-6+/t19-,27-,28-,30-,32+,33-,34-,36-,37+,38+,39+,40-,42+,45+,46-,47+/m1/s1
InChIKey IDYYTYVOBPSDGD-DOKJCNIZSA-N
Formula C47H52O23
HBA 23
HBD 10
MW 984.91
Rotatable Bonds 12
TPSA 345.81
LogP -1.54
Number Rings 8
Number Aromatic Rings 3
Heavy Atom Count 70
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 984.29
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.

Structure

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: 984.91 g/mol

Structure

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: 984.91 g/mol

Structure

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: 984.91 g/mol

Structure

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

Level: 2

Mol. Weight: 984.91 g/mol

Structure

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

Level: 2

Mol. Weight: 984.91 g/mol

Structure

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

Level: 2

Mol. Weight: 984.91 g/mol

Structure

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

Level: 1

Mol. Weight: 984.91 g/mol

Structure

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

Level: 1

Mol. Weight: 984.91 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 984.91 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 984.91 g/mol

Structure

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

Level: 0

Mol. Weight: 984.91 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 984.91 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 984.91 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.46
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
43900.22
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5738081.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
62.68
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
3.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-133449.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.69
Liver Injury II
Toxic
hERG Blockers
Toxic
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
-10414339663.39
Rat (Acute)
2.99
Rat (Chronic Oral)
24.07
Fathead Minnow
13145896.14
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
1171317241.17
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-639.71
Log(P)
-0.9
Log S
-4.74
Log(Vapor Pressure)
-38570804.78
Melting Point
293.69
pKa Acid
-280974.74
pKa Basic
-2242.11
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 0.9174
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8889
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8799
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8781
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8770
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8744
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8711
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8617
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8513
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8446
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8439
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8287
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8278
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8145
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8097
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8056
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8013
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7994
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7936
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7848
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7811
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7778
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7727
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7693
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7691
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7643
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7615
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7567
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7494
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7446
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7423
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7402
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7393
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7389
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7361
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7360
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7353
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7347
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7325
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7311
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7268
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7258
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7201
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7102
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7074
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7070
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7060
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7047
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7021

Download SDF