Echiumin C - Compound Card

Echiumin C

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Echiumin C

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Dihydronaphthalene Lignan
Canonical Smiles OC[C@H]1O[C@H](O[C@]2(CO)O[C@@H]([C@H]([C@@H]2O)O)COC(=O)C2=Cc3cc(OC)c(c(c3[C@H]([C@H]2C(=O)OC)c2ccc(cc2)O)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C33H40O18/c1-45-17-9-14-8-16(22(31(44)47-3)20(13-4-6-15(36)7-5-13)21(14)28(46-2)24(17)38)30(43)48-11-19-25(39)29(42)33(12-35,50-19)51-32-27(41)26(40)23(37)18(10-34)49-32/h4-9,18-20,22-23,25-27,29,32,34-42H,10-12H2,1-3H3/t18-,19-,20-,22+,23-,25-,26+,27-,29+,32-,33+/m1/s1
InChIKey HXUARCVCNWOOOP-HWWKUVKWSA-N
Formula C33H40O18
HBA 18
HBD 9
MW 724.67
Rotatable Bonds 11
TPSA 280.82
LogP -2.4
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 724.22
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: c1ccccc1C(c(c23)cccc3)CC(=C2)C(=O)OCC4CCC(O4)OC5CCCCO5

Level: 3

Mol. Weight: 724.67 g/mol

Structure

SMILES: c1cccc(c12)CCC(=C2)C(=O)OCC3CCC(O3)OC4CCCCO4

Level: 2

Mol. Weight: 724.67 g/mol

Structure

SMILES: O1CCCC1COC(=O)C(=C2)CC(c(c23)cccc3)c4ccccc4

Level: 2

Mol. Weight: 724.67 g/mol

Structure

SMILES: O1CCCC1COC(=O)C(=C2)CCc(c23)cccc3

Level: 1

Mol. Weight: 724.67 g/mol

Structure

SMILES: c1cccc(c12)C(CC=C2)c3ccccc3

Level: 1

Mol. Weight: 724.67 g/mol

Structure

SMILES: O1CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 724.67 g/mol

Structure

SMILES: C1=CCCc(c12)cccc2

Level: 0

Mol. Weight: 724.67 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 724.67 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 724.67 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 724.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.4
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-2.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
401.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
60.09
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
4.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-6.190
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.300
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
-726380.050
Rat (Acute)
2.670
Rat (Chronic Oral)
4.600
Fathead Minnow
928.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
75075.500
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.320
Log(P)
-0.97
Log S
-4.14
Log(Vapor Pressure)
-2464.65
Melting Point
205.39
pKa Acid
0.1
pKa Basic
3.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9561
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9172
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8804
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8660
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8644
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8617
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8572
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8490
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8436
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8410
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8268
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8239
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8236
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8235
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8187
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8132
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8098
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8044
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7940
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7844
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7818
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7806
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7786
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7768
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7700
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7648
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7611
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7580
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7486
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7484
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7469
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7434
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7401
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7348
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7333
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7329
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7329
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7313
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7309
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7263
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7245
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7235
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7228
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7206
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7197
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7187
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7179
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7179
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7178
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7158
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7143
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7116
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7094
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7057
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7037
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 4 0.7027
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7017
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7002

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