8-desacetylcentaurepensin-8-O-(4-hydroxytiglinate) - Compound Card

8-desacetylcentaurepensin-8-O-(4-hydroxytiglinate)

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8-desacetylcentaurepensin-8-O-(4-hydroxytiglinate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/C=C(/C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)[C@@]([C@H](C2)O)(O)CCl)\C
InChI InChI=1S/C20H25ClO7/c1-9(4-5-22)18(24)27-13-6-10(2)12-7-14(23)20(26,8-21)16(12)17-15(13)11(3)19(25)28-17/h4,12-17,22-23,26H,2-3,5-8H2,1H3/b9-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1
InChIKey QYDZDLCERJLVOK-LRJNHNEYSA-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

  • Helal AM, Nakamura N, et al. (1997). Guaianolides from Centaurea scoparia. Phytochemistry,1997,45(3),551-554. [View]
Pubchem: 6442949

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)
-4.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
53.85
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.600
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.460
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.570
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.460
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
-7.590
Rat (Acute)
4.080
Rat (Chronic Oral)
2.410
Fathead Minnow
4.020
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
444.390
Hydration Free Energy
-8.070
Log(D) at pH=7.4
1.250
Log(P)
0.92
Log S
-2.82
Log(Vapor Pressure)
-9.21
Melting Point
149.19
pKa Acid
7.01
pKa Basic
4.8
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 0.8346
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8346
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7284
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7284
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7224
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7224

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