Arctolide - Compound Card

Arctolide

Select a section from the left sidebar

Arctolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C[C@@H]2[C@@](C1=C)(O)C[C@H]1[C@H](C[C@]32CO3)OC(=O)C1=C
InChI InChI=1S/C17H20O6/c1-8-11-5-17(20)9(2)12(22-10(3)18)4-14(17)16(7-21-16)6-13(11)23-15(8)19/h11-14,20H,1-2,4-7H2,3H3/t11-,12+,13+,14+,16-,17-/m1/s1
InChIKey XRCCPOSHMKZPFI-IHFPKREYSA-N
Formula C17H20O6
HBA 6
HBD 1
MW 320.34
Rotatable Bonds 1
TPSA 85.36
LogP 0.89
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 320.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Arctotis grandis Asteraceae Plantae 41478
2 Venidium fastuosum Asteraceae Plantae 259861

Showing of synonyms

  • Halim AF, Zaghloul AM, et al. (1983). Further guaianolides from Arctotis grandis.. Phytochemistry,1983,22(6),1510-1512.. [View]
  • Ali AA, El-Emary NA, et al. (1992). Guaianolides from Venidium fastuosum. Phytochemistry,1992,31(8),2781-2784. [View]
Pubchem: 442144
Kegg Ligand: C09298
Chebi: 2811
Nmrshiftdb2: 70053259

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C2)C1CC(C(=C)CC3)C3C24CO4

Level: 0

Mol. Weight: 320.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.23
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.18
Plasma Protein Binding
24.89
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.66
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.63
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.22
Rat (Acute)
4.36
Rat (Chronic Oral)
1.75
Fathead Minnow
3.92
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
366.44
Hydration Free Energy
-6.17
Log(D) at pH=7.4
0.02
Log(P)
0.27
Log S
-1.93
Log(Vapor Pressure)
-6.7
Melting Point
131.43
pKa Acid
5.31
pKa Basic
4.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9149
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9149
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8316
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8316
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8061
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8061
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7952
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7952
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7636
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7636
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7485
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7485
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7036
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7036
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7016
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7016

Download SDF