8-desacylrepin - Compound Card

8-desacylrepin

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8-desacylrepin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C[C@H](O)[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H]([C@]13OC1)O)OC(=O)C2=C
InChI InChI=1S/C15H18O5/c1-6-3-9(16)11-7(2)14(18)20-13(11)12-8(6)4-10(17)15(12)5-19-15/h8-13,16-17H,1-5H2/t8-,9-,10-,11+,12-,13-,15+/m0/s1
InChIKey PJBBLXOPECXDHO-YWDFAVMRSA-N
Formula C15H18O5
HBA 5
HBD 2
MW 278.3
Rotatable Bonds 0
TPSA 79.29
LogP 0.17
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 278.12
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: 101705724

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 278.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.25
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.14
Plasma Protein Binding
23.18
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
14.08
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.73
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.36
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
-0.05
Rat (Acute)
4.27
Rat (Chronic Oral)
1.81
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
378.59
Hydration Free Energy
-8.95
Log(D) at pH=7.4
-0.6
Log(P)
0.04
Log S
-1.55
Log(Vapor Pressure)
-7.3
Melting Point
163.93
pKa Acid
5.08
pKa Basic
3.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9232
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9232
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8035
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8035
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7222
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7222
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7113
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7113
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7029
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7029

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