Sweroside - Compound Card

Sweroside

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Sweroside

Structure
Zoomed Structure
  • Family: Plantae - Gentianaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid
Canonical Smiles C=C[C@H]1[C@@H](OC=C2[C@H]1CCOC2=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1
InChIKey VSJGJMKGNMDJCI-ZASXJUAOSA-N
Formula C16H22O9
HBA 9
HBD 4
MW 358.34
Rotatable Bonds 4
TPSA 134.91
LogP -1.59
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 358.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurium spicatum Gentianaceae Plantae 172074

Showing of synonyms

  • El-Shanawany MA, Mohamed GA, et al. (2011). A new xanthone from the roots of Centaurium spicatum. Phytochemistry Letters,2011,4,126-128. [View]
Pubchem: 161036
Kegg Ligand: C17071
Chebi: 80907
Nmrshiftdb2: 20170549
Bindingdb: 50279544
CPRiL: 61001
Structure

SMILES: O=C1OCCC(C1=2)CC(OC2)OC3CCCCO3

Level: 1

Mol. Weight: 358.34 g/mol

Structure

SMILES: C1OCCC(C=12)CCOC2=O

Level: 0

Mol. Weight: 358.34 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 358.34 g/mol

Antimicrobial
Antiprotozoal
Cytotoxicity

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.03
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
42.75
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.42
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.47
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
-7.02
Rat (Acute)
2.78
Rat (Chronic Oral)
3.06
Fathead Minnow
3.75
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
444.16
Hydration Free Energy
-14.27
Log(D) at pH=7.4
-0.17
Log(P)
-1.45
Log S
-1.31
Log(Vapor Pressure)
-12.77
Melting Point
169.28
pKa Acid
5.46
pKa Basic
4.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.9170
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.9170
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8114
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8114
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7892
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7892
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7457
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7457
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7367
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7367

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