Urospermal A - Compound Card

Urospermal A

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Urospermal A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=C\CC1)/C=O)O
InChI InChI=1S/C15H18O5/c1-9-14-12(18)5-10(7-16)3-2-4-11(8-17)6-13(14)20-15(9)19/h3,6-7,12-14,17-18H,1-2,4-5,8H2/b10-3+,11-6-/t12-,13+,14+/m0/s1
InChIKey CVISOHZWXIVDFN-SLQKEEQISA-N
Formula C15H18O5
HBA 5
HBD 2
MW 278.3
Rotatable Bonds 2
TPSA 83.83
LogP 0.67
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 278.12
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

  • Salam NAA, Mahmoud ZF, et al. (1982). A glucoside of urospermal A. Phytochemistry,1982,21(11),2746-2747. [View]
  • Balboul BAAA, Ahmed AA, et al. (1997). Sesquiterpene lactones and glycosides from Urospermum picroides. Phytochemistry,1997,45(2),369-373. [View]
Pubchem: 14287067
Nmrshiftdb2: 60147098

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 278.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.3
Plasma Protein Binding
37.37
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
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
3.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.11
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.33
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.78
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
1.33
Rat (Acute)
4.23
Rat (Chronic Oral)
1.58
Fathead Minnow
3.97
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
372.86
Hydration Free Energy
-11.28
Log(D) at pH=7.4
0.34
Log(P)
-0.16
Log S
-1.41
Log(Vapor Pressure)
-7.07
Melting Point
136.88
pKa Acid
5.69
pKa Basic
4.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8619
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8619
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8091
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8091
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7762
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7762
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7524
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7524

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