Urospermal A-15-O-[4'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranoside - Compound Card

Urospermal A-15-O-[4'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranoside

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Urospermal A-15-O-[4'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Glycoside
Canonical Smiles OCC1OC(OC/C/2=C\[C@H]3OC(=O)C(=C)[C@@H]3[C@H](C/C(=C\CC2)/C=O)O)C(C(C1OC(=O)Cc1ccc(cc1)O)O)O
InChI InChI=1S/C29H34O12/c1-15-24-20(33)9-17(12-30)3-2-4-18(10-21(24)39-28(15)37)14-38-29-26(36)25(35)27(22(13-31)40-29)41-23(34)11-16-5-7-19(32)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-33,35-36H,1-2,4,9,11,13-14H2/b17-3+,18-10-/t20-,21+,22?,24+,25?,26?,27?,29?/m0/s1
InChIKey SNCOMGZHOXWALF-NENSKQIUSA-N
Formula C29H34O12
HBA 12
HBD 5
MW 574.58
Rotatable Bonds 8
TPSA 189.28
LogP -0.0
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 574.21
Number of Lipinski Rule Violations 2
# 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]
  • Amer MMA, Salama OM, et al. (1984). Urospermal, a glucoside from Urospermum picroides. Phytochemistry,1984,23(3),692-693. [View]
Pubchem: 162816841
Nmrshiftdb2: 70059558

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OC2CCC(OC2)OCC(=CC(C34)OC(=O)C3=C)CCC=CCC4

Level: 2

Mol. Weight: 574.58 g/mol

Structure

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

Level: 1

Mol. Weight: 574.58 g/mol

Structure

SMILES: C1OCCCC1OC(=O)Cc2ccccc2

Level: 1

Mol. Weight: 574.58 g/mol

Structure

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

Level: 0

Mol. Weight: 574.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 574.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 574.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.01
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
35.34
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.58
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.82
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.38
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
-5898.29
Rat (Acute)
3.51
Rat (Chronic Oral)
3.23
Fathead Minnow
15.9
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
437.68
Hydration Free Energy
-2.93
Log(D) at pH=7.4
1.11
Log(P)
0.03
Log S
-2.42
Log(Vapor Pressure)
-10.22
Melting Point
153.04
pKa Acid
5.22
pKa Basic
3.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8748
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8748
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.8693
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.8693
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7391
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7391
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7207
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7207
Sensor histidine kinase EnvZ P0AEJ4 ENVZ_ECOLI Escherichia coli 3 0.7129
Sensor histidine kinase EnvZ P0AEJ4 ENVZ_ECOLI Escherichia coli 3 0.7129
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7104
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7104
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7083
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7083
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7062
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7062
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7012
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7012

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