8alpha,4'-(hydroxytiglinate)-8-desacyloxysubluteolide - Compound Card

8alpha,4'-(hydroxytiglinate)-8-desacyloxysubluteolide

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8alpha,4'-(hydroxytiglinate)-8-desacyloxysubluteolide

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@@]1([C@H](C2)O)OC1)\C
InChI InChI=1S/C20H24O7/c1-9(4-5-21)18(23)26-13-6-10(2)12-7-14(22)20(8-25-20)16(12)17-15(13)11(3)19(24)27-17/h4,12-17,21-22H,2-3,5-8H2,1H3/b9-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1
InChIKey LWDKIUHKLIZGEF-LRJNHNEYSA-N
Formula C20H24O7
HBA 7
HBD 2
MW 376.41
Rotatable Bonds 3
TPSA 105.59
LogP 0.66
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 376.15
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]

No compound-protein relationship available.

Structure

SMILES: O1CC12C3C4C(C(=C)C(=O)O4)CCC(=C)C3CC2

Level: 0

Mol. Weight: 376.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.300
Plasma Protein Binding
30.51
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
14.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.850
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.700
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
-8.690
Rat (Acute)
5.080
Rat (Chronic Oral)
2.130
Fathead Minnow
3.960
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
431.950
Hydration Free Energy
-7.010
Log(D) at pH=7.4
0.370
Log(P)
0.45
Log S
-2.51
Log(Vapor Pressure)
-8.23
Melting Point
154.95
pKa Acid
5.72
pKa Basic
3.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7180
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7180

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