Urospermal A 15-O-beta-glucoside - Compound Card

Urospermal A 15-O-beta-glucoside

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Urospermal A 15-O-beta-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Glycoside
Canonical Smiles O=C/C/1=C/CC/C(=C/[C@@H]2[C@@H]([C@H](C1)O)C(=C)C(=O)O2)/CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C21H28O10/c1-10-16-13(24)5-11(7-22)3-2-4-12(6-14(16)30-20(10)28)9-29-21-19(27)18(26)17(25)15(8-23)31-21/h3,6-7,13-19,21,23-27H,1-2,4-5,8-9H2/b11-3+,12-6-/t13-,14+,15+,16+,17+,18-,19+,21+/m0/s1
InChIKey SMIZUXPJPXRGOS-XWCSJVOGSA-N
Formula C21H28O10
HBA 10
HBD 5
MW 440.45
Rotatable Bonds 5
TPSA 162.98
LogP -1.5
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 440.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Urospermum picroides Asteraceae Plantae 268113
2 Urospermum picroides Asteraceae Plantae 268113

Showing of synonyms

  • Balboul BAAA, Ahmed AA, et al. (1997). Sesquiterpene lactones and glycosides from Urospermum picroides. Phytochemistry,1997,45(2),369-373. [View]
  • Amer MMA, Salama OM, et al. (1984). Urospermal, a glucoside from Urospermum picroides. Phytochemistry,1984,23(3),692-693. [View]
Pubchem: 23983719
Nmrshiftdb2: 60046511

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=C(CCC=CCC2)COC3CCCCO3

Level: 1

Mol. Weight: 440.45 g/mol

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 440.45 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 440.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
44.85
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
3.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.49
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.37
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
-42.49
Rat (Acute)
3.34
Rat (Chronic Oral)
2.87
Fathead Minnow
3.99
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
531.95
Hydration Free Energy
-5.33
Log(D) at pH=7.4
-0.04
Log(P)
-1.75
Log S
-0.85
Log(Vapor Pressure)
-13.87
Melting Point
151.58
pKa Acid
5.12
pKa Basic
4.95

No predicted protein targets found for this compound.

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