15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A - Compound Card

15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A

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15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A

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)/COC1OC(COC(=O)Cc2ccc(cc2)O)C(C(C1O)O)O
InChI InChI=1S/C29H34O12/c1-15-24-20(32)9-17(12-30)3-2-4-18(10-21(24)40-28(15)37)13-39-29-27(36)26(35)25(34)22(41-29)14-38-23(33)11-16-5-7-19(31)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-32,34-36H,1-2,4,9,11,13-14H2/b17-3+,18-10-/t20-,21+,22?,24+,25?,26?,27?,29?/m0/s1
InChIKey NGDUYKZDYOOZLX-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 Sonchus asper Asteraceae Plantae 50193
2 Urospermum picroides Asteraceae Plantae 268113

Showing of synonyms

  • Helal AM, Nakamura N, et al. (2000). Sesquiterpene lactone glucosides from Sonchus asper. Phytochemistry,2000, 53,473-477. [View] [PubMed]
  • Balboul BAAA, Ahmed AA, et al. (1997). Sesquiterpene lactones and glycosides from Urospermum picroides. Phytochemistry,1997,45(2),369-373. [View]
Pubchem: 162876634

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OCC2CCCC(O2)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: c1ccccc1CC(=O)OCC2CCCCO2

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)
-6.13
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
38.75
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.78
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.85
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.36
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
-5781.58
Rat (Acute)
3.5
Rat (Chronic Oral)
3.22
Fathead Minnow
15.65
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
444.4
Hydration Free Energy
-2.93
Log(D) at pH=7.4
1.25
Log(P)
-0.06
Log S
-2.42
Log(Vapor Pressure)
-10.28
Melting Point
156.76
pKa Acid
5.56
pKa Basic
4.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8541
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8541
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8473
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8473
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8457
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8457
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8451
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8451
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7806
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7806
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7390
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7390
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7241
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7241
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7226
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7226
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7175
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7175
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7159
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7159
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7150
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7150

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