2,3-dihydro-3beta-hydroxyeuparin 3-O-glucopyranoside - Compound Card

2,3-dihydro-3beta-hydroxyeuparin 3-O-glucopyranoside

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2,3-dihydro-3beta-hydroxyeuparin 3-O-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Benzofuran
Canonical Smiles OCC1O[C@@H](O[C@@H]2[C@H](Oc3c2cc(C(=O)C)c(c3)O)C(=C)C)C([C@H]([C@H]1O)O)O
InChI InChI=1S/C19H24O9/c1-7(2)17-18(10-4-9(8(3)21)11(22)5-12(10)26-17)28-19-16(25)15(24)14(23)13(6-20)27-19/h4-5,13-20,22-25H,1,6H2,2-3H3/t13?,14-,15-,16?,17+,18-,19-/m0/s1
InChIKey ZUUUPZVQBJSGEX-LTGUEROJSA-N
Formula C19H24O9
HBA 9
HBD 5
MW 396.39
Rotatable Bonds 5
TPSA 145.91
LogP -0.21
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 396.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio glaucus Asteraceae Plantae 121546

Showing of synonyms

  • Zaher A.M, Sultan R, et al. (2022). New antimicrobial and cytotoxic benzofuran glucoside from Senecio glaucus L. Natural product research, 2022, 36(1), 136-141. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OCC2OC3CCCCO3

Level: 1

Mol. Weight: 396.39 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 396.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 396.39 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.75
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
64.86
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
7.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.08
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.96
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
-8.38
Rat (Acute)
2.36
Rat (Chronic Oral)
3.68
Fathead Minnow
4.11
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
476.42
Hydration Free Energy
-12.58
Log(D) at pH=7.4
1.08
Log(P)
0.63
Log S
-2.5
Log(Vapor Pressure)
-11.48
Melting Point
175.95
pKa Acid
6.02
pKa Basic
5.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9083
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8498
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8340
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8080
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7848
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7846
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7813
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7779
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7645
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7522
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7436
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7224
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7212
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7163
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7159
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7153
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7145
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7144
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7108
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7102
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7069
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7029

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