8-O-(4-hydroxy)-tiglate - Compound Card

8-O-(4-hydroxy)-tiglate

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8-O-(4-hydroxy)-tiglate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC/C=C(/C(=O)O[C@@H]1C[C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2[C@H](C1=C)C[C@@H]([C@]2(O)CCl)O)\C
InChI InChI=1S/C20H25ClO7/c1-9(4-5-22)18(24)27-14-6-13-11(3)19(25)28-17(13)16-12(10(14)2)7-15(23)20(16,26)8-21/h4,12-17,22-23,26H,2-3,5-8H2,1H3/b9-4+/t12-,13-,14+,15-,16-,17-,20+/m0/s1
InChIKey BAIQQBIVSWTQNT-ZCEBHBKASA-N
Formula C20H25ClO7
HBA 7
HBD 3
MW 412.87
Rotatable Bonds 4
TPSA 113.29
LogP 0.86
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 412.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea scoparia Asteraceae Plantae 2072395

Showing of synonyms

  • Youssef D, Frahm A.W. (1994). Constituents of the Egyptian Centaurea scoparia; chlorinated guaianolides of the aerial parts.. Planta medica, 1994, 60(3), 267-71. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CCC3)C(=C)CC2

Level: 0

Mol. Weight: 412.87 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.540
Plasma Protein Binding
54.39
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
8.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.480
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.580
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.770
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-8.520
Rat (Acute)
3.870
Rat (Chronic Oral)
2.440
Fathead Minnow
4.000
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
438.100
Hydration Free Energy
-7.800
Log(D) at pH=7.4
1.390
Log(P)
1.3
Log S
-2.85
Log(Vapor Pressure)
-9.26
Melting Point
151.09
pKa Acid
6.69
pKa Basic
4.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8716
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7901
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7632
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7572
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7507
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7409
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7308

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